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The Adult Man History of The Oxford Shirt and How to Wear One Old Textbook With Gentlemen Wearing Oxford Shirts with Text
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The Oxford Shirt: A Style Icon’s History and Modern Wear Guide

Sported by niche subset of wearers to eventually becoming “the people’s shirt,” here’s your key to capitalizing on its handsome appeal.

Karlton has been covering men's style and grooming topics for The Adult Man since 2020. He's also written for other popular men's publications such as The Modest Man and Effortless Gent. Karlton is an LA-born, New York-based lover of culture and optimism. Perpetual watch-wearer. Always holding a martini or a football, Karlton's favorite subjects in school were recess, PE and prom. Read full bio.


Published: Aug 23, 2024
8 min read

When I consult on clothes, there are few garments that I consider a necessity for every client, regardless of lifestyle and personal style.

We’re all different, and I respect that.

However, the Oxford shirt is an exception. Every guy looks good in one, and you can wear it in 99% of dress codes.

So where did this quintessential piece of menswear come from, and how did it achieve such ubiquity? Why does it work so well in almost any context?

Here’s everything you need to know.

Origins: It Started With a Weave

Charles Tyrwhitt oxford and lightweight pants

Before the Oxford shirt came about, the Oxford cloth was invented in the late 1800s.

It was born in the mills of Scotland and was one of several weaves named after prestigious universities. The names were pretty arbitrary, as the Oxford cloth has nothing to do with the school itself.

The Adult Man History of the Oxford Shirt Oxford Cloth Example Up Close

Still, it turned out to be a practical and useful material. We don’t use the Harvard cloth, whatever it was, anymore.

But the Oxford cloth was, and is, made with an equal number of vertical and horizontal cotton threads, otherwise known as a conventional basketweave. The result is a fabric that balances softness with durability better than any other fabric ever did at the time of its inception.

Naturally, this made it perfect for sports.

Sporty Beginnings

Model wearing Ben Sherman Brighton Oxford 3

As with the Jaeger-LeCoultre Reverso, you can thank the sport of polo for the proliferation of the Oxford shirt. British polo players in India, who had to endure chukkers under the South Asian sun, loved that the fabric was soft and cool, yet strong enough to endure the intensity of the game.

Up until the Oxford, there were two kinds of shirts: Lightweight formal shirts that were less durable, and sporty workshirts that were heavy duty but less breathable. So, the Oxford was cut into the shape of a business shirt, collars and all, and used on the field. Buttons were used to secure the points so they didn’t fly out of place during the game.

Frank and Oak oxford shirt tucked into Rhone chinos

As such, the first Oxford button-ups were, in fact, button-downs

Though most sports today call for modern performance fabrics, a button-down still has a sportier aesthetic than a button-up because of its origins. 

You can wear a short-sleeve button-down Oxford as a classier counterpart to a t-shirt in a casual outfit. In fact, if you go for a washed version, like Charles Tyrwhitt’s, you can even wear it to a golf game or while fishing.

Coming to America

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Brooks Brothers invented, or at least popularized, the Oxford shirt as we know it today. Supposedly, John Brooks saw the prototype shirts while in England, likely while watching a polo match.

The Brooks Brothers Oxford cloth button-down, or OCBD, featured a rolled, unlined collar. It was softer and less stiff than the collar of a business shirt.

This made it different from the detachable collars common on similarly silhouetted shirts at the turn of the century. Meanwhile, the pleated back allowed for a wider range of movement.

The Rise of the Oxford Shirt

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Businessmen who wanted something more comfortable than a regular business shirt turned to the Oxford button-down. Eventually, it became as common as its stiffer counterpart.

Of course, it was always the less formal of the two. By the 1950s, it was a weekend and college campus mainstay.

Then, the pendulum swung away from casualness. In the ‘80s, Brooks Brothers themselves added more structure to their Oxford. They lined and fused the collar and even made non-button-down versions.

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Today, there are Oxford button-ups and Oxford button-downs. Men often wear them indiscriminately with their suits.

A button-down can never truly be considered formal. It’s not a shirt you can wear at a black tie optional event. However, most won’t bat an eye when it’s worn with proper business attire.

For instance, in most offices, this white Charles Tyrwhitt button-up and this white button-down would register as being equally formal to most people.

Charles Tyrwhitt Non-Iron Royal Oxford Shirt

Crafted from 100% pure cotton, this Oxford is soft and durable with the kind of stretch you'd find in a synthetic blend. Whether it be jeans, chinos, or even your favorite swim trunks, it pairs effortlessly with anything below the waist for a polished ensemble. And not having to iron it? Effortless all around.

