Dress shirts are one of the most important style basics in any wardrobe. While many men own dress shirts, they often struggle to make them work seamlessly with the rest of their outfits. Over the years, we’ve gained valuable insights into what makes a dress shirt truly versatile and essential. If we were to start from scratch, we’d recommend these 10 foundational dress shirts that every man should own. 

Dress shirts are fundamental to a classic man’s wardrobe, yet they often receive less attention than suits, shoes, or accessories. Selecting the right dress shirts is essential, as poorly chosen ones can be challenging to coordinate and may remain unworn—which we certainly want to avoid because each purchase should be worthwhile and must serve its purpose.

With these considerations in mind, let’s explore the best dress shirts for men to establish a versatile wardrobe foundation, ensuring preparedness for various style scenarios with a minimal yet impactful investment.

Dress Shirt Details to know

Men’s Dress Shirt Guide – Fit, Collar, Cuffs & Details

A quick reference for essential dress shirt details that will help you make informed decisions when selecting different types of shirts. Understanding aspects like fit, collar styles, cuff types, and other design details allows you to choose shirts that best suit your needs and preferences.

Check this dress shirt guide first!

Essential Long Sleeve Dress Shirts for Men: Formal

1. White Dress Shirts

Choose a Plain Weave White Dress Shirt as Your Wardrobe Staple

Opt for a medium spread collar and barrel cuffs for versatility

A white dress shirt in plain woven fabric is the cornerstone of a formal wardrobe. We recommend choosing a medium spread collar and barrel cuffs for maximum versatility. This combination allows the shirt to work well in formal and casual settings, pairing seamlessly with jeans or a formal business suit.

While cufflinks add a touch of elegance, they require a double cuff or French cuff. For your first shirt, it’s best to skip this additional expense and focus on building a practical wardrobe with barrel cuffs.

Select a medium-weight fabric for year-round wear

To make a plain weave dress shirt even more adaptable, opt for a medium-weight fabric suitable for year-round wear. A lighter fabric would be too specific to summer, while a heavier one would be limited to colder months. With a medium-weight option, you get a shirt that covers various occasions throughout the year.

Go for a French placket and skip the pocket for a clean look

For the placket, a French style is ideal. Sewn underneath the buttons, the neat seam gives a streamlined look without extra fabric.

We also suggest skipping the pocket, as shirt pockets are rarely used and can detract from the clean appearance.

Many off-the-rack options may come with pockets, but when you have the opportunity to go custom dress shirts, it’s best to opt for a pocket-free design.

If you’re looking for something low-maintenance, consider non-iron dress shirts from Eton. These wrinkle-free dress shirts are perfect for busy professionals or frequent travelers.

Go for a Fancy Weave for an Elegant White Dress Shirt Option

The fancy weave white dress shirt is an elegant option to your white dress shirt collection, with a refined, textured pattern. Best worn as a French cuff shirt, it’s an ideal choice for formal occasions where you want to add a subtle twist to classic white.

We love dress shirts that stand out due to a subtle waffle pattern weave, which sets them apart from a plain weave. When viewed closely and in the right lighting, the pattern adds depth, but from a distance, it appears as a solid white shirt with an appealing texture.

Consider a standard placket for variety

As with other formal men’s white dress shirt options, it’s best to skip the pocket to maintain a sleek appearance. If you went with a French placket before, go with a shirt placket this time simply so you have a range of different things in your wardrobe. A shirt placket creates a symmetrical look, especially if you wear a bow tie. However, for necktie wearers, the placket style is less crucial since the tie covers it.

Try Herringbone as an alternative to waffle weave

If the waffle weave doesn’t appeal to you, a fine herringbone pattern is another classic and timeless choice. Whichever weave you choose, opt for a medium spread collar. This collar style suits all face shapes and works well with tie knots and bow ties. It also looks polished when worn open for a more relaxed appearance.

EDITOR’S PICK FOR WHITE DRESS SHIRTS

THE NON-IRON STRETCH SHIRT

Why we recommend this:

The non-iron finish keeps it crisp throughout the day, and the slight stretch adds comfort. It also offers customizable options for the collar, cuff, pocket, and placket to suit personal style preferences.

Image Credit: Proper Cloth

2. Ivory Dress Shirt

The ivory dress shirt offers a subtle yet essential variation from plain white. When held side by side, the difference is clear, but on its own, it remains understated.

Ideal Color Pairings for Ivory

While plain white dress shirts pair best with dark hues such as black, dark green, navy, or charcoal, they can appear too stark when matched with warmer colors like brown or earthy tones. This is where the ivory shirt excels.

You can pair ivory shirts with…

Dark hues and warm tones

Ivory dress shirts provide a softer contrast that complements tweed and warmer shades effortlessly, making it a versatile choice for business and casual settings. An ivory shirt pairs beautifully with a charcoal or navy business suit but also fits seamlessly with summer suits or outfits featuring warmer tones.

Choosing the Right Cuffs

For the cuffs, your choice depends on how you plan to wear the shirt. If you frequently use cufflinks, opt for a French cuff. Otherwise, a barrel cuff is a more practical option that balances formality with everyday wear. Once your wardrobe basics are in place, the ivory dress shirt becomes an ideal travel companion.

3. Blue/Light Blue Dress Shirts

Choose a Light Blue Dress Shirt in Plain Weave

A blue dress shirt is a must-have because of its universal appeal and versatility. Unlike white, which can sometimes feel stark, light blue adds a hint of color that complements almost every suit color, from navy to gray.

Similar to the white dress shirts, we recommend getting your first light blue dress shirt in a medium-weight fabric, preferably in a plain weave. This weight ensures that the shirt is suitable for various occasions throughout the year.

Again, choose barrel cuffs for a practical and versatile option, and opt for a pocket-free, french placket dress shirt to maintain a clean and streamlined appearance.

Select a versatile shade of light blue

When selecting the shade of light blue, keep in mind that there are countless variations. A pastel or lighter shade of blue is a great starting point, as it offers maximum versatility. The softer hue of blue pairs effortlessly with both formal suits and more casual outfits, making it an essential piece in any classic wardrobe.

Consider a Twill Weave Blue Dress Shirt for Texture and Durability

For a distinctive yet classic addition to your wardrobe, consider a twill weave blue dress shirt. You can choose a darker or lighter shade, but make sure it differs from your existing light blue options. The twill weave features a subtle diagonal pattern, which enhances the fabric’s durability and resistance to wrinkles. This structure allows the fabric to drape well, offering a polished look for the wearer.

In addition, a blue dress shirt in twill weave works particularly well in a slightly heavier weight and is ideal for colder months. It also provides seasonal variety. Conversely, consider lighter-weight fabrics to stay comfortable if you live in a tropical or warm climate.

Experiment with double cuffs and a larger collar

Double cuffs are the best choice for this shirt. This is also an opportunity to experiment with tailored dress shirts. Go for a slightly larger collar rather than a small one. If your previous light blue shirt features barrel cuffs, opting for a French cuff here will give you greater versatility and a better sense of style.

EDITOR’S PICK FOR BLUE DRESS SHIRTS

CANALI LIGHT BLUE TWILL DRESS SHIRT

Why we recommend this:

The cutaway collar adds a modern touch, while the twill weave ensures durability and a bit of warmth for cooler seasons.

Image Credit: Mr. Porter

Essential Collared Dress Shirts: Formal

Note: This section explores the essential collar styles in detail, giving you the background needed to make thoughtful, informed decisions about your formal dress shirts.

Spread Collar

Medium Spread Collar

The medium spread collar is a classic choice that complements a wide variety of face shapes and tie knots. This collar style works seamlessly with traditional neckties and bow ties, offering a polished appearance when buttoned and an elegant yet approachable look when worn open.

Wide Spread Collar

The wide-spread collar is designed for a bolder and more distinguished look. With a greater distance between the collar points, this style is ideal for larger tie knots, such as the Windsor, and is perfect for men with longer or more angular face shapes. The wide-spread collar exudes confidence, making it a go-to choice for formal events and high-power business meetings.

Point Collar

The point collar is another classic option for its versatility and subtle elegance. Its collar points angled closer together create a more elongated appearance, making it especially flattering for rounder face shapes. The point collar is a staple in business dress shirts, offering a more traditional and understated look. It pairs well with slim ties and looks impeccable under structured suits, making it a must-have for professional attire.

Club Collar

The club collar, characterized by its rounded edges, adds a touch of vintage charm to any formal outfit. Originally popularized in the early 20th century, the club collar has made a stylish comeback in modern men’s fashion. This collar style works best with narrow ties and smaller tie knots (Four-in-Hand knot), and it can be enhanced with a collar pin for an extra dose of dapper flair. The club collar is ideal for those looking to add a unique element to their dress shirt collection.

Essential Cotton Dress Shirts for Men: Casual

4. Oxford Cloth Button-Down Dress Shirt

Cotton dress shirts are a foundational piece in any man’s wardrobe, thanks to their durability, breathability, and comfort. Among cotton dress shirts, the Oxford Cloth Button-Down (OCBD) stands out as an American classic. A light blue variation is a popular choice, as the Oxford fabric combines strands of white and blue, creating a subtle, textured color effect. The OCBD shirt’s versatility makes it a wardrobe staple, appropriate for both professional and casual settings.

The OCBD shirt can be worn with or without a suit, effortlessly adapting to various occasions, and its hard-wearing nature ensures it remains a reliable piece for years. Among button-down dress shirts, it stands out as a top pick for men’s casual dress shirts.

5. Flannel Dress Shirt

A flannel dress shirt provides warmth and style, making it an indispensable choice for cooler seasons. Known for its soft, brushed texture, flannel pairs effortlessly with casual outfits like denim jeans or corduroy trousers.

Flannel dress shirts are perfect for layering under a quilted jacket or a simple T-shirt. Classic patterns such as plaids or checks offer a rugged appeal, ideal for autumn outings and laid-back winter gatherings. As a classic long-sleeved dress shirt for men, flannel is practical and stylish.

Want to Master Flannel Style?

Get tips on pairing and layering your flannel shirts for the perfect casual look.

get the guide here

6. Soft Washed Denim Dress Shirt

Once considered unconventional, the soft-washed denim dress shirt has become a modern favorite. Its relaxed, casual vibe makes it perfect for toning down more formal outfits or adding a laid-back element to your wardrobe.

When to Wear a Denim Dress Shirt

While it may not suit a strict white-collar work environment, it’s ideal for off-duty days or smart-casual settings. Pair it with chinos or layer it under a blazer for a balanced, easygoing look. 

Despite initial skepticism about its staying power, the continued trend toward casualization in men’s fashion suggests that this shirt will remain a popular choice for years to come. 

EDITOR’S PICK FOR COTTON DRESS SHIRTS

BROOKS BROTHERS PORTUGUESE FLANNEL SHIRT

Why we recommend this:

Made from premium Portuguese cotton flannel, it provides a cozy feel with excellent durability, ideal for layering in cooler weather or wearing on its own for casual occasions.

Image Credit: Brooks Brothers

Essential Collared Dress Shirts for Men: Casual

Note: This section covers essential casual collar styles, offering insights to help you choose versatile, comfortable dress shirts for relaxed and semi-formal occasions.

Button-Down Collar

The button-down dress shirts originated from sportswear and have become a staple in casual and smart-casual wardrobes. It features small buttons at the collar points, keeping the collar neatly in place and giving the shirt a more relaxed and preppy appearance.

