Winchester Shirts (Contrast Collar) & How to Wear Them

Among men’s shirts, perhaps one of the most underrated options is the so-called Winchester style. While not as commonly seen as other shirt styles (especially today), it remains a smart choice–provided you know how to wear it well! As such, here’s our definitive guide to what a Winchester shirt is, where it came from, and how to incorporate it into your outfits.

What is a Winchester Shirt?

In simplest terms, a Winchester shirt is a dress shirt style that is colored, striped, checked, or otherwise patterned, but that has contrasting collar and cuffs (which are almost always white). You can sometimes find models that don’t have contrasting cuffs, but rather that match the body of the shirt. In either case, though, the collar will be contrasting. The advantage of such a shirt style is that it is somewhat more formal, given its white collar and/or cuffs combined with a pop of color and/or pattern in the v-shape between your collar and the lapels of your jacket.

Because of the white features, Winchester shirts are slightly more formal than if they were to simply have a collar and cuffs that both match the shirt’s body. Therefore, they’re well suited to business wear (and less so, casual wear).

Essentially, the Winchester shirt is mimicking fashions of the Victorian era, when men often wore shirts with detachable collars and cuffs, and would mix and match shirt bodies with different colors and patterns. Given that this is a Victorian-inspired look, you will sometimes see Winchester shirts worn with formal daywear, which is an appropriate option.

Winchester styles might also remind you of the 80s power suit look as immortalized by Michael Douglas as Gordon Gekko in the 1987 film Wall Street. We assure you, though, that while these 80s power suits will look dated today, you can still very easily wear a Winchester shirt with a classically-inspired wardrobe and not look out of place.

The History of the Winchester Shirt

The shirt is named after the 52nd Lieutenant Governor of Connecticut, Oliver Fisher Winchester. Of course, this name is more commonly associated with the Winchester rifle, which was developed by his company, the Winchester Repeating Arms Company.

Born in 1810, Winchester started his career as a clothing manufacturer, opening his first men’s furnishing store in 1837. Following this, he moved to New York City ten years later in 1847 and co-founded the Winchester and Davies Shirt Manufacturing Company in 1848.

He would use his profits from these companies to become the majority stockholder of the Volcanic Repeating Arms Company in 1855 and the president by 1856. He eventually bought out and reorganized the company in 1857. He would then reorganize this company a second time before sticking with Winchester Repeating Arms Company, which is when his famous rifle was invented. So, yes, the man behind the rifle and the shirt are one and the same.

So, what about the shirt itself, then?

Winchester and Davies created the Winchester and Davies Shirt Manufacturing Company in 1848. By 1860, they were producing 800 shirts a week, and they paid their machinists more than their hand sewers. This was simply because, by using the sewing machines, the machinists could produce a high-quality shirt in under an hour; whereas, the hand sewers could sometimes take up to 14 hours to produce a single shirt.

While other factories and manufacturers of the time saw machine sewing as cheap and unskilled work, Winchester and Davies capitalized on the speed and efficiency, hiring more machinists and paying them more to maximize production.

By the beginning of the 1930s, the older-style detachable collar shirts were beginning to lose favor, but men still wanted to mix and match their colors. Thus, at this time, the most popular styles of the contrasting shirt collar and cuff with colored bodies were being sold by the Winchester and Davies Company. So, this is most likely why they became known as Winchester shirts.

Why Wear A Winchester Shirt?

Not only do Winchester shirts look slightly more formal than conventional dress shirts, as we mentioned already, but they also give a straightforward visual signal back to the golden age of classic menswear when contrasting collars and cuffs were more common on well-styled gentlemen.

The white cuffs and collar provide nice visual contrast, adding layers to your outfit. Also, in particular, the white collar provides a nice neutral background for a necktie. As the shirt collar and necktie are often a main focal point when wearing a suit, given that they are close to the face, they must harmonize well.

Plain and neutral white dress shirts will pair well with any necktie style, whereas, sometimes, a colored shirt might look a bit too flashy with the rest of the outfit.