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Varieties: The World of Oxford Shirts Today 

The Traditional OCBD

KOTN oxford shirt and jeans

The traditional Oxford cotton button-down is still the most common shirt made with the defining basket-weave fabric. It’s smoother and less shiny than a formal dress shirt and usually has an unlined collar and cuffs.

It often features a back pleat to provide extra mobility, as well as pleats on the arm where the sleeve meets the cuffs. The shirt may also have a chest pocket.

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Even within the OCBD, there’s a range. Some are more structured than others, for a slightly more formal look.

Those with visible stitching at the edges of the collars and at the shirt placket (where you button your shirt up) are more casual. The extra stitching provides more fortification but also gives the shirt a more workwear aesthetic, similar to what you’d find on a denim shirt or Western shirt.

Charles Tyrwhitt washed

For example, take a look at Charles Tyrwhitt’s Non-Iron Oxford Shirt in sky blue. Now compare it to their Stretch Washed Oxford, also in blue. Both are elegant with similar silhouettes, but the latter shirt’s visible fortification stitching gives it a more rugged feel.

The Oxford Button-Up

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The Oxford button-up is just the non-button-down cousin to the OCBD. Although they can be styled similarly, the Oxford button-up is considered more formal.

Remember, fewer details equals a cleaner look, which equals a dressier garment.

Since the collar points can’t be buttoned down, an Oxford button-up usually has more structure in the collar. This isn’t always the case though. Some collars are meant to sit flat, similar to a camp collar.

A well-structured, pocketless Oxford button-up can, for the most part, take the place of a traditional dress shirt.

Short-Sleeved Oxford Shirts

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Short-sleeved Oxford shirts come in button-up and button-down varieties. They’re a great summer and spring option and a good alternative to a regular t-shirt.

The added architecture of the collar, compared to a crewneck, makes any casual outfit look more grown-up. And if you stick to button-downs, you achieve this more together look without any added stuffiness.

Moreover, a short-sleeve Oxford effectively adds class and sophistication to a warm-weather vacation outfit.

Patterned Oxford Shirts

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The most common patterns you’ll find on an Oxford are checks and stripes. This is partly because they’re easier to weave in because of their geometric nature.

However, because of advancements in printing technology, there are also graphic options. Some are novelty items more than anything, while others can feature a classy, subtle motif.

A shirt with small anchor prints would go well with shorts and boat shoes. An Oxford with, say, a bird or hunting dog motif would look natural with a Norfolk jacket and hunting boots.

Collarless and Mandarin Collars

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A collarless Oxford shirt is more sophisticated than a crewneck long-sleeve tee but less stuffy than a spread collar. It’s different enough to add distinction to your wardrobe but not weirdly different.

Charles Tyrwhitt makes an excellent collarless Oxford, which I love because few traditional dress shirt brands do. I like their model because the collarless collar isn’t too low or too high. Plus, it comes in traditional blue and white, as well as a striped version.

Charles Tyrwhitt Collarless Stretch Washed Oxford Shirt

Made from midweight cotton, this Oxford shirt is a stylish twist on a classic. With its crisp ocean-blue stripes and mitre-edge cuffs, it offers a modern yet relaxed look that’s perfect for dialed-down sophistication.

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Some collarless shirts, like Charles Tyrwhitt version above, come with a buttoned top, while others don’t for a more Mandarn-inspired look.

How to Wear an Oxford Shirt

KOTN oxford shirt

Truly, there are very few wrong ways to wear an Oxford shirt.

Don’t wear it with athletic performance shorts and trainers when you’re at the gym. And don’t wear it with a black-tie or white-tie tuxedo. Even then, in a pinch, you may just be able to pull off a white Oxford button-up in certain black-tie situations if the shirt is lightly woven and structured enough.

Take any casual t-shirt outfit, such as with a combination of sneakers with shorts or jeans, and replace it with an OCBD. With that one switch, you’ll have elevated the outfit considerably.

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White low-top sneakers are perfect for a cool, effortless look. However, a pair of suede or leather loafers adds classic chicness.

In the summer, I like Oxford shirts with a sun-faded hue—a muted rust or a light chambray color, for example.

Oxfords are also an effective way to bring a formal outfit down to earth.

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Take any suit combo, whether that’s a full suit or a broken suit, and replace the dress shirt with a button-down. Even with a tie, it’ll look much less stuffy. You can even go for a shirt with a fun pattern, and temper it with a neutral suit, perhaps in charcoal.

My main advice for dressier Oxford button-ups is to find an easy-care one, like the Charles Tyrwhitt Non-Iron Royal Oxford. It looks formal but is impressively no-fuss.

Conclusion

We’ve come a long way from the days Oxfords were used as polo shirts. 

The best part is that they go with any personal style, whether you’re dressy or sporty, traditional or fashion-forward.

It’s all about how you style them.

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