Ideal Pairings for a Button-Down Collar Shirt

Button-down collar shirts pair well with blazers and sports coats and can even be worn alone with chinos. While it’s less formal than a spread collar, it remains a classic option for men’s casual dress shirt selections.

Camp/Open Collar

The camp collar is a relaxed and modern option that adds charm to your casual wardrobe. Characterized by its open, flat-laying design, the camp collar eliminates the need for buttons at the collar points, giving it a laid-back appearance. This collar style is perfect for warm weather and casual settings, such as outdoor gatherings, vacations, or weekend outings.

Ideal Fabrics and Patterns for Camp Collar Shirts

Camp collar shirts are typically crafted from breathable fabrics like linen, lightweight cotton, or silk blends. They often feature bold patterns, vibrant colors, or understated prints, which is great for creating a statement but with a minimalist look. 

Styling Tips for Camp Collar Shirts

Pair a camp collar shirt with tailored shorts, chinos, or denim for a comfortable summer outfit. Layer it under a lightweight blazer or wear it open over a simple T-shirt for a more refined casual look.

Essential Patterned and Striped Dress Shirts

7. Striped Shirts

Blue Striped Shirt on White Background

The first striped dress shirt we recommend is a blue striped shirt on a white background—a classic choice for adding subtle patterns to your wardrobe. Patterned and striped dress shirts add variety to a collection, making them ideal for men looking beyond solid colors.

When choosing a blue striped shirt, opt for a stripe size that balances boldness and subtlety. Stripes that are too fine may look overly plain, while bold ones can limit your pairing options. A moderate stripe works well with a variety of solid suits, adding visual interest to your ensemble without overwhelming it.

Blue striped shirts pair effortlessly with solid and patterned ties, such as small Macclesfield neats or other subtle micropatterns. It’s a favorite among designer dress shirts for its elegance and versatility.

Fort Belvedere

Green Macclesfield Neats Tie

Pair this with your blue striped shirt!

Fort Belvedere

Light Blue Silk Knit Tie

Pair this with your blue striped shirt!

White Striped Shirt On A Light Blue Background

Select a stripe size that complements your existing wardrobe for a white striped shirt on a light blue background. A finer stripe is ideal, as it adds depth without overwhelming your outfit. From a distance, it will appear almost solid, providing a versatile look that pairs well with both patterned and solid ties.

The subtlety of the stripe ensures that even when layering patterns, like a striped tie, your overall look remains harmonious and well-balanced. It fits seamlessly into collections of modern dress shirts and stands out as a men’s white dress shirt staple.

8. Checked Dress Shirt

A checked dress shirt is another versatile addition to your wardrobe, available in classic patterns like light blue checks on a white background or red and blue checks on a white background.

Why a Checked Dress Shirt is a Must-Have

Both options add a touch of color and interest to your outfits, and red and blue remain timeless staples that integrate seamlessly into a classic wardrobe. They’re among the most popular choices for affordable dress shirts that don’t compromise on style.

Perfect for Casual Settings with a Button-Down Collar

To reiterate, a button-down collar is an excellent choice for more casual settings, as it complements the relaxed feel of a checked shirt. Button cuffs are also ideal for casual wear, enhancing the laid-back vibe while keeping the shirt comfortable and practical for everyday use.

EDITOR’S PICK FOR PATTERNED DRESS SHIRTS

ETON BLUE FINE STRIPED SHIRT

Why we recommend this:

The subtle stripe adds depth and elegance without dominating your look, making it versatile enough to pair with both solid and patterned ties.

Image Credit: Eton

Specialty Dress Shirts: Warm Weather Options

For warmer months, having dress shirts made from breathable fabrics like linen and seersucker is essential. These materials are designed to keep you cool and comfortable in high temperatures without sacrificing style.

9. Linen Dress Shirt

The first summer-friendly dress shirt we recommend is the linen dress shirt. The fabric’s lightweight and breathable nature ensures comfort in hot and humid conditions, while its natural texture adds a relaxed elegance.

Linens are best for warmer months!

Linen’s moisture-wicking properties make it ideal for summer events, from garden parties to coastal getaways.

Opt for neutral shades like white or beige for versatility, or experiment with pastel tones to add a splash of color to your casual wardrobe. You can find linen dress shirts at many retailers near you or have one tailored to your preferences.

10. Seersucker Dress Shirt

The seersucker dress shirt stands out for its distinctive puckered texture, which allows air to circulate and keeps you cool in high temperatures. This lightweight fabric is synonymous with summer style, providing a crisp yet casual appearance.

Seersucker shirts are typically seen in pastel stripes or classic blue and white combinations, pairing well with light-colored trousers or shorts. The shirt’s preppy charm makes it suitable for daytime social events, ensuring you remain comfortable and effortlessly stylish. 

Essential Dress Shirt Colors

Building a versatile wardrobe starts with choosing the right dress shirt colors. These foundational hues ensure your shirts are adaptable for various settings, from formal meetings to casual gatherings, making them indispensable in any well-rounded collection.

How a Dress Shirt Should Fit

Achieving the perfect fit for a dress shirt is essential for comfort and style. A well-fitted shirt enhances your appearance and ensures ease of movement. Key aspects to consider include:

• Collar: It should be snug yet comfortable, allowing enough room to insert two fingers between the collar and your neck.
• Shoulders: The shoulder seams should align precisely with the edge of your shoulders, ensuring a natural drape.
• Sleeves: They should end at the wrist bone, allowing about half an inch of cuff to show beyond a suit jacket.
• Chest and Waist: The shirt should fit close to the body without being tight, providing a clean silhouette without excess fabric.

For those requiring specialized sizing, many brands offer big and tall dress shirts to ensure a perfect fit without sacrificing style. Custom dress shirts are also an excellent investment, providing a personalized and precise fit.

For a comprehensive guide on achieving the ideal dress shirt fit, including detailed measurements and additional tips, check our in-depth article.

Outfit Rundown

I am wearing a classic white fancy weave shirt with a subtle waffle pattern. It features a shirt placket, French cuffs, a medium spread collar, and mother-of-pearl buttons. My cufflinks are gold monkey-fist cufflinks—timeless and versatile. If you’re investing in your first ten dress shirts, these would be the perfect cufflinks to pair with them because they work for almost any occasion. For a second pair, I’d recommend silver cufflinks, which are ideal for both formal evening events and less formal settings like board meetings or the office. They’re a purchase you won’t regret.

My jacket is green and part of a single-breasted suit, made from a slightly heavier fabric with beautiful color depth. I’ve paired it with a dark green madder silk tie, creating enough contrast, especially against the crisp white shirt. My pocket square ties everything together by picking up the green tones.

Fort Belvedere

Bottle Green Macclesfield Neats Madder Silk Tie

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Fort Belvedere

Brown & Green Large Paisley Silk Pocket Square

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Fort Belvedere

Mid Brown & Green Shadow Stripe Cotton Socks

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Fort Belvedere

Monkey Fist Knot Yellow Gold Vermeil Cufflinks

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The trousers, also part of the suit, are a brown and off-white houndstooth flannel. They contrast nicely with the texture of the jacket, and the warm, soft colors complement each other. My shoes are dark green suede tassel loafers, which echo both the brown tones of the trousers and the green of the jacket and tie, completing the look. I’m wearing brown and green shadow stripe socks that harmonize with the overall outfit, unifying the brown and green elements.

Do you have all these dress shirts in your closet? If not, what are your dress shirt essentials?

Fall is one of the best seasons for classic menswear because you can add additional layers in rich, subdued, earthy colors, which are just a joy to look at. It’s also the start of the season to wear winter accessories such as gloves, lightweight scarves, sweaters, vests, and all those things that just don’t make too much sense during the summer season.

As you prepare for fall, ensure your wardrobe is prepped with the fall essentials. To help you build an autumn wardrobe, we’ve compiled a list of must-have items, from head to toe, that every classic gentleman should consider adding this fall.

What Should You Wear for Fall? 11 (Plus 2 Bonus!) Must-Have Items for the Classic Gentleman

To embody the refined style of a classic gentleman, it’s essential to curate a fall wardrobe that balances sophistication with practicality. Below, we’ve outlined the top fall menswear essentials every elegant man should consider incorporating into his attire.

1. Unlined Gloves

When it is very cold, you naturally want the insulating benefits of cozy warm gloves. In transitional seasons like fall, however, unlined gloves have the benefit of a very refined and elegant appearance.

Also, during the transitioning season, you don’t need a cashmere lining or alpaca lining because it would simply be too warm. At the same time, going without gloves is a little bit too cold, so go with unlined gloves; it is the best of both worlds while giving you a chance to add some color to your outfit in an unusual way.

This classic style combination from the past proves that fall ensembles don’t have to be boring. It features unlined yellow gloves, a gray overcoat, and a flat cap, ideal for a refined gentleman’s wardrobe.

During the 19th century, when modern glove-wearing culture developed, the finest pair of gloves that a gentleman could own were chamois yellow, a bright and versatile color that could pair with anything.

Because he had a hard time finding unlined gloves, Raphael simply designed them himself as part of our Fort Belvedere line. He opted for a very lean, slim cut that is very elegant; he added a button at the wrist to ensure a tight fit. Raphael even created a line of driving gloves to wear with everyday outfits because they are airier and help to keep your hands cool.

If you go with unlined gloves, make sure to add a dash of color that is fall-appropriate because black gloves simply don’t suit the rich brown, green, orange, and whatever fall tones you incorporate in your wardrobe.

These unlined gloves are perfect if it’s not a too cold fall day but more of the warmer fall days. 

Fort Belvedere

Burgundy Suede Unlined Leather Gloves

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Fort Belvedere

Chamois Yellow Unlined Peccary Gloves

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Fort Belvedere

Navy Unlined Lamb Suede Gloves

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2. Knit Ties

Eaphael likes knit ties because they have this really nice texture, and today, you can find lots of knit ties on the market. Traditionally, the ones with the thickest texture are the cris de la soie ties, and they have the crunch in them; you can hear the crunch when you move it back and forth slightly. 

Traditionally, they were knitted flat then put on a wooden form and sewn together by hand, and that is exactly how we make our Fort Belvedere knit ties today. Most knit ties you can find on the market are knitted like a sock, and they are a lot more flimsy than the texture and the weft of the old-school quality knit ties. 

In terms of color, we suggest to leave behind the pastel colors and rather opt for something like bottle green, maybe a purple, or a bronze rust orange. Of course, you can also go with a tobacco brown, maybe a two-tone shade in cognac and dark charcoal, or a mustard yellow.

Because they have more texture, you can combine them with casual outfits such as a cardigan or a sweater, but you can also wear them with tweed coats, which are very elegant and stylish and very seasonally appropriate.

RECOMMENDED

Rust Orange Silk Knit Tie

Buy here

3. Suede Boots

Now, boots are, in general, ideal for fall because they are lined with leather most of the time, and they are not overly warm. At the same time, they keep you warmer than a regular pair of Oxfords or derby shoes. 

We suggest you get them with a thicker leather sole and use lace-ups. We personally think lace-ups are great with a suede shoe such as a chukka boot. Of course, you can also get different options, such as a desert boot in a sand color. We think the most versatile one that you can incorporate into your wardrobe is a mid-brown, maybe a chestnut brown, and the suede just gives it a softer character. 