However, if you feel that an all-white shirt would be a bit too plain or too formal and you still want to incorporate some color into your shirt, a happy middle ground is to use a Winchester, where you’ll have the plain white collar to frame your necktie along with usually plain white cuffs, but a colored shirt body. Essentially, then, the Winchester shirt can often represent the best of both worlds for many outfit combinations.

What are the Features of a Winchester Shirt? Let’s Start With The Collar!

While the defining feature of a Winchester shirt is its contrasting collar, there are no set rules on what type of collar it must be. Therefore, the Winchester can come in pretty much any style of collar. Since we have produced a comprehensive guide on the different shirt collar styles, we won’t go into too much detail today. So, what follows is a quick rundown of the collar styles we think look particularly smart with a Winchester shirt.

1. Point or Straight Collar

The classic point or straight collar can be paired with several different necktie knots and can also be worn with collar jewelry.

2. Spear Collar

The longer spear or spear point collar also looks good paired with a slimmer tie knot and looks smart when paired with collar jewelry as well.

3. Tab Collar

The tab collar, which features a loop and a tab with a button, will hold the collar down against the shirt body and push the tie knot out, essentially using the same function as collar jewelry.

4. Cutaway Collar

Cutaway collars can be another good option, though we would advise using a larger tie knot to accommodate the wider spread.

5. Button-down Collar

Even though Winchester shirts are generally more formal, you will occasionally see them with button-down style collars as well.

In this case, we would simply recommend that you avoid buttons or button thread that is strongly contrasting as it will detract somewhat from the formality of the Winchester style.

6. Wing Collar

Speaking of formality, at the upper end of the formality scale here would be the wing collar, which can also be found on Winchester shirts, mirroring the detachable styles of the 19th and early 20th centuries.

You won’t have too many opportunities to wear this particular style outside of formal daywear, but be aware that if you are wearing a morning dress, this style is an option.

Colors & Patterns on The Body of Winchester Shirts

Most commonly seen are Winchester shirts with either a plain blue body or a body featuring blue and white stripes. This is a very subtle and safe look. So, if you’re just venturing into the world of Winchester shirts, we’d recommend starting here as the light blue will provide a nice neutral base on which you can build many types of outfits.

Stripes are definitely a favorite among wearers of the Winchester style as they were popular from the Victorian era all the way into the 1930s. And, of course, striped shirt styles persist to this day.

With that said, though, we would recommend that you avoid Winchester styles that contain particularly thick or gaudy stripes in loud and garish colors as these aren’t going to be versatile options to build outfits around. Safer options would include stripes in one color, perhaps in a neutral shade or if you’re going for multiple colors, make sure that the stripes are thinner and finer.

Furthermore, the stripes don’t always have to be against a white backdrop. You could also find Winchester shirts in pastel shades like pink, perhaps with a thin blue stripe for an accent.

While the most common pattern for Winchester shirts you’ll find will be some variation of stripes, there are also checked Winchester shirt styles available. We wouldn’t recommend trying these right away if you’re just starting out with Winchester shirts as their bolder pattern nature can be a bit more difficult to incorporate into your outfits.

To that point, simple patterns like box checks can add some dynamism to an outfit. In contrast, something like a smaller and more subtle gingham will add an element of visual interest without being overpowering and thus, allowing you to experiment more with your accessories and other outfit elements.

Just remember that, in general, the wider and larger a checked pattern, the less formal the shirt is going to be. Micro-check patterns will be safer. And if your check pattern is a bit too wide to be worn well, you could always just repurpose the body of the shirt as a game board for your next game night.

You can, of course, also find Winchester shirts with solid or block-colored bodies as well, and these make a perfect canvas around which you can build outfits and experiment more with your tie and other accessories.

If opting to wear a block-colored Winchester shirt, we’d recommend going with pastel colors such as light blue, yellow, or pink as these are classic and well-worn options in the world of classic menswear.

Again, remember that your shirt is acting as something of a canvas here, serving to complement and add dimension to your suit and your accessories. Therefore, going with something subtle is always going to be a smart choice.

Conversely, though, bright and flamboyant colors in things like electric pink or dark jewel tones are just going to look loud and flashy and will definitely take your outfit more into 1980s power suit territory.

