7 Casual Jackets for Men (& How To Style Them!)

The casual jacket is something that, over the years, has become a garment that has many different faces, and is great to incorporate into many outfits dapper outfits, not just for their functionality, but also for aesthetic benefits. Today, we discuss the history of seven casual jacket models and share outfit ideas to look great in them!

To some, they might find casual jackets to be a more traditional-looking jacket with certain prints and colors, which exude a cultural history, and to others, they may find a casual jacket to be something that looks more like a jacket from Barbour or an aviator jacket.

In reality, while these examples are not incorrect, there are actually a number of different jacket styles that fall under the “casual” umbrella. A few examples are the motorcycle or leather jacket, the bomber jacket, the parka, the windbreaker, the Harrington jacket, military-style jackets, and the unstructured sport jacket.

History of Men’s Casual Jackets: 1. Motorcycle Jacket – For Rebels & Riders

The first jacket was introduced in 1928 by Irving Schott, making it the first jacket in the style ever introduced. Many may remember it worn by Marlon Brando in the 1953 film “The Wild One.”

A motorcycle jacket’s main purpose is to protect the wearer in case of an accident. These jackets are now warned for both motorcycle wear, style, and of course, for making a statement. Belstaff’s Trialmaster in waxed cotton and the Panther in leather would also be good examples. 

2. Bomber Jacket – The Outerwear of Pilots

The bomber jacket originated from military clothing and then moved its way into certain subcultures like punk. And most recently, things like high fashion. Notable styles would be the MA-1, the A-2, and the G-1. 

And, somewhat similar to that bomber style, we have the aviator jacket. You see, originally, bomber jackets were once known as “flight jackets,” and were created by the US Army Aviation Board in 1917. Pilots wore these because they were versatile, functional, lightweight, and kept them warm.

3. Parka – Best for Adventures in Cold Weather

A parka or anorak is a type of coat with a hood often lined with fur or faux fur. Invented by the Caribou Inuit, this garment was made from Caribou or seal skin. Historically, parkas were used for hunting or kayaking in the cold arctic temperatures.

Popular brands include Canada Goose and Moncler.

4. Windbreaker – Lightweight for Transitional Weather

This is certainly one of the most casual styles on this list. The windbreaker first became popular in the 1970s, and why is it called a windbreaker? Well, it’s important to note that this term is actually used more in North America and in Japan.

“Windbreaker” was actually a term used by the John Rissman Company out of Chicago for its gabardine jackets. The term “windcheater” is actually used in the UK and other commonwealth countries.

Whichever it is called where you’re from, the keyword here is “wind,” as this type of jacket is used to resist wind chills.

5. Harrington Jacket – Steve McQueen’s Choice

Another casual style with a more classic pedigree is the so-called Harrington jacket, which dates back to the 1930s, but is also famously associated with the “King of Cool,” Steve McQueen.

The origins of this jacket are a bit mysterious though, and there’s a lot more to the story, but our Harrington Jacket guide has you covered on that.

6. Military-Inspired Jackets – For Maximum Utility

Our final outerwear mentions include military-inspired jackets like the safari jacket and the field jacket. These often come in colors like khaki and olive and are known for having a lot of large firm pockets and epaulettes.

Depending on their fabric, color, and styling, they can lean a little bit more formal or a bit more casual.

7. Unstructured Sport Jacket – Where Casual Meets Business

Moving from true outerwear into core menswear pieces, these jackets are known for having little canvassing, little lining, and a thin shoulder. The style of this jacket is lightweight and easy to travel with. It is ideal to wear in the warm summer months, and it’s definitely something I’m more comfortable with.

And when working in retail, I definitely prefer to give this to gentlemen who are more muscular and broad-shouldered. Now that we understand a bit more about these casual jacket styles and why people wore them, it’s a bit easier to understand the differences they have with something like a canvas suit jacket or a wool or cashmere overcoat. These provide a much different look and, due to their construction, sit differently on the body.

General Styling Tips for Casual Jackets

Find Ideal Fits and Colors

As I often like to say, make sure that fit is ideal for your body type. From there, you’ll have a much easier time incorporating a casual jacket into your wardrobe. When it comes to colors, it’s important to keep them fairly neutral and versatile at the beginning of your collection. 

Once you have established a solid base with your collection, if you so choose, you can start incorporating more unique color tones within your collection.