If you can only afford one pair of boots, we suggest you go with something burgundy because you can combine it with a suit, as well as all kinds of casual garments. Also, if you want to spice up the look of your boots, you can simply go with contrasting colored bootlaces because that way, it looks like an entirely new boot, and you just invest a few dollars rather than buying an entirely new pair of boots. 

If you are not into lace-up boots, maybe you can consider a Chelsea boot, which is a classic with an insert, and to spice things up, you can maybe add a colored insert.

For more insights on essential autumn boots, check out our guide on essential autumn/fall boots. If you’re considering other stylish footwear options, our guide on loafers for fall and winter offers great alternatives. 

4. Vest/Waistcoat

The terms vest and waistcoat are used interchangeably, but no matter what you call it, it adds another layer to your outfit. Usually, it’s an odd vest, meaning it’s a contrasting color, and it just helps you to create entirely different looks into your existing wardrobe while keeping the budget very low. Vests in earthy hues like olive, brown, or tan can perfectly complement your fall palette.

5. Tweed Jacket/Sportcoat

If you follow the Gentleman’s Gazette regularly, you know that we love tweed. Raphael personally owns over a dozen of tweed jackets. The beauty of tweed is that it’s comprised of lots of different colors. From a distance, it might appear as a solid fabric, but up close, you’ll notice a rich blend of hues. Because of that, it is very easy for you to wear it with other colored garments, and it always looks like they work really well together. 

A darker to medium brown tweed coat pairs beautifully with fall trousers, adding a warm depth of color. This combination results in a harmonious, elegant, and seasonally appropriate look for fall.

How To Choose the right

Jacket for Fall

If you’re new to tweed, we suggest you get what is called a Donegal tweed which means there are little knobs all over the place in a contrasting color, or maybe with a simple oatmeal-colored herringbone tweed because it’s a very popular pattern, it’s very classic, and you can combine it with lots of things.

A traditional plaid tweed can also serve as an ideal top layer, providing both texture and a classic pattern to your outfit.

6. Quilted Jacket

A quilted jacket is great because it keeps you warm; at the same time, it is lightweight, and if you choose a length that covers your jacket, you can easily wear it on top without looking too formal. 

Also, you can wear it with casual outfits, and you can just put it on when you go to the gas station or get some groceries. It is also lighter than an overcoat and easier to travel with. If you like something that is a little more formal, we suggest you get a trench coat with a removable interlining because that way, you can wear it during the warmer days of fall in the beginning, as well as during the colder ones later on. 

7. Flat Cap

The flat cap is a staple of men’s fall fashion. It is a wonderful hat, providing both style and extra warmth. It is stylish and usually worn by younger men, even teenagers, as well as older men. The flat cap has seen a resurgence in popularity thanks to cultural influences, notably from celebrities like David Beckham and the TV drama Peaky Blinders, which have helped reframe it as a fashionable choice for all.

They are also not very expensive and are usually made out of tweed, making them easy to combine with other colors. It’s less formal than a fedora, making it a great entry-level hat that complements various hues in your wardrobe.

8. Wool Accessories

Most of the time, ties are made out of silk, and that is just fine; at the same time, maybe a pocket square in wool, or a tie, or a flat cap simply helps you to create a softer look in your outfit that is very appropriate for fall or autumn. Unlike silk, which is crispy and shiny, wool is softer and much more matte, which makes it very suitable for fall outfits.

Fall & Winter Silk-Wool Pocket Square

If there is just one wool item we think every man should have, it is a woolen pocket square simply because it helps to balance the texture even if you have an entire closet full of silk ties.

Moreover, it is less expensive than ties, so it is a great start if you don’t have any wool accessories yet.

Head out to our shop!

9. Corduroy Pants/Trousers

We know some people may think they make you look like an old professor in college or a school teacher, but corduroy is an ideal fall fabric and always has been because it is so warm and seasonally appropriate. 

Corduroy has a very nice color scheme, and because of the way the fabric is created, it has a different look in different light conditions, and it helps to create a soft overall outfit that is much better during fall-winter than it is during spring and summer. 

The great thing about corduroy is that it comes traditionally in lots of different colors, mostly earthy colors such as olive green, brown, and tan, which are very easy to combine during the fall-winter season.

Fort Belvedere

Goldenrod Yellow Stancliffe Corduroy Trousers

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Fort Belvedere

Dark Brown Stancliffe Corduroy Trousers

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10. Pastel Dress Shirt

Most men own white dress shirts, but to achieve a more harmonious fall look, consider pastel hues like eggshell, pale orange, pale pink, or light blue. These colors soften your overall appearance when worn under a tweed jacket or sports coat, avoiding the stark contrast that white can bring. A pastel shirt pairs effortlessly with classic corduroy trousers, blending perfectly with the subdued tones of men’s fall style.

11. Lightweight Knitted Sweaters

Usually, you don’t need the heavy woolen cashmere sweaters until later in the season, so you want a finer knit just to help keep you warm; at the same time, you want to look stylish. Because the knit is thinner, you want them close to your body, so it is a very flattering silhouette. 

Pairing a tie with a sweater is a stylish option. Just make sure you get a v-neck sweater because with a crew neck, it almost covers the entire tie knot, and it has a look that is not favorable. 

Avoid black and navy sweaters, as they tend to be too dark for fall. Likewise, stay clear of very light and bright sweaters because they are just too bright and don’t work with the rest of your fall wardrobe. 

Instead, go with a burgundy sweater, which is very versatile, or a medium blue, brown, oatmeal, bottle green, or maybe orange. All these tones harmonize beautifully with the fall season.

Two Bonus Essentials

Our next two items did not appear in our video, but we have added them as a bonus consideration for those of you reading our online content.

12. Flannel Shirt

Nothing embodies the coziness of fall quite like a flannel shirt. This cotton staple is great for achieving a rugged but polished look. Flannels often feature plaid patterns that bring texture and color into your wardrobe, aligning with the earthy hues of the season. 

Pair a flannel shirt with blue jeans for a laid-back weekend look, or layer it under a leather jacket for added warmth and style. To explore more ways to style flannel shirts, check out our guide on how to wear flannel shirts and our flannel guide for fall. 

13. Belts

A well-chosen belt is not just a functional accessory; it’s a critical component of a classic gentleman’s wardrobe that ties the whole look together.

For fall, consider belts made from rich leather in shades of brown, oxblood, or deep tan that complement the earthy tones of the season. When choosing a belt, ensure it matches or complements your shoes, especially if you’re opting for autumnal footwear like suede boots or leather brogues.

Don’t forget to introduce gold belt buckles to your ensemble, as they pair effortlessly with fall trousers and add a refined touch to your outfit.

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Jasper Gold Belt Buckle

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Classic Fall Outfits for Men

For a classic gentleman’s fall wardrobe, it’s best to avoid t-shirts and graphic tees, which can undermine the refined aesthetic of the season. Instead, focus on layering crisp dress shirts, lightweight knitted sweaters, and timeless outerwear like tweed jackets or quilted coats.

Using the classic fall pieces we listed, we’ve curated a fall look to inspire every gentleman. These outfits demonstrate how to effortlessly blend essential fall pieces for a polished and cohesive style that embodies the essence of classic menswear.

To replicate the exact looks showcased above, explore our fall lookbook, where you’ll find detailed guides on achieving each outfit.

Conclusion

As the leaves turn and the air chills, updating your accessory game is key to nailing the fall look. Whether it’s a classic wool pocket square that adds sophistication to any outfit, a leather belt that combines functionality with style, or a pair of boots that will crunch through the leaves, these essentials are more than just add-ons—they’re the subtle details that can elevate your entire ensemble. So, as you gear up for the season, remember that the right accessories don’t just complement your wardrobe; they complete it.

1. Trench Coat

During World War I, soldiers lived in awful environments and needed something they could wear for extended periods of time to help repel water, dirt, and general grime in the trenches. Makers like Burberry rose to the occasion and came up with a multipurpose military coat that soldiers could use for protection and general comfort while forced to live in these encampments.

It was so effective that the trench coat was what they literally lived, ate, and slept in, and it repelled the elements so well to the point that soldiers continued wearing it after the war.

Add in the fact that they were widely available in surplus stores after World War I, and their continued adoption by the broader public made the trench coat the iconic piece of outerwear we know it is today.

Hollywood only cemented its place in history by prominently featuring it in Casablanca when it was worn by World War I veteran Humphrey Bogart.

To this day, trench coats and many of the items we’re going to mention include features and accessories that haven’t quite left the battlefield behind. Once, Raphael was wearing his trench coat in the GG office and Teresa asked him, “What are those rings for?” Raphael nonchalantly replied, “For holding grenades.” In fact, there’s a disagreement about whether trench coat D-rings were used for this purpose. But, it’s still a great story.

2. Pea Coat

Originally popular in the British Navy after being adopted from the Dutch, mainly because they were extremely warm and easy to move around in when compared to the knee or ankle-length great coats seen in other branches of the military. In fact, petty officers were expected to climb up ropes and swab decks while wearing them. We wouldn’t recommend trying that yourself, though. 

Given that the coat had a great combination of practicality and stylish features, pea coats soon gained traction with offerings at military surplus stores and became beloved by civilians who appreciated their overcoat-like style while being just short enough to be worn more casually, leading to it becoming the business casual staple piece of outerwear it’s known as today.

3. Field Jackets

Field jackets had uses in World War I and World War II and had a popular offshoot with the older models more resembling the safari bush jacket as we know them today. Although, despite having crossover with military styles, the safari jacket is better known today for being used in hunting excursions and recreational trips.

Still, the iconic M65 model field jacket is what gained popularity in the Korean and Vietnam conflicts and allowed the jacket to truly become its own thing. The M65 was an extremely practical garment that had excess pockets and built-in features like a hood and was designed to be like a modern version of the trench coat during the winter months of military campaigns, where soldiers lived in these jackets and continued wearing them even after they returned from war.

The jacket was even worn ironically by protesters and icons of the counterculture revolution like John Lennon and Bob Dylan as a way to show opposition to the Vietnam conflict, making regular citizens later adopt them more as a fashion statement than their original use.

Nowadays, the jacket style and material will vary from its original rugged and coarse exterior to extremely refined. Even makers like Loro Piana make high-end versions of this jacket now, like the Windmate Traveler model, which works surprisingly well when combined with elements of fine tailoring.

4. Aviator/Bomber Jackets

Leather jackets were favored by pilots in World War I and World War II, with the B3 model being one of the most iconic. Before enclosed cockpits were invented, it was extremely cold while flying in the open air, making the experience a literal ice box and, even after enclosure, they didn’t have climate control and it gets chilly at 25,000 ft.

The Aviator’s Favorite

B3 Jacket

American pilots began to favor the B3 leather jacket made with shearling, which helped to provide enough warmth and insulation to the wearer without losing any critical range of motion. Even as cockpits improved, it became popular for pilots to have their own signature leather jacket for tradition’s sake. Look no further than Top Gun to see that idea in action.

Given the prestige and cool factor that comes from being a fighter jet pilot, civilians soon wanted to mimic these styles and the jacket evolved into what we know as the bomber style today.

For more on bomber and flight jackets, we’ve got you covered with a separate guide.

5. Chinos

Chino cloth is a twill fabric woven from cotton and was intended to be breathable hard-wearing fabric for the British military when running campaigns in Africa, India, or other desert or tropical environments. The iconic khaki color serves as a type of early camouflage as if someone blended in the sand dunes or other dusty landscapes.

