The Oxford Shirt and OCBD Guide

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The Oxford Shirt or Oxford Cloth Button Down (OCBD) is an American staple that’s essential for every man. Incredibly versatile, it can be worn by men of all ages and styles. When we look back through history at the most famous style icons it doesn’t take long for a pattern to emerge. The Oxford shirt has been prominently worn by Paul Newman, James Dean and JFK. If it’s good enough for a President, it’s good enough for us.

What is an Oxford Shirt?

Unlike many other types of clothing the OCBD meaning is very clearly defined. It is constructed out of an Oxford weave, features an oversized collar with visible button-down and a middle box pleat on the back.

Most will also have a chest pocket and a barrel cuff, but these aren’t strictly required, they are merely ubiquitous. Really, the given weave and collar are the prominent features which set it apart from more formal dress shirts that could never be worn in the same manner.

Oxford Weave

This particular weave was created in a mill in Scotland, likely on the outskirts of either Glasgow or Edinburgh where the majority of mills were located. If that’s the case, why the name? The story goes that the mill named four fabric after the most prestigious universities: Cambridge, Yale, Harvard and Oxford. The other three would fade into obscurity but the Oxford cloth weave would not only survive, but thrive.

The most important feature of the OCBD, this cloth is made out of a thick cotton which was far cheaper at the time than the finer materials reserved for dress shirts. The lower price caused a boom in popularity among the middle-class, and that history combined with the rugged material makes it far more casual than a fine dress shirt.

Button-down collar

Oxford Cloth Button Down Collar

Very rarely will you find a shirt made using this cloth without a button down collar. There are two types of collar to be aware of; the classic and the modern. The classic button down collar was oversized, far longer than it needed to be, creating a ripple ’s’ shape in the collar which we have grown to love. In recent decades simplicity has taken hold, with many suppliers cutting the collar down so that it only just reaches the button.

Undoubtably the shorter collar is a more modern look, but we tend to favor the classic which is more elegant and better matches the shirt. Comparatively few brands sell these classic OCBD shirts but they are still about.

Chest Pocket

When the OCBD shirt was originally developed it featured a chest pocket. In recent years this has begun to fade away as less men have a need for them and companies attempt to cut costs. Perhaps most notably Polo Ralph Lauren, a well-loved OCBD manufacturer, replaced the chest pocket with a small logo emblem.

Barrel cuff

Casual Barrel Cuff

As with the vast majority of men’s shirts in this era, they will almost always have a barrel cuff which is the most casual type of cuff.

Middle Box Pleat

Traditionally these shirts feature a box pleat in the middle of the back which allows for extra movement. Remember, these shirts were designed for casual use and therefore needed to be practical. Some brands also include side pleats, but these are rare.

How to Wear the Oxford Shirt

While they are an absolute essential in every mans wardrobe, they aren’t appropriate for all dress codes and events. Knowing how and when to wear a button-down is vital so that you can make the most out of it without sticking out like a sore thumb. Most importantly you should recognize that it is a semi-casual piece of clothing that was designed for regular use unlike dress shirts that are best worn with a suit and tie.

White cloth shirt on hanger

Common Rules for Wearing the Oxford Shirt

Let’s be clear, you can wear whatever you want, whenever you want. But certain pieces work best in particular ways and this is no different. Following these simple rules takes the thinking out of getting dressed and will guide you towards looking dapper.

Avoid with Formal Wear

Button down collars are far too casual to be worn with formal wear such as tuxedos, morning coats and even smart business suits. Occasionally a button down shirt can work with a suit, but very rarely and only with less formal colors and cuts. To keep it simple, avoid wearing them with dress pants.

Don’t Wear it to Formal Workplaces

Many would argue that they are perfect for a business casual dress code, which we would agree with, but only in the correct workplace. A traditional corporate environment like a bank is still too formal for the button down. However, for those of us that work in less corporate offices i.e. IT roles, marketing, sales, real estate, the button down can be the ideal choice. Keep in mind the office standards and err on the side of formality.

