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Miles Davis wearing a green oxford cloth button down shirt

The Story of the Oxford Cloth Button Down Shirt

As far as essentials in a man’s wardrobe go, there are fewer worthy contenders for the sartorial hall of fame than the Oxford Cloth Button Down (OCBD).

You’d think it almost impossible that any single piece of clothing can exude all the qualities that most men seek and approve of. Yet, the OCBD does it all in one stroke. Casualness, professionalism, sport, youth, education and dependability all effortlessly ooze out of this all-time classic.

No ode to the absolute dependables in men’s fashion can possibly be complete without a few hundred verses about the OCBD. That’s why in this article, we’ll take you through all things OCBD, including how it came about and how to wear it.

The enigmatic Oxford Cloth Button Down shirt

As the name implies, the OCBD is made out of Oxford cloth. The fabric is made of a distinctive weave which, though similar to a plain canvas weave, uses several yarns woven together instead of individually. This produces a breathable cotton garment with a textured finish.

Although many points about the shirt have changed with time, two enduring traits linger. The shirt is made out of Oxford cloth and features button-down collar points. The second, and most important trait, is a genuine OCBD has a distinctive collar roll that creates an “S” shape (more on this later).

Perhaps the greatest allure of the iconic shirt is its simple versatility. It provides a rock solid option when you’re faced with the tricky decision of what to wear on a semi-formal occasion. Perfectly straddling the fence between casual and formal, a well-tailored OCBD can help you turn up chic and yet rack up points for suave style.

Man wearing ocbd, patterned tie and barbour waxed jacket
Source: Menswear Musings

Whether you’re going for a dressed down tweed or looking for a light cotton to go with your trusty selvedge denims, the OCBD never looks out of place. And if you’re in the mood to pull it off, the shirt can feel just as natural in the boardroom as it does in the barroom.

As you will see in a bit, the OCBD is steeped in history. From its American roots in the tailoring halls of Brooks Brothers, up to its introduction in England, it has a long and storied pedigree. Some of the most recognizable style icons and celebrity names have embraced the shirt, guaranteeing the OCBD a permanent spot in the menswear hall of fame.

The History of the Oxford Cloth Button Down

Everybody and their brother seems to have tried out the OCBD. John F. Kennedy, Paul Newman, Michael Caine and Steve McQueen are just some of the names on a very distinguished honor role. But what exactly is it that made the OCBD such a staple of menswear down the years? Here’s a bit of history.

The Oxford Cloth Button Down started out sort of like an accident. In 1896, John E. Brooks, the grandson of Brooks Brothers’ founder Henry Sands Brooks, got the idea for the shirt while watching polo in England. He noticed that the players were wearing shirts with their collar tips secured to the front.

This was a necessity at the time since polo shirt collars were pretty big jobs then. To keep the shirt from flapping in the players’ faces, they needed to be secured. This was done with different items including buttons, collar pins and, that old staple, heavy starch.

Brooks was enamored with the style on sight and he immediately procured a sample for local production back in the states. The shirts went on sale in 1900 and were initially produced as ready-made sport shirts advertised as “Polo shirts”. In short order, the store began putting the button-down collar on Oxford shirts and so was the OCBD born. The rest, as they say, is history.

By 1915, you could hardly walk two blocks without spotting a stylish OCBD and by the 1950s the shirt style had made it back across the English Channel. It was made popular in British pop culture by youth movements such as the mods, and from there, the invasion was complete.

Alain Delon wearing an oxford cloth button down shirt
Alain Delon
Gianni Agnelli wearing an ocbd shirt
Gianni Agnelli

Today, pretty much everybody that is somebody has stepped out in an OCBD. Gianni Agnelli, head of Italian car giant Fiat, was known as a man with the predilection and means to dress well, widely regarded as one of the best dressed men of the 20th century. He loved himself an OCBD and even affected his own rakish style by leaving the collar buttons undone. Bob Newhart was so enamored with the shirt style he named his first record album after it and Alain Delon smoldered in the shirt way back in 1960 as Tom Ripley in Purple Noon.