They’re so associated with the British army that Boers refered to British soldiers as “die Kakies.”

Chino fabric was adopted into other military offshoots, such as Gurkha trousers, after being adopted by the feared Gurkha soldiers of the Indian subcontinent.

Outfit Rundown

Today, I am wearing a linen shirt as it’s extremely hot outside. It is in a light blue color, and then, as I mentioned before, I am wearing a pair of khakis and I am wearing a pair of white sneakers from Common Projects. For accessories, I am wearing my Seiko 5 watch with a steel band. I’m also wearing two silver necklaces.

To harmonize with the blue on my shirt, my fragrance today is Blue Suede Shoes from Roberto Ugolini. For this fragrance and others for the Roberto Ugolini collection, as well as classic menswear accessories, check out our Fort Belvedere shop here. 

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6. T-Shirts

The military made wearing a T-shirt as an outer garment a thing. We first started seeing T-shirts being adopted as a part of military uniform in World War I by the US Navy, and other branches followed suit.

T-shirts were explicitly undergarments, required to be worn under uniform shirts. However, going into the 1930s and 1940s, uniform requirements were relaxed, and soldiers were allowed to wear their T-shirts around camp and base under certain circumstances. Some soldiers continued the practice once they returned home and would even add graphics to the front of them to help distinguish them as an intentional outerwear choice.

Their rough and tumble association fit perfectly with Marlon Brando’s character in A Streetcar Named Desire, and the T-shirt soon became a symbol of rebellion and non-conformity, eventually leading to one standard-issue uniform becoming the current super casual default style for many civilians.

7. Blucher Shoe

Next, let’s turn to footwear. You may have heard of a type of shoe similar to a derby called a Blucher with a one-cut vamp made from a single piece of leather. Turns out, the name was a reference to Napoleonic-era Prussian Field Marshal Gebhard von Blücher, who commissioned the shoe to assist his soldiers when marching for long periods in the field.

The open lace system meant the leather did not have to be worn so tightly around the ankle and allowed for a more comfortable and functional experience in general. Soon, the other European nations began to copy the innovation and the lacing system around the vamp is still seen as the preferred method of use for casual and business casual shoes.

8. Wellington Boots

Let’s keep marching with footwear.

The Wellington’s Royal Origins

The Wellington boot started out as a variation on the older Hessian boot and was first introduced by the Duke of Wellington Arthur Wellesley, who wanted a practical and water-resistant boot for his soldiers. The style was later adopted by farmers and other English workers who needed to trudge around in muddy environments.

It was also popularized by the Hero of Waterloo as a fashionable civilian guard, without which Billy Connolly would be in hospital or infirmary, and soon was even imported and assimilated in the US, contributing to the refinement of the cowboy boot.

To this day, Wellingtons remain a popular rain boot, lovingly called “Wellies,” and we’ve done an article on them as well. 

9. Desert Boots

Meanwhile, the desert boot was a variation of the athletic chukka boot, which was adopted from the Indian subcontinent into footwear associated with the sport of polo. It allowed for mobility while still helping keep dirt away from getting underneath your pants.

Unique desert boot varieties similar to chukka boots were worn by various armies throughout the early 20th century, meaning that the chukka was effectively reborn on the battlefield as the desert boot. Technically speaking, though, no definitive desert boot existed until 1949 when the C&J Clark Shoe Company in Great Britain standardized their take on the desert boot as a crepe-soled chukka with a suede upper.

The desert boot enjoyed popularity as a hardwearing but comfortable civilian boot, and advertising often played off of its military heritage. 

10. Aviator Sunglasses

Next up, we’ve got an accessory. While goggles that protect the eyes from glare have been around for millennia, aviator sunglasses are uniquely military. This particular design was intended expressly for military functionality with their large and convex frames designed to block the sun from all possible angles—since one bad attack of glare could be the difference between life or death in a dogfight.

Soon, Hollywood actors during the Golden Age of Menswear began wearing sunglasses, and many prominent actors from the time served in at least one of the World Wars as well, which led to other people mimicking the style themselves while outside.

The aviator arguably hit its peak popularity during the 1980s, when Top Gun prominently featured them as something every pilot wore and could help them see the highway to the danger zone.

11. Mess Jacket

Believe it or not, even some of these pieces of formal wear have military origins. Mess jackets were first introduced as formal uniforms in prestigious English schools like Eton around 1800; and by the mid-19th century, they had carried over to the military, where they were less fussy and more utilitarian than tail coats. Not to mention, considerably cooler. We mean literally cooler, although, they look cool, too.

Mess jackets were soon adopted by more militaries around the world as formal attire and broke into the civilian world in 1931 as one of the biggest and earliest fads of the Golden Age of Menswear. In fact, the mess jacket became a victim of its own popularity as the owners of nightclubs and restaurants began to dress their staff like waiters or bellhops in it to appear trendy, so that by 1934, the trend fizzled as men feared being mistaken for the help. 

12. Cummerbund

Mess jackets haven’t quite survived outside of military settings, but our final item certainly has. The modern cummerbund is modeled after the waist sashes, which were originally worn by British military officers who served in more hot and humid climates like India.

The traditional waistcoat—that was ubiquitous at the time—covered more of the body, which could cause the wearer to become overheated. Instead, soldiers opted to borrow from the sartorial customs of the places they served, and they used these sashes as a way to still have a proper waist covering since leaving the shirt front around the waist exposed was the equivalent of walking around in your underwear.

Eventually, the literal sash was replaced with the cummerbund we know today, the pleats of which are intentionally evocative of the folds of a sash. This style caught the interest of the royal courts and the public once these soldiers returned home with this new-found style and, now, the cummerbund has replaced the evening waistcoat as a preferred Black Tie evening waist covering. Classic menswear and military attire developed together, so it’s no surprise that these items made their way from the battlefield into stylish gents’ wardrobes.

To learn more about how military fashion broadly impacted classic style, check out Preston’s guide on the military as the secret source of classic menswear.

What’s your favorite military-turned-menswear item story? Let us know in the comments.

Warm-Weather Looks for Various Settings

Today, we’re highlighting 15 individual outfits that we feel are suited to particular occasions and events. These ensembles are intended to inspire your own looks. We certainly don’t expect you to copy them exactly or wear these types of outfits only at the particular type of event that we are identifying. Again, we’re just sharing examples.

We’ll also be mentioning existing content that more fully explains the concepts behind these ensembles. So, be sure to peruse those links if you prefer fuller explanations of why we feel these outfits are so well-suited to warm weather occasions. However, today we’re going with a show-don’t-tell approach, so let’s get showing!

Picnics, Barbeques, and Similar Private Outdoor Events

For our first collection of outfits, let’s consider private outdoor events, including eating events like picnics or barbecues or gatherings with activities like lawn games. For such occasions, you want simple, comfortable outfits that will allow you to have fun, not worry too much about keeping your clothes neat, but still present a nice figure whether you’re hosting or a guest. Even if it’s just a cookout, you don’t want to look like a slob.

Outfit #1

In our first suggestion, Raphael is wearing a light gray polo shirt with stone chinos and light cognac fisherman sandals. This ensemble emphasizes coolness, which is a necessity when outdoors in the heat. The sleeves are short. Raphael is not wearing any neckwear. His trousers are cut fuller to allow easier air circulation, keeping air moving freely over your skin. It’s one of the easiest ways to keep cool, as Preston explains in our guide on “Beating the Heat in Style.”

While very cool, most of this outfit is very neutral and unassuming, so the unique sandals are a great way to add personality. I’m just glad that Raphael didn’t pair them with socks; a trait all too common among our Teutonic friends. Keeping your feet cool is critical to keeping your body cool as we discussed in our guide to summer shoes.

Outfit #2

For an outfit that is similarly refreshing but with a bit more personality, here’s Raphael in a dapper yellow polo with light blue denim chinos, a casual jacket, and orange-red boat shoes. 

Even though nearly all of the elements of this ensemble are casual, the pleasing way that the colors harmonize elevates the entire look without sacrificing its cooling potential. In this content, you’ll learn how to employ warm and hot weather colors.

Outfit #3

Short sleeves are fine for tossing the hacky sack or batting a pickleball, but what if you’re enjoying hot dogs and hamburgers with some new neighbors and want to make a slightly more formal impression?

A collar and long sleeves go a surprisingly long way. Here, I’m wearing a gray and white striped shirt with a button-down collar, paired with denim for some stretch and breathability, and brown suede chukka boots. I rolled up my sleeves to keep the air circulating so I won’t overheat.

The structured appearance of the collar and longer sleeves, plus the sedate colors of the ensemble, add a slight air of formality that isn’t stuffy or uptight but is perfect for lounging around the fire pit. For casual private social events outdoors, your main concern is keeping cool, but you don’t have to sacrifice classic style to do so.

Outings in Public

Let’s stick with the outdoor element, but shift things publicly, such as walking the dog, strolling around your neighborhood, or visiting the park.

Keep cool with

Short-Sleeved Shirts & Polos

Once again, you’re going to be out in the hot elements, and you may not have convenient access to a patio or a deck with fans, so keeping cool is critical. Also, you’re not necessarily planning on meeting anyone. So, you can be more casual. But, because you’re also out in public, you don’t know whom you may encounter, so you want to look as well put together as possible.

Polo shirts are your friend. They have the same cooling Factor as T-shirts, but that simple addition of a collar is just so much more presentable. You can find your next perfect polo with our polo shirt guide. I’m wearing one of my favorites in my next outfit.

Polo Shirts: Your Guide to Buying, Styling, History & More

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Outfit #1

It’s a cream Ralph Lauren polo that I paired with dark blue shorts and brown Minnetonka Moccasins. Find out if we think they’re worth it in our review. The shorts and mocs make it obvious that I’m dressing for comfort, but the upscale effect of the cream and blue pairing is very dapper. Plus, the presence of leather shoes and a collared shirt means that I won’t be embarrassed if I run into someone I know. Shorts are criminally underutilized in classic style, but we show you how to integrate them into your wardrobe with our comprehensive guide.

Outfit #2

If shorts aren’t your thing, you can enjoy similar cooling with long trousers. These are generally cut looser, like the Gurkha trousers paired here with a red polo and ox blood derbies. In addition to their loose drape, Gurkhas are so comfortable because they’re made from breathable materials with a more open weave like cotton; wearing fabrics proper to warm and hot weather is critical, as Raphael covers in our guide to summer fabrics.

Of course, another benefit of wearing trousers is adding a pair of over-the-calf socks to your ensemble for an additional element of color and style—just like the ones I’m wearing today, which are a blue and red shadow stripe.

I’m putting that together with a pair of navy trousers, blue suede boots, a blue-based blazer with different shades of blue, and a light blue dress shirt with a mandarin collar; and, of course, finishing off the outfit with a white pocket square from Fort Belvedere today.

I’m also wearing the Marzocco from Roberto Ugolini. For other Roberto Ugolini fragrances, corduroy trousers, and other classic menswear accessories. Check them out at the Fort Belvedere shop.

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Outfit #3

Keeping the sunlight off your skin is critical to staying cool. Here, Preston is wearing a blue and white sport shirt with beige trousers, suede loafers, and his much loved hat. That hat is not only keeping the sun out of his eyes, it’s preventing its rays from hitting his skin and warming up his face.