Winchester Shirt Outfit Ideas 

Outfit #1: Classic Navy Business Suit

The first outfit is a more formal business-style outfit with the navy suit grounding the outfit, and it features the Winchester shirt with the most common blue and white striped design.

The light blue of the shirt harmonizes well with the navy tones of the suit, but it also provides a somewhat subtle backdrop for my Fort Belvedere tie, which is in a burgundy shade of jacquard woven silk featuring small white polka dots.

Also in this same color family are my vintage silk pocket square featuring a glen check pattern in burgundy and a very pale light blue and my small dark red carnation boutonniere, which is from Fort Belvedere. Additional Fort Belvedere accessories are my cufflinks, which are in our platinum-plated, sterling silver eagle claw design featuring red carnelian as the stone, to again harmonize with the other accessories.

The tie is framed well by the white collar of the shirt, and the cufflinks are allowed to stand out even more against the white shirt cuffs. The suit jacket’s peak lapels perhaps give just a taste of that 1980s flare while not looking distinctly dated.

This outfit is rounded out by a pair of dark brown, cap-toed Oxford shoes, which are somewhat more formal in nature, and some Fort Belvedere socks in our new two-tone solid designs in varying shades of blue.

Outfit #2: Gray Herringbone Patterned Suit

The next outfit features a gray suit style in a bird’s eye weave with a Winchester shirt with a very subtle herringbone pattern and a blue body.

The subtle herringbone pattern and pastel blue background make for a good canvas for our Fort Belvedere accessories, including a grenadine tie in blue and purple, a blue cornflower boutonniere which, of course, has some purple tones, and a white linen pocket square.

Outfit Example #3: Brown Patterned Suit

Our final outfit here features a brown patterned suit and a Winchester shirt in yellow. We’ve accented it with our Fort Belvedere madder silk tie in orange-red with a micro pattern in buff as well as a boutonniere, which is the orange exotic Caribbean.

The pocket square is in a wool-silk blend in a color we’re calling “antique gold yellow” and features paisleys in beige, blue, red, and orange also with a shoestring edge for more contrast. 

Here, the plain yellow color of the Winchester shirt provides a good base for slightly bolder accessories. And we’ve also capped it off with collar jewelry, given that the collar of this particular Winchester shirt incorporates the use of a collar bar.

The gold-plated, sterling silver eagle claw cufflinks with tiger’s eye as the stone reinforce this same warm color feel and, also, I’m wearing the same shoes as before and a pair of socks with a subtle pattern that also picks up on the same color feel.

Hopefully, by now, we’ve inspired you to try incorporating Winchester shirts into your wardrobe.

Where Can You Buy Winchester Shirts? 

While perhaps not as common as they once were in decades past, Winchester shirts are still somewhat common, so you should be able to find them at your local department store or men’s clothing store.

Still, if you’d like a few specific brand recommendations, we could list Charles Tyrwhitt, a brand we’ve recommended on this channel before, which offers 100% cotton Winchester shirts from around $60 to $90 per shirt.

T.M. Lewin also supplies Winchester shirts in pure cotton that they refer to as “contrast collar shirts.” They sell them for about $65 a shirt. Hawes & Curtis probably has the widest selection of Winchester shirt styles available, at least at the time we’re writing this post. Unsurprisingly, Brooks Brothers also offers Winchester styles from time to time.

The American brand Paul Fredrick commonly offers Winchester shirts, although they can occasionally be quite bold, so exercise your best judgment. If you’re looking at other international brands, Japanese offerings include the brand Suit Company. 

Finally, for something more upscale, Thomas Pink sells Winchester styles typically for around $230 a shirt in a poplin weave, though the fabric composition isn’t listed on their website at this time.

Conclusion

In conclusion, then, we believe that the Winchester shirt may be the perfect shirt option for bringing a bit of color contrast and dynamism to your outfits while still maintaining a formal air with its white collar and cuffs. In this way, it makes for a subtly dynamic background for your other outfit accessories and, again, is something of an underrated shirt style, so we hope we’ve raised its profile today.

Do you have a Winchester shirt in your collection? Share your thoughts (or your style tips) in the comments!