Sadly, some of the qualities that made the OCBD distinctive and iconic then have been failing in recent times. The biggest of these is the unmistakable “S” shape formed by the collar, and that leads us to …

The Collar Roll

The OCBD’s collar roll deserves its own clutch of sonnets, for several good reasons. In the original button-down shirts, the distinctive shape of the collar roll created style and personality in the shirt all on its own. It had the power to amplify the nonchalant style of the shirt and yet served to emphasize whatever accessory was being used at the same time.

The shirts were usually made with either a soft floating interlining or none at all. This meant that the collars were pretty malleable and could get squished or crumpled easily. However, the trade-off was that they enabled the distinctive “S” shaped roll of the shirt.

William Holden wearing an oxford cloth button down shirt
William Holden
Paul Newman wearing an oxford cloth button down shirt
Paul Newman

The roll was accomplished by placing the buttons closer to the collar. So, instead of the collars buttoning down straight and flat against the shirt, they would curl up once buttoned. Hence the roll.

Today however, fewer OCBD shirts are made this way. More shirt manufacturers are using a standard, harder, collar these days. Apart from this, they are making the shirts with shorter collars, meaning there’s less room for a curl these days.

From Ivy League to Hollywood

Although it’s almost hard to believe today, the adoption of the OCBD as a mainstay of semi-casual pop culture was perfected by Ivy League students long before Hollywood caught on.

The stylish students in East Coast universities were one of the first to adopt the shirt. They created a semi-formal blasé look comprised of a preppy OCBD, tweed jackets and penny loafers which has come to be known as the “Ivy League look”. Due to the fact that the shirt can function in so many use scenarios, it became an absolute essential in students’ wardrobes everywhere.

Robert Redford wearing an oxford cloth button down shirt
Robert Redford
Fred Astaire wearing an ocbd shirt and tweed jacket
Fred Astaire

Later on, icons in Hollywood, all the way over on the West Coast noticed the style revolution going on the East Coast and bought in. Before long, these icons were stealing hearts on the golden screen in their trusty and stylish OCBDs.

Today, the OCBD has made its mark on pop culture after being a staple in Hollywood for years. Icons such as Cary Grant, Fred Astaire, Humphrey Bogart and Robert Redford all regularly sported the shirt.

Perhaps unsurprisingly, they were right on the cutting edge of what could or could not be done with the OCBD. And as we’re still discovering even till today, there’s not much you can’t do with the shirt.

How to wear an OCBD

You don’t really need a style guide to wear the OCBD. As you must have picked up by now, it can be put to use in an almost never-ending variety of functions and circumstances. Whether formal, casual, semi-formal/casual, top buttons undone, all done up, sleeves rolled up or rolled down, the OCBD just seems to fit like skin.

That said, the OCBD gained quite a reputation for being a great compromise between casual and formal. So, it’s an absolute perfect option for when you’re not sure if you’re attending a cocktail or a birthday bash.

But at the end of it all, you really determine how well your OCBD comes off, depending on how you style it. The shirt has been known to pair well with a classic navy or charcoal suit. And the OCBD paired with a pair of selvedge jeans and tweed jacket works any day or night.

Man wearing oxford cloth button down, prince of wales tweed jacket and knitted tie
Source: Gyu Chan Cho
Man wearing charcoal suit, white ocbd and gucci horsebit loafers
Source: Robert Spangle for British GQ

So… that’s a wrap

The OCBD has obviously come a long way, having been around since the 19th century. Despite this, shirt style remains relevant and in vogue, molding wonderfully to the times.

If you’d like to see what it costs to step out in this dapper shirt, check out our selection here. We have perfectly tailored OCBD’s in all the cool colors that will make them a cornerstone of your wardrobe.

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