In our guide on summer hats, you’ll learn more about the ways that these handy accessories keep you cool, but in general, remember that whenever you’re taking the air around your neighborhood, prioritize comfort but don’t forget you are in public.

Errands

Necessary tasks like running to the grocery store or pharmacy are rarely fun, but when it’s also hot outside, they can really feel like a chore. Don’t let that be your excuse to look like a bum when you head to the market, though, as you never know the impression you might give.

Outfit #1

In this ensemble, Preston combined most of the points that we’ve covered already, employing a short sleeved polo in a conservative navy with brown, loose-cut trousers and comfortable shoes.

With his trusty hat, his colorways say “shopping dignity” and his heat-beating techniques avoid “shopping sweaty.” You’ll also notice his glasses— shaded eyeglasses or sunglasses are an essential accessory that warrants their own explanation for both functionality and fashion appeal. 

Outfit #2

Our videographer, Chris, cuts a very similar figure in our next ensemble, where you’ll notice he’s wearing a long-sleeved polo.

keep sun away With

Long Sleeves

You might think that he’d overheat in this garment; but when the fabric is breathable, longer sleeves can actually be better than shorter because, just like a hat, the sleeves can keep the sun’s rays off your skin, preventing that transfer of heat.

We hope that these examples prove that even when running errands, you can still be functional and refined.

Daytime Meals

Let’s turn back to the social from the practical by considering ensembles to wear when going out to eat in the heat. In these circumstances, you’re meeting others, you’re going out in public or dining in, so you assume a certain obligation to look nice, even if it is hot outside.

For these examples, we’re assuming that you’re having lunch at a residence or restaurant with no dress code; if there is a dress code, naturally, follow it.

Outfit #1

For our first look, let’s keep it basic. We’ll employ breathable fabrics and seasonal light colors. These will maximize airflow. Here, Chris is wearing high-rise chinos with a tasteful yellow polo, horse-bit loafers, and a flat cap. All these elements are relatively casual and very cooling, but because of tasteful details like the elegant, yellow shade of the polo, wearing a collared shirt, having on leather shoes, and sporting a classic cap, Chris looks better dressed for lunch than most people for a formal dinner.

Outfit #2

For a look with even more personality, let’s turn to David. Here, he pairs a blue and white striped shirt with white trousers, suede loafers, and a bold safari jacket. This look is distinctive and memorable. Thanks to its neutral palette, it isn’t disruptive or distracting. It’s also quite cool, but you may be asking, how can that be with a jacket?

When you are wearing multiple layers, if all those layers are made from natural, breathable materials, the negative impact that each has on air flow will be minimal. That’s one of the reasons why one of our writers, Eb, has no qualms with wearing an undershirt—both in his native Atlanta, Georgia and when visiting Venice, Italy.

The fact of the matter is, just like a collar elevates a shirt, a jacket elevates any ensemble. So, for any hot weather lunch where you really want to look your best, we strongly recommend that you consider wearing a jacket. You can always take it off if necessary.

Outfit #4

Here, Ivan showcases a look that really puts the fresh in al fresco. He has on a light blue shirt, light gray sport coat, white trousers, and horsebit loafers; you’ll notice that he isn’t wearing a tie to reduce insulating and heat-inducing bulk at his neck, but he does have a pocket square to create comparable visual interest in the area.

For those occasions when you need to dress to impress with the most formal iterations of casual attire, there’s no reason that the heat should stand in your way.

Evening Meals

To conclude here, let’s consider what is likely to be the most formal of casual, warm weather occasions—whether enjoyed in a private abode or a public venue, evening meals are usually the most refined and dignified.

So, you want to dress the part to impress your hosts or guests and anyone else who might be present. But, of course, you also don’t want to be dying of heat exhaustion.

Outfit #1

First, let’s consider a combinational ensemble; it’s broken up principal elements typically appear much less formal than a suit but are still elegant. Here, Preston is wearing a white shirt and trousers, a color choice sure to keep him cool with a reddish brown, light wool, sport coat; suede loafers; and light, bright accessories, including a boutonniere and pocket square.

The diametric color choices of brown and white keep the ensemble simple and grounded, but still sufficiently put together for dinner. But, notice once again, just how casual this ensemble looks without a tie.

Outfit #2

If you prefer neckwear, even with your more casual looks, bow ties are ideal for hot weather as they reduce the excess fabric that traps heat. Here, we show the casual cool of a combinational look—contrasting a sport coat with light trousers with a versatile, light blue shirt and a fun orange tie with red polka dots.

While clearly dressed up, the fun and youthful components of this ensemble, expressed by its preppy demeanor, prevent it from being too stuffy or straying outside of business casual.

Outfit #3

For our last look, let’s prove that you can wear a suit as part of a warm weather casual look. Here, Ivan is wearing a brown suit. He also has on dark oxblood loafers with a simple white shirt and white pocket square with contrast stitching.

While the suit color is typical of a day ensemble, it’s dark enough for a casual evening affair. The white shirt and pocket square keep things simple, as do the darker shoes, but the fact that he’s in a suit, even one without a tie, indicates an intentionality when dressing and the desire to make every day a special occasion—typical of someone who always dresses well, a subject that Raphael discusses in a separate guide.

Conclusion

With that, we’ve covered warm weather occasions—from running errands to al fresco dining—and ensembles ranging from shorts and a polo to a suit. As you’ve seen for yourself, hot weather needn’t prevent you from dressing well, even for the most casual events.

Let us know in the comments how you dress casually when the thermometer is rising.

Resort Attire, as you might expect, refers to the unofficial dress code of clothing that typifies resorts, be they in vacation destinations or just the ritzy parts of town. Unlike conventional dress codes, men’s resort wear entails a very wide range of formalities, and what you wear when will be very dependent upon precise circumstances. 

In this guide, we will define exactly what Resort Wear is, where you will be expected to employ it, the elements that constitute it, and how you can prepare a stylish ensemble that will make you the talk of the town. 

What Resort Attire Is

Why It Exists

Resort wear is a dress code that ensures a certain standard of attire for guests. It suggests a dress code that balances formality with the relaxed atmosphere of a vacation setting in a warmer climate. It fundamentally consists of smart, well-put-together clothing that respects the upscale ambiance of a resort while acknowledging the tropical or seaside environment. 

This dress code suggests a smart, casual look that’s comfortable yet polished, suitable for most activities at a resort such as dining, socializing, or exploring. But while guests are encouraged to dress nicely, traditional business or evening wear such as dark suits or tuxedos would be excessively formal and out of place. Instead, lighter fabrics, cheerful colors, and a more casual yet sophisticated style of dressing are appropriate for resort settings.

Balancing Formality

The term Resort Attire can be somewhat nebulous, as interpretations of resort wear may vary from one establishment to another. However, it is prudent to consider the level of luxury and formality inherent to the venue when selecting appropriate attire.

Generally, the more prestigious and opulent the setting, the higher the expectation for formal dressing will be. Consequently, guests should opt for more elegant and sophisticated clothing options to align with the elevated sartorial standards these establishments uphold, rather than casual or beach-appropriate garments such as board shorts that could be suitable in other areas of the resort like the beachfront or spa.

Where You Wear It

Resort attire is a versatile clothing style designed for the sophisticated traveler and is typically expected at upscale resorts, especially in tropical destinations. You’ll find resort attire appropriate for specialty restaurants, country club meetings, and even on some cruise lines during the daytime; accordingly, Resort Attire is sometimes called “Cruise Wear.” It strikes a balance between relaxed and refined, making it perfect for vacationers who want to look well-dressed without sacrificing comfort.

When packing for a destination that suggests resort attire, think of places like beachside bars, poolside cabanas, or yacht clubs where the atmosphere is laid-back but still maintains an air of elegance. Additionally, many warm-weather wedding receptions or outdoor corporate events may request resort attire to ensure guests are appropriately dressed for both the occasion and the climate. The key is to aim for clothing that is both functional for the setting—lightweight fabrics for warm weather, for instance—and stylish enough to reflect the upscale environment of the resort or event.

What Resort Attire Isn’t

Avoid These Common Resort Attire Mistakes!

1

Don't wear athletic attire

Outside of a gym or when exercising, athletic attire is too casual and inappropriate for Resort Attire. This includes, but is not limited to, gym shorts, t-shirts, track pants, sweatpants, joggers, and workout shorts. It is advisable to refrain from wearing t-shirts or tank tops; instead, opt for shirts that feature a collar, such as polo shirts—either with short or long sleeves— sport shirts, or light-colored dress shirts.

2

Establish the dress code for other casual clothing

The acceptability of attire such as golf khakis, shorts, or slacks paired with a polo shirt can vary by establishment. Therefore, it is beneficial to inquire about or ascertain the specific dress code of the venue in question.

3

Avoid very casual footwear

Footwear should also reflect the elevated ethos of Resort Attire; thus, the wearing of shower slides, flip-flops, or sandals should be confined to the beach or poolside locations. Athletic footwear, including tennis shoes or trainers, should be avoided. When selecting sneakers, it is prudent to opt for leather dress sneakers. Conventional leather dress shoes in hues like tan, or perhaps suede options in green or dark brown, are recommended. Black shoes, although classic, may convey an excessive level of formality for most Resort Attire occasions.

4

Don't be overdressed

Certain more formal or refined clothing elements may appear over-the-top in a resort setting. Cufflinks, plush neckties, formal shoes, and similar details may be acceptable in the evening but could seem stodgy during the day. Also, as a practical measure, avoid excessive layers, such as vests, waistcoats, and topcoats in most situations as they can be stifling and hot.

Daytime Resort Attire Garments

Keep It Casual and Cool

During the daytime, you will hopefully be spending most of your time eating al fresco, lounging by the pool, chatting with friends, or getting in a game of golf. Accordingly, expect daytime ensembles to lean more into casual styling, with an emphasis on staying cool and comfortable.

Shirts

Because you may or may not be wearing a jacket, your shirt is likely to become the centerpiece of your ensemble. Therefore, it is especially important that you select a vibrant but elegant option that adds personality while accounting for the realities of the hotter temperatures typical of resort and vacation areas. 

Linen Shirts

A staple of resort wear, linen shirts offer a breathable fabric that is ideal for warm climates. Their lightweight nature allows for air circulation, keeping the wearer cool. Linen shirts typically come in long and short sleeve variants, with a preference for pastel shades or white, which reflect sunlight and enhance the shirt’s cooling properties.

Polo Shirts

For a sportier look that still fits within the resort attire category, polo shirts are a great option. They are versatile and can be dressed up or down depending on the occasion. Polos made from performance materials offer additional comfort and moisture-wicking properties, which are beneficial in hot and humid environments.

Popover Shirts

Popover shirts are essentially a hybrid between a polo and a traditional button-up shirt. They typically have a four-button placket and can be found in various fabrics, including linen and lightweight cotton. This style offers a more structured look while maintaining the ease of a pullover garment. When curating shirts for a resort wardrobe, the key is to focus on breathable fabrics, comfortable fits, and a clean, well-groomed appearance. Patterns and colors can vary, but they should always maintain a certain level of refinement to adhere to the upscale nature of resort settings.

Should you wear

Neckwear?

Especially today, most types of neckwear are considered too formal for daytime resort settings unless you happen to be eating lunch in a more upscale restaurant. That being said, a sufficiently casual accessory, like a playful bow tie or a silk knit tie, can be worn if desired; opt for bright, fun colors and patterns.