Find Styles with Appropriate Seasonality

It’s important to purchase jackets that are functional for where you live. Although it may seem appealing to own an extremely warm two thousand dollar parka from the trendiest coat brand if, for example, you live in a place where the temperature is on average 75 degrees, how often do you think you’re actually going to wear it? 

In this example, it’s important to find something that is both cost-effective, in line with your style, and of course, temperature appropriate. As I happen to live in a colder climate, it makes sense for me to have a few lighter jackets to layer with and then, of course, a few warmer jackets.

Kyle’s Personal Jacket Suggestions

Over the years, I’ve collected a number of different jackets and certain styles like the bomber, for example, I’ve learned don’t look the best on me. So, I’ve stopped purchasing them. And the more I wear the styles I enjoy, the more they eventually need to be replaced or even removed to make room for something different. 

As my style has changed a bit over time, some jacket styles I’ve stopped wearing altogether, and others I continue to enjoy wearing.

1. Unstructured Sport Jacket

This is absolutely one of the most commonly used styles in my wardrobe. I will often play with layers a bit, and I’ll wear the style in early summer and fall and also in early winter; pairing this with either dress shoes or boots, casual chino pants, or even denim when it’s appropriate. 

2. Lightweight Field Jacket

I really like how the style works within my wardrobe, and I like how the pockets are very helpful when carrying around things like a wallet or phone charger.

The lightweight nature of this jacket is ideal for someone on the go as it is packable, but I can also layer with it.

3. Motorcycle-inspired Jacket

Sometimes I like to layer this in the fall with a light sweater or turtleneck, jeans, and boots. I have outgrown the one that I’ll be showing in the outfit ideas today, which is something that I’ve had for the last few years.

However, I have a new one on order from Boda Skins that I’m very excited to start wearing. 

4. Waxed Cotton Jacket

Another style I have in my collection that I haven’t yet mentioned today is the waxed cotton jacket in black.

Outfit Ideas for Casual Jackets

If you’re wondering how to step up your style with a casual jacket, take inspiration from these outfits ideas that incorporate styles from within my collection. 

Outfit #1: Leather Jacket

First up we have a leather jacket, contrast turtleneck, denim, and boots. This is a very sleek and modern take on dark elements, which makes it very easy to put together. The main outlier here is the contrast turtleneck, which gives a bit of brightness and breaks up the otherwise more monotone vibe you might have been giving off with both a dark jacket, dark denim, and boots.

Try adding a bit more personalization by adding a pair of glasses, a hat, a watch, or even a ring.

Outfit #2: Unstructured Sport Jacket

Another outfit idea is an unstructured sport jacket with a pair of chino pants, a dress shirt, a sweater, and dress shoes. This outfit would look rather preppy and sophisticated or can look extremely busy by you trying to wear every color under the sun. It all depends on how you decide to structure this outfit.

Personally, I find it best to have minimal sources of loud colors within an outfit. The goal here is to call some attention to yourself and then, spark some engagement, but, not to have everyone stop and stare as if you’re someone who’s in the Guinness Book of World Records for wearing every color imaginable.

Having the colors primarily come from the jacket, sweater, and/or shirt, and letting the shoes and pants fall into the background is an ideal way to wear this outfit. 

Outfit #3: Field Jacket

Lastly, we have the field jacket with a button-down shirt, chino pants, and dress shoes. I like to wear this style from time to time. I really enjoy the lightweight nature of the field jacket and, of course, those big extra pockets.

Layering this with a button-down shirt and adding in, maybe, a sweater or a denim jacket is a nice way to mix things up. And switching out chino pants for the denim and wearing a pair of more broken-in boots as opposed to dress shoes are just a few minor ways you can actually add a little bit of personalization to this overall outfit.

Conclusion

Casual jackets have a variety of ways to help you look sharp while also offering you versatility and functionality. From added warmth and protection to, of course, that great pocket storage, there are a variety of casual styles that are going to be helpful to you. Although I found my favorites, it’s important that you take the time to find out what styles inspire you and work best for your wardrobe and, of course, best for your body type.

Outfit Rundown

I’m wearing my green field jacket with a blue and white checked button-down shirt, a pair of tan chino pants, and brown dress shoes. And, of course, a pair of shadow stripe Fort Belvedere socks. For other accessories like these socks, check out the Fort Belvedere shop.

What’s your favorite casual jacket and how do you like to wear it? Share your personal style techniques in the comments!