Casual Silk Shirts

Silk shirts are the epitome of luxury within the resort attire spectrum, offering a sleek and smooth texture that drapes elegantly on the body. These shirts are inherently dressy due to the sheen and feel of the fabric but can be styled casually to fit the resort casual dress code, especially when they feature colorful prints. When selecting a silk shirt for a resort setting, opt for those with muted tones or subtle patterns to maintain an air of sophistication. While silk is less breathable than cotton or linen, it compensates with its lightweight nature and soft touch, making it suitable for evening events or cooler days. It’s important to note that silk requires careful maintenance to keep it looking its best, but its luxurious appeal makes it worth the effort for many resort-goers.

Aloha Shirts

Also known as Hawaiian shirts, Aloha shirts are recognized for their bold tropical prints and bright colors. While they are casual, selecting an Aloha shirt with a subdued pattern can align with the resort chic dress code. These shirts are traditionally made from silk or cotton and are designed to be worn untucked, offering a relaxed fit.

Trousers

Trousers are a fundamental component of the Resort Attire dress code, offering a blend of sophistication and relaxation suitable for upscale vacation environments. The right pair complements the breezy shirts typical of resort fashion, ensuring both comfort and style.

When curating trousers for a resort wardrobe, prioritize materials that offer breathability and movement. Especially during the day, stick to lighter shades to reflect the sun’s rays. The goal is to achieve a look that’s effortlessly chic, comfortable for all-day wear, and adaptable to the various activities that a resort setting offers.

Linen Trousers

A favorite for their breathability and lightness, linen trousers are synonymous with resort wear. They come in various styles, from straight-cut to more relaxed fits, and are available in an array of neutral and soft pastel colors that reflect the serene resort setting.

Chino Pants

Chinos are a versatile option that can be dressed up or down depending on the occasion. Made from a lightweight cotton blend, they provide comfort without compromising on style. For a classic resort look, choose chinos in beige, navy, or light gray.

Classic Shorts

When temperatures rise, classic shorts become an acceptable and stylish choice within the resort attire category. Aim for a mid-thigh to knee-length cut to maintain a polished appearance. Pair them with a lightweight button-up shirt or polo to keep the look refined.

What about

Madras shorts?

Madras shorts are a vibrant and playful addition to the Resort Attire wardrobe, injecting a dash of color and pattern into the ensemble. Originating from the Madras region in India, this lightweight cotton fabric is known for its plaid patterns in various bright and pastel hues.

White or Light-Colored Jeans

A crisp pair of white jeans can also fit into the resort attire dress code, especially for cooler evenings. Opt for a slim-fit or straight-leg cut in a lightweight denim to ensure comfort and style.

Seersucker Pants

Seersucker fabric, known for its puckered texture, is another excellent choice for resort wear due to its heat-dissipating properties. Seersucker pants in classic stripes offer a preppy vibe that’s perfect for seaside resorts.

Shoes

Footwear is a critical aspect of the Resort Attire dress code, as it can define the overall tone of the outfit. The right shoes not only complement the look but also provide comfort for all-day wear in a resort setting.

When choosing shoes for resort attire, consider the activities you’ll be participating in and the level of formality of the venues you’ll be visiting. Always aim for a balance between elegance and practicality, ensuring your footwear choices enhance your overall resort experience while keeping you comfortable and stylish.

Loafers

Loafers are a classic choice that offers both comfort and style. Leather or suede loafers in neutral colors like brown, navy, or tan can easily be dressed up or down. For a more nautical feel, opt for a pair of boat shoes, which are specifically designed for seaside wear.

Driving Mocs

Driving moccasins, or driving mocs, are another excellent footwear choice for the discerning resort-goer. These slip-on shoes are designed with comfort in mind, featuring soft leather and a flexible sole. Their sleek design and practicality make them ideal for navigating the resort in style, whether you’re lounging or taking a leisurely drive. Available in a variety of colors and finishes, driving mocs can easily complement your resort attire, adding a touch of laid-back luxury to your look.

Boat Shoes

Also known as deck shoes, boat shoes are a timeless and functional choice for resort wear. They are characterized by their non-marking rubber soles with siping (thin slits) for traction, leather construction that can withstand saltwater, and lacing system along the sides for a snug fit. Boat shoes are typically worn without socks and pair well with shorts, chinos, or linen trousers, making them versatile for various resort activities from boating to dining al fresco. Their classic design, often featuring shades of brown, navy, or tan, provides a relaxed yet preppy look that is perfect for the laid-back elegance required in resort settings.

Leather Sandals

A pair of high-quality leather sandals is essential for resort wear. They should have a refined look, with clean lines and minimal embellishments. Choose a style that secures the foot well and provides support for walking long distances, whether you’re exploring the resort or heading to the beach.

Espadrilles

Espadrilles are the quintessential summer shoe, featuring a canvas or cotton fabric upper and a flexible sole made of esparto rope. They are lightweight and come in various styles, from slip-ons to those with ties that wrap around the ankle, adding a casual yet chic touch to any resort outfit.

Accessories

Accessories play a pivotal role in elevating and personalizing the Resort Attire look. They should be chosen with care to complement the outfit without overwhelming it. When accessorizing for resort wear, the key is to think understated and functional. Accessories should enhance your comfort and convenience while reflecting the leisurely spirit of your surroundings. Remember, the best accessories are those that blend seamlessly with your outfit, providing an effortless finish to your resort look. 

Socks

Resort Attire is one of the few Classic Style dress codes that allow you to go sockless, but your feet will thank you if you instead opt to wear no-show socks. They offer the same clean, casual appearance of eschewing socks but with reduced chafing and stickiness.

Watches

A watch is a subtle accessory that can make a statement about your style. For resort wear, opt for timepieces with a nautical or casual flair, such as those with a canvas or leather strap. If you’re planning on water activities, a waterproof watch is a must.

Sunglasses

A stylish pair of sunglasses is indispensable for any resort getaway. Not only do they protect your eyes from the sun, but they also add a touch of sophistication to your appearance. Classic shapes like aviators, wayfarers, or clubmasters are versatile options that suit most face shapes.

Belts

A belt can serve as a functional accessory to ensure a proper fit of your trousers or shorts, as well as a decorative piece. Choose a woven or braided belt for a relaxed look, or a classic leather belt for a more refined touch. The color of the belt should coordinate with your shoes for a cohesive look.

Scarves & Day Ascots

For a bit of flair, you could incorporate a lightweight scarf or foulard made of linen or cotton. For a dapper vintage appearance, consider a day ascot, also called a casual cravat. Choose one with a subtle pattern or in a solid color that completes your outfit.

Hats

To shield yourself from the sun while adding a fashionable element to your outfit, consider a Panama hat, a cotton or linen flat cap, or a fedora made from lightweight straw. These hats are both functional and stylish, perfect for a day spent outdoors.

Evening Resort Attire Garments

Formal Can Still Be Fun!

In general, evenings at resorts are more elevated and formal than the daytime. You will likely be enjoying fresh fare in a fine dining establishment, relaxing barside, or racking in your winnings at the casino. Accordingly, expect to incorporate more formal detailing into your outfits, including the addition of a jacket and more elevated accessories.

Jackets

As the sun sets, the question of whether to don a jacket as part of your resort attire arises. A well-tailored blazer can elevate your outfit, providing an extra layer of style for dinner or a night out. Opt for materials like lightweight cotton, linen, or a breathable wool blend that offers comfort without overheating. For those balmy nights, a light sports coat or an unstructured jacket can add a touch of formality while keeping things casual. However, always consider the event’s dress code and location; a jacket may not be necessary for more laid-back venues or tropical settings. The key is to ensure that your jacket complements your trousers and enhances your overall look without compromising on comfort.

Shirts

As a general rule, evening Resort Attire shirts should mostly be long-sleeve sport shirts or dress shirts, although if you prefer a more laid-back look, short sleeves are acceptable, provided they follow all stated dress codes. For the greatest versatility, opt for dress shirts made from cotton, linen, or silk in bold but elegant bright colors like pastels or with subtle patterns. A more open weave will help keep you cool even if the night turns sultry. 

Should I wear

Neckwear?

In most cases, a tie will always elevate your Resort Attire look, especially in more formal settings like a restaurant or casino. To match the whimsy of the location, consider fun and unique options, like silk grenadine, a knit, or anything with texture or a fun pattern.

Resort Attire Ready Neckwear from Fort Belvedere

Breezy and Elegant

Knit Tie in Solid Yellow Pale Silk

Let the Sunshine In!

The Flower of Summer

Orange Red Jacquard Bow Tie

Wear the Island Sunset!

Cool and Refreshing

Grenadine Silk Tie in Dark Blue

Ride the Wave!

Trousers

When it comes to resort attire for the evenings, classic menswear offers a variety of trouser options that blend comfort with style. In general, however, you should plan to wear long trousers to match the elevated formality and dignity of the evening. Linen pants are a perennial favorite, providing breathability and a relaxed fit perfect for warmer climates. For a more structured look, chinos in neutral colors such as beige, navy, or light gray can be both versatile and elegant. If the occasion calls for something slightly more formal, lightweight wool trousers offer sophistication without sacrificing comfort.

Dress Shoes

In the evenings, your Resort Attire shoes should always be close-toed and, ideally, lace-up or with a full vamp, such as a monk strap. For upscale dining at the resort, a pair of dress shoes such as oxfords or derby shoes may be required. Select a breathable material like perforated leather to stay comfortable in warmer climates. You could also consider a bold pair of shoes, like Spectators or white bucks.

Accessories

Accessorizing evening resort attire is all about striking a balance between elegance and ease. A leather belt matching your shoes can seamlessly tie your outfit together. Consider a statement watch or a simple bracelet to add a touch of sophistication to your wrist. For those opting for a jacket, a pocket square can introduce a pop of color or pattern without overwhelming the ensemble. Over-the-calf socks should always be worn if you’re wearing dress shoes, but they can be in bolder colors to suit the whimsy of the overall dress code. Remember, accessories should complement, not dominate, so choose pieces that reflect your personal style and the relaxed ambiance of your surroundings.

What about

Warm-Weather Black Tie?

“Formal” Resort Attire is distinct from Warm-Weather Formal Evening Attire, which is a variety of Black Tie.

Learn the Difference!

Conclusion

Curating the perfect resort attire is an artful blend of comfort, style, and situational appropriateness. Classic menswear for such occasions should offer a relaxed yet refined aesthetic, allowing for seamless transitions from daytime exploration to nighttime sophistication. By selecting the right trousers, deciding on jacket appropriateness, and tastefully accessorizing, one can achieve a look that is both effortlessly chic and perfectly suited to the resort environment. Remember, the key to nailing this sartorial challenge lies in the details and understanding that true style does not shout, but rather whispers with an air of understated confidence and timeless appeal.

Let us know in the comments about some of your favorite Resort Attire looks. 

Outfit Rundown

Raphael has donned a long-sleeved polo shirt with a collar, which he pairs with a tie to exhibit the full range of the ensemble. He could have easily skipped the tie and still looked impeccable. His jacket bears a resemblance to seersucker but stands out with its checkered pattern—a small yet distinct design that sets it apart from the conventional business suit.

The tie Raphael has chosen is a red and blue shantung, harmoniously echoing the blue hues of his jacket, while his pocket square features hand-rolled edges and x stitches, adding a touch of artisanal craftsmanship.

He’s opted for bold red pants that are reminiscent of Nantucket red but a shade darker, crafted from 100% cotton, making them ideal for warmer climates. To complement the white elements in his shirt and jacket, Raphael selected white buckskin shoes accented with red shoelaces, effectively tying the outfit together with the pants. It’s a statement look, and for those less inclined towards such vibrancy, he suggests that the same ensemble sans tie, paired with medium brown oxfords, would present an entirely different, subtler aesthetic, even with the red pants.

For socks, Raphael is wearing red and blue shadow stripe socks, which integrate the outfit’s color scheme. Sunglasses are an essential accessory for daytime wear, so he doesn’t overlook them. And for added style and protection against the sun, he recommends carrying a Panama hat, which not only looks stylish but also provides shade for the face.

Fort Belvedere

Shantung Striped Dark Red, Blue and White Silk Tie

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Fort Belvedere

Dark Blue Linen Pocket Square with White Handrolled X Stitch

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Fort Belvedere

Midnight Blue and Burgundy Shadow Stripe Ribbed Socks

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Read on to find out!

What Did Men Wear in the 1920s? Decoding the Roaring Twenties Style

Have you ever wondered what men truly wore in the past? In our “What Men REALLY Wore” series, we delve into the sartorial choices of different eras.

In the 1900s

In the 1910s

In the 1930s

In the 1940s

In the 1950s

In the 1960s

Here, we’ll focus on 1920s menswear, examining the changing silhouettes, fabrics, and trends that defined the roaring twenties in men’s fashion.

World War I was over, freedom, celebration, and frivolity ensued, and young people simply enjoyed their lives and the moment. People wanted to dress up again. Along with partying and dancing, fashion was rapidly evolving, not just for women, who had just recently gained the right to vote, but also for men.

Fashion has become a means to express oneself through style.

No longer did you have to wear tones of green, brown, and khaki. But, you could pick up whatever you wanted and just say, “This is who I am. This is how I feel. And I’m enjoying life.” 

Common Misconceptions about 1920s Style and Clothes

Before we proceed, let’s first deal with some misconceptions about 1920s style and clothes. Maybe you’ve watched a virally popular video from Glam about 100 years of men’s fashion. While the production crew was excellent, the subject matter and the clothes were mostly inaccurate.

Maybe you’ve watched some gangster movies or maybe Boardwalk Empire, and you think all that men wore back then were pinstripe suits and Tommy guns.

No, they didn’t, really. Instead, we promise to talk about what real men were back then. Of course, different countries have different climates and different clothing traditions. We focus here mostly on the US and compare it to Europe.

What Were Popular 1920s Men’s Hats?

Regarding headwear, the 1920s were still quite interesting for men because almost everyone wore them. Hat styles hadn’t changed much since the Edwardian era, and you still had people wear top hats sometimes. Even the bowler hat was still worn. Of course, more so in England than in the US.

Fedora: The Most Popular Hat of the Decade

The most popular hat of the decade was definitely the fedora. While most people today would look at a man wearing a fedora as being quite formally dressed, at the time, the fedora was a casual alternative. It had a snap brim because the felt was soft and not stiff and starched. It was much floppier and was crushable, and you could adjust the creases, which made it popular back then.

Even though you can still find fedoras today, 1920s fedoras typically had narrower or shorter brims and higher crowns. Regarding the hatbands, they were often quite wide, and regular working-class men wore them every day.

Looking at all the photographs from the 1920s, you can see that the shape of each fedora is slightly different because a man individually shaped it. It wasn’t just a factory shape that you got and wore that way. You just made the hat and its particular style your own.

Pancake-like One-piece Flat Cap

Another casual hat was the flat cap. Unlike what you see on Peaky Blinders, not all flat caps were 8-piece ones with a wide brim.

casual men’s headwear of the 1920

Flat Cap

The most popular style was the pancake-like one-piece flat cap, which meant it was round and flat on top. It was also a bit wider and more like a beret than what the same style of flat cap would look like today. It came in many styles, including tweed, wool, linen, and cotton, and in many different patterns, such as houndstooth, Prince of Wales check, Donegal tweeds, and so forth.

The Newsboy Cap for the Working-Class

The newsboy cap, a close relative of the flat cap, also rose to fame in the 1920s. With its full, rounded shape and short brim, it offered a slightly more structured look than the flat cap. Often made from tweed or wool, newsboy caps were favored by working-class men and, of course, the paperboys that inspired its name.

Straw Boater as the 20′ Summertime Essential

For summertime style, the straw boater was king. These stiff, flat-topped hats with their jaunty bands projected a carefree and relaxed air, perfect for warm weather and leisure activities.

The Impact of WWI on 20’s Facial Hair Trends

So, what about 1920s facial hair, you might wonder? During the Edwardian and Victorian eras, a mustache was the height of manliness.

During World War I, toxic and lethal gas was used like never before, and the Piccadilly whisker often prevented people from quickly putting on their gas masks. So, it wasn’t as popular anymore. Similarly to 2021, having a beard really impedes wearing masks effectively. Because of that, soldiers were told to shave out their beards so that the gas mask would work more efficiently.

So, when men returned from the war and settled back into their lives in the 1920s, they were used to just shaving every day and not having any facial hair. If men wanted facial hair, you saw a little mustache. But, you didn’t see much hair on your chin, which was typically something only worn by older men at the time.

What Kind of Suits Did Men Wear in the 1920s? Fitted and Sleek, but Still Heavy

The 1920s saw a significant shift in men’s suits.

The jackets of the ’20s were cut much more closely to the body to accentuate the natural waist. If you look at them today, they’re much closer to a body coat than a modern suit.

The buttoning stance was a bit lower than the 19-teens, and it had about two to three buttons. Sometimes, the fronts of jackets were cut away and probably inspired by morning coats.

Suit Fabrics: Wool, Silk, Tweed

The most popular fabric was, of course, sheep’s wool, but they were a lot heavier than what you could get today, and the finish was a lot coarser.

The jacket’s body was usually lined in silk, and the sleeves were cotton because you needed something a bit more sturdy in your arms, which is where you typically wear things out first. Also, because you sweat a little bit more on the arms, things are more likely to get soiled or dirty in that part.

Tweed was a really popular material for country wear.

For summer, you also had cotton and linen suits. The fabrics were slightly less stiff and lighter weight at the time, but compared to today, they were still heavyweights.

In the 19-teens and maybe early ’20s, you might have seen jackets that had a bit more of a cutaway front. But, as the decade progressed, they became more closed, which is more in line with what you know from a modern suit. The fronts weren’t fully square, but they were definitely more square than before.

Frankly, if you look at those suits, they’re very similar to modern business suits.

Jacket with a cutaway front (1910 to early 1920)

Jacket with a closed and square front (1920s)

Modern business suit

Suit Patterns & Details: Subtle Stripes, Tweeds, and Evolving Styles

As for patterns, plain, tweeds, smaller micro patterns, windowpanes, and stripes were all around. Subtle pinstripes were particularly popular, which explains their omnipresence in gangster movies. 

If you look at their jackets, you can definitely see a higher buttoning point, more around the area of your sternum. While in the early 20s, the waist was much higher overall, by the late 20s, you can see a lower buttoning stance and wider lapels, which makes it look more like suits or jackets from 2020.

The clothes enthusiast in you will recognize their subtle differences. Just compare the gorge height, the shape of the lapel, pockets, vents, lengths, and fabric, and you’ll see the difference,  but Joe Average on the street would likely not spot them.

Typically, the sleeve cuffs at about three buttons were spaced much more widely and more like the 19-teens than they’re spaced today. However, there was no cuff stitch–that was truly something of the Edwardian period.

Unlike today, most jackets back then had no vents because they made them look sleeker, even though when you put your hand in your pocket, your bum might have been slightly exposed. Overall, I really enjoy the fabric choices of the decade. They’re often darker, but they have subtle underpatterns and different colors, which create this rich depth that is harder to find these days.

The “Jazz Suit”

Another popular style of the 1920s was the so-called “jazz suit.” Its defining features were its very slim silhouettes and very high waists, which were intended to give the wearer the ultimate hourglass shape.

At the time, these were novelty suits marketed to young men and worn by young men. Often, it had slanted pockets, which created a certain dynamic that was pretty much in line with the hourglass shape. Of course, they had more darts to get this really suppressed shape. Sometimes, they even had belts like a Norfolk jacket, which would help you accentuate the waist even more.

’20s Shirts: Softer with More Attached Collars

The ’20s weren’t too dissimilar from the 1910s in terms of day shirts. Overall, you could still find detachable collars. Typically, older men or upper-class gentlemen would prefer them. Younger men would want the softer turndown collar. Sometimes, also an attached one.

Cuff-wise, you had single cuffs for cufflinks, French cuffs or double cuffs for cufflinks, and single barrel cuffs that were buttoned with buttons. Some men still wore starched bib fronts that were attached to shirts, but they were nowhere near as popular as they used to be in previous decades.

While in Europe, you could still see many detachable collar shirts, in the US, men preferred a shirt with an attached collar and an attached cuff and attached bosoms, and it was overall a more casual shirt. But, it was much closer to the shirt that we were today than the previous decade. Even for Joe Average, it was now affordable to get a striped shirt where everything was attached.

The collars, especially the turndown ones, were not as high as in previous decades. You also had a trend of the soft collar. So, previously, they were heavily starched and polished. These modern collars were not starched, were made out of the same fabric as the body, and they had longer tips that were, of course, a lot more floppy because there was no stability from the starch.

You could also find detachable soft turndown collars, and sometimes they were made in the same fabric as the shirt, or they could be contrasting.

If you’ve watched shows set in the 1920s, like Boardwalk Empire, you see that many men wear collar pins and clips. Men still wore them with ties, though, so the collar clip became really popular. It held the collar tips down, elevated the tie knot slightly, and was just a fashionable look overall. 

Personally, I think it’s a very stylish look that is different from what most men wear today. And if you’re interested in it, we have a great selection of those in the Fort Belvedere shop.

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Collar Pin Cube End Gold Fort Belvedere

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Collar Pin Hexagonal End Gold Fort Belvedere

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Collar Pin Safety Pin Gold Fort Belvedere

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Collar Pin Safety Pin Silver Fort Belvedere

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Collar Bar Clip in Yellow Gold For Classic Narrow Spread Collars by Fort Belvedere

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Collar Bar Clip in Platinum Silver For Classic Narrow Spread Collars by Fort Belvedere

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1920s Waistcoats and Vests: Now Optional, with a New Cut

Waistcoats or vests were no longer mandatory in the 1920s, and you could see men out and about skipping them altogether. That was especially true during the summer months. If men still wore waistcoats, they were typically cut lower.

Remember, in the 1910s, they were cut really high. In the ’20s, you would see more of the V, more of the tie, and more of the shirt front. The waistcoat’s bottom also started to create longer, pointier tips, which led to leaving the bottom button of the waistcoat undone. In the US then, though, men might not have caught on to that fashion yet and buttoned their waistcoats all the way down.

Overall, if men wore vests, they matched the suit, so you had a proper three-piece suit. But you could also find odd vests, creating a slightly more casual look.

As you know, I’m a big fan of waistcoats and vests, especially odd ones. With very little money, you can make an outfit look completely different, and if you want to learn more about that, you’ll surely find our guide to wearing vests enjoyable.

get the guide here

Trousers/Pants/Slacks in the 1920s: Still Slim Overall

Starting in the 1900s, belts became more popular in America, taking over from side adjusters and suspenders. Across the pond in the UK and most of Europe, suspenders were still probably the number one means of keeping pants in the proper position. Nevertheless, belts were catching on there as well.

At the start of the ’20s, trouser fashion was still heavily influenced by the Edwardian era “drainpipe” style, which was very slim and tapered towards the bottom. But remember, they didn’t have pleats. In the mid-’20s, you actually started seeing single pleats in pants.

the rise of

Single Pleats

The idea was to help with the drape of a pressed trouser leg. As you know, when you have a nice crease, and you wear it, and you sit, that crease becomes less pronounced. By having a pleat, you have a nice crease for a longer time, making everything look better.

If you look at the cuffs from the period, they were neither very slim nor very tall. They were relatively modest. I would guess between one and one and a half inches. Towards the end of the decade, trouser legs had gotten slightly bigger at the bottom but were still quite tapered. 

Vintage enthusiasts may be familiar with the trend of students at the University of Oxford wearing excessively wide trousers, which started in the mid-1920s. Even though you can find plenty of pictures of impressively baggy Oxford bags out there, in the ’20s, they were typically around 23 inches. This trend continued into the 40s and 50s. 

I think the biggest pant leg I’ve seen was 43 inches. I mean, at that point, you might as well wear a skirt or maybe a kilt!

What Kind of Shoes Did Men Wear in the 1920s?

In terms of footwear, boots were slightly less popular in the 1920s than in the 1910s. Streets had gotten better; there were fewer horses and less manure on the streets, so it was okay to have regular Oxfords or brogues or, for that matter, spectators.

Two-tone shoes

Two-tone shoes were definitely more popular than they are today, but it’s not like every man wore them. If you just look at their style, you’ll think, “Oh, they wear Oxfords. We wear Oxfords!” But, if you go into the details, you can see they had a higher heel, and the toe had typically a more rounded shape.

Also, the broguing was sometimes a little smaller, the stitching was a little neater, and vintage shoes were a bit different overall from what you see today.

The quality of shoes the average man wore was a lot higher back then than today. Most men would still wear dress shoes, there were no real sneakers, and production happened in the US or Europe. We haven’t had this globalized economy quite yet where we could make really cheap shoes in places.

Chuck Taylors or Converse

Even though rubber sole shoes date back to the 1870s in Britain, “Chuck Taylors” or Converse All-Stars were invented during the 1920s.

A lot of people look at Chuck Taylor’s All-Stars as an all-purpose shoe today. But, back then, it was specifically designed for basketball. It was supposed to be more flexible in the ankle and prevent skidding or sliding around when playing the sport. Most men would not have worn those shoes on the street just to walk around.

What Were Popular 1920s Men’s Accessories?

Canes: From Walking Aid to Fashion Statement

Today, if a man has a cane, it’s typically for practical or utilitarian purposes. In the ’20s, though, men would carry canes for decorative purposes. It truly was a fashion item, and, of course, it had to have the right length. Some were flexible, others were stiff, and some had elaborate decorations, maybe built-in flasks, knives, etc.

Pocket Squares: Silk Adds Style and Choice

Regarding pocket squares, the mass manufacturing of items allowed the introduction of silk pocket squares to a broader range of men. So, they no longer had to wear just plain white cotton or linen squares. They could have printed silk squares.

Fort Belvedere

Burnt Orange Silk Pocket Square with Dotted Motifs and Paisley – Fort Belvedere

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Red Silk Pocket Square with Dotted Motifs and Paisley – Fort Belvedere

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Purple Silk Pocket Square with Dotted Motifs and Paisley – Fort Belvedere

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Timepieces: The Rise of the Wristwatch

When it came to timepieces, the pocket watch with the watch chain was still popular, but wristwatches definitely gained ground. And it makes sense as men wore fewer and fewer waistcoats, there was no natural spot for their pocket watch, so they just wore a wristwatch instead.

Eyewear: Affordable Style with Celluloid

In terms of eyewear, the invention of celluloid, which originated in 1856 as one of the earliest thermoplastics, really helped to create more styles than during the Edwardian era.

While it was first used for film stock, it was later utilized to replicate tortoiseshell, ivory, or horn products. That meant that even working-class men could get the latest-looking style without having to spend the big bucks that they previously would have to.

It was really much like the trend of gold-filled or rolled gold jewelry, which looked like a solid gold piece, but it was a lot more affordable even to the average man.

Of course, you could still find wireframe glasses, sometimes even covered in celluloid. But, you could also find frames that were fully made from celluloid itself.

The actor Harold Lloyd was known for popularizing the imitation celluloid glasses resembling horn or tortoiseshell.

Neckwear: Easier Tying, Bolder Styles

When it came to neckwear, ties and bow ties were still popular in the 1920s. Compared to the previous decade of the 1910s, bow ties had gotten slightly bigger. Also, because the collar of the shirts had become softer, it was easier to tie a tie yourself.

In the previous decade, you could have still found more clip-on ties or pre-tied ties because it was harder to put them on in a stiff collar. But, now, with a softer collar, it was easy-peasy.

The style of the tie changed sometimes and looked more like a modern knit tie with a solid width or just a slightly more graduating width because, again, it was easier to tie them.

Overall, ties looked less like an ascot from the previous decade and more like the tie you know today. That being said, ties back then were much lighter in construction. They often had no lining or were very lightly lined, and they were also, again, shorter than ties are today.

Interestingly, ties often also had unfinished edges on the blade. It wasn’t until the mid-’20s that interlinings became somewhat more popular or introduced into tie production. Style-wise, the ties were bold, colorful, and interesting.

In the ’20s, there was also a boom for the regimental or club ties. And if you think about it, it made sense. A void was left by the end of active service, and by being a club member or having some association, you felt like you belonged to something.

Black Tie & Formalwear in the Roaring Twenties

Morning Wear

By 1920, the rules for morning wear were well-established, but they definitely declined in popularity. The full morning code outfit was worn for celebratory or special events, not for a regular business Tuesday.

There was a slight change in style in previous decades. You saw morning coats that sometimes had two or three buttons. And now, you saw more one or two-button morning coats. Also, previously, you might have seen solid pants or maybe glen check pants. At the time, the striped pants with morning wear were solidly established.

Evening Wear

In terms of evening wear, White Tie was reserved for galas, dinners, or special occasions. At the same time, Black Tie was quite a bit more popular.

As it was still in somewhat of a transitional period, you would often see the Black Tie ensemble being worn with a stiff evening shirt, previously one with White Tie, and likewise, the Marcella starched waistcoat.

White Tie Guide

Black Tie Guide

1920s Casual Menswear Trends: From Knitwear to Swimwear

While formal suits remained essential for formal occasions, the 1920s ushered in a notable shift towards a more relaxed and comfortable approach to men’s casual attire. This transformation manifested in several key areas, redefining the fashion landscape of the era.

1

Knitwear Takes Center Stage

Sweaters emerged as a stylish and practical favorite amid the colorful tapestry of 1920s men’s fashion. The silhouettes gravitated toward V-neck pullovers and cardigans, some even venturing into buttonless, free-form designs with generous shawl collars. This marked a departure from the stiff formality of previous decades, embracing a softer, more comfortable aesthetic.

2

The Rise of Sportswear

The rising popularity of sports and leisure activities in the 1920s significantly influenced men’s casual attire. Golf courses, tennis courts, and boat decks became the new runways, showcasing men in comfortable yet stylish sportswear such as sweaters, pleated trousers, knickerbockers, and sporty blazers.

3

The Automobile's Influence

The increasing popularity of the automobile also influenced men’s casual attire. Driving required practical clothing, and as more men took to the roads, driving caps, goggles, and duster coats became fashionable accessories that signified a modern, mobile lifestyle.

4

Bathing Suits & Terry Cloth Robes

With the rise of beach culture, bathing suits, and terry cloth robes became popular for seaside leisure. Men embraced more relaxed fits and vibrant patterns in their swimwear, signifying a shift towards comfort and self-expression in all aspects of their wardrobe.

The Timeless Appeal of 1920s Men’s Fashion 

To summarize, the Roaring Twenties saw a surge in men’s fashion trends characterized by elegance, sophistication, and practicality. This was fueled by the cultural revolution of the Jazz Age and Harlem Renaissance when Jazz musicians and artists influenced a shift towards casual menswear with their bold embrace of vibrant colors, patterns, and individuality.

Accessories like the versatile fedora and the charming newsboy cap became staples, while the rise of patterns, prints, and relaxed styles mirrored the changing cultural landscape and a yearning for self-expression.

men’s fashion icon during the 1920

Rudolph Valentino

Icons like Rudolph Valentino, “The Latin Lover,” and Douglas Fairbanks Jr. “The King of Old Hollywood” further fueled this fashion revolution. Valentino’s sleek suits, wide-legged trousers, and dramatic accessories inspired men to add a touch of romantic flair to their wardrobes.

men’s fashion icon during the 1920

Douglas Fairbanks Jr

At the same time, Fairbanks’ tailored sportswear and adventurous spirit encouraged a sense of dynamism and confidence in everyday attire. Even today, glimpses of their influence can be seen in modern menswear, from the enduring popularity of well-tailored suits to the resurgence of bolder patterns and accessories.

Overall, the ’20s were a lot of fun, and if you like the style, a great way to experience the visual flair of the period is through the German series Babylon Berlin. While not entirely historically accurate, the show offers a captivating glimpse into the era’s fashion, showcasing familiar and unexpected styles.

What to Wear To a Roaring 20’s Party: Steal This Style

If you’re wondering what men wore to a 1920s party, let me share an outfit inspired by the era.

It consists of a white shirt with a barrel button cuff, complemented by a darker tie in silk with a micro pattern. Adding to the ensemble is an off-white tennis sweater with dark navy elements on the v-neck, bottom, and cuffs.

Fort Belvedere

Orange and Navy Blue Two Tone Solid Oxford Socks Fil d'Ecosse Cotton – Fort Belvedere

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Fort Belvedere

Light Gray Shoelaces Round Luxury Waxed Cotton Dress Shoe Laces by Fort Belvedere

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Fort Belvedere

Navy Blue Silk Wool Pocket Square with Printed geometric medallions in green, blue and orange with off-white contrast edge – Fort Belvedere

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I mean, without the jacket, people play tennis in that. Can you believe it? The tweed jacket is orange, and it has stripes in green and yellow. It’s very bold and fun. And I thought it worked well with my white flannel trousers. In fact, they’re more off-white. As you know, I’m a fan of pleats. So, I have two pleats, which again are not quite 1920s. But, a single pleat would have been definitely 1920s.

My cuffs are maybe a little bigger than in the 1920s, but I wear a pair of leather shoes. Here, they’re full-brogue derby shoes. I put in contrasting shoelaces to pick up the lighter-colored theme. My socks are orange and blue from Fort Belvedere, they pick up the color of the jacket.

You can find them in our shop, just like the silk wool pocket square, which is blue with green and off-white micro patterns, trying to tie the entire outfit together with my chosen colors. Last but not least, I have a flat cap, one piece. It’s a modern one, but it has a nice Donegal tweed that picks up the oranges and the greens.

What 1920s style do you find most interesting–and would you wear it today? Let’s talk about it in the comments!