Cary Grant in shirt

Avoid Short Sleeved Button Downs

In recent years many lower quality brands have released short sleeved button downs, which not only look odd but don’t provide the versatility that makes these shirts so desirable. Much of the time you can wear a button down with the sleeves rolled up, a fantastic look in spring, summer and even fall.

Short sleeved versions don’t have the same appeal because they have an internal clash of formality via the collar and material with a casual sleeve length. Generally, avoid short sleeved versions and opt for a traditional long sleeve shirt with a barrel cuff.

Wear Primarily for Casual and Smart Casual Events

The OCBD shines when it comes to casual and smart casual events like weekend adventures, coffee shop dates, vacations, backyard events and casual birthday parties. Here it can be worn with a variety of comfy and casual items like jeans, khakis, shorts and sweaters.

For those men who are looking to spice up their wardrobe with a touch of ‘grown-up’ and in turn throw out the t-shirts, the button down is the ideal daytime casual shirt.

OCBD with Jeans

Perhaps the most common example would be to wear it with a pair of jeans. For this outfit you need to be careful as to which jeans you choose, a casual light blue or ripped pair is likely to look out of place next to a relatively formal shirt.

Instead, most men would agree that it looks best with a tailored pair of dark jeans which are the smartest type of denim. The key to a fantastic outfit is balance, it’s okay to match casual items with more formal, but they shouldn’t be too far apart on a scale of formality, and the overall outfit should be balanced between casual and formal pieces.

With this type of shirt you should be resistant to casual jeans and sneakers because it would tip the scale too far in the favor of casual, while looking out of place next to a collared shirt. Instead, smart denim and less casual shoes such as leather dress shoes or professional Chelsea boots. These shirts go perfectly with jeans, especially when you take care for formality.

With regard to color you have plenty of freedom if you are matching to a dark denim because they are relatively plain. White, blue, navy, and pink are all tremendous choices. Most brands tend to produce shirts in a light pastel color instead of a vivid shade because it keeps it casual and makes it easier to match with different pants.

Oxford Shirt with Business Casual Blazer

While it’s advisable to avoid wearing them with a tie, in most cases, a business casual blazer can be a fantastic touch. Blazers can make jeans or even khakis more formal for work and can be quickly shedded for an evening event that is casual.

The only thing to be aware of when matching with a blazer would be the colors of each piece. White and light blue shirts tend to go great with navy and gray jackets, while pink looks better with beige and lighter colored blazers. Although it’s certainly possible to pull-off a button-down shirt with a suit, men tend to look better with a less formal pant such as khakis or smart dark jeans.

Oxford Cloth Button Down with Shorts in Summer

Always versatile, they can also be worn with shorts in the warmer months of the year. However, you need to be very careful about which style of shorts you try to pair them with. Only the smarter types will work (read: khaki shorts and not much else) in most cases.

As you might imagine, rolling up your sleeves and opening up another button or two can dress-down your formality, allowing shorts to become a more acceptable companion. This outfit can be paired wonderfully with boat shoes or even casual loafers, as we’ve seen President JFK do in the past.

James Dean and Paul Newman wearing OCBD's

The Oxford Cloth Button Down is an Essential

Truly, any man who wishes to dress elegantly and stylishly will need at least a few of these in their wardrobe. Why? Because they offer versatility, they replace more casual items that many of us have left in the past and they allow you to look great without having to think.

Many men treat these how you would a t-shirt when you were a teenager, you grab one out of your wardrobe and throw it on with whichever pants are cleanest and whatever shoes you have. More often than not you’ll look at least presentable.

They are easy and not to generalize, but millions of men value simplicity over everything else. For this reason they are essential and should be a staple of your wardrobe, perhaps even being the most common type of shirt that you have. While a dress shirt or polo is great and certainly has its applications, you’d be hard pressed to find another type of shirt that is as versatile as these. A timeless classic, it’s difficult to go wrong. Grab one in a few different colors and open up your eyes to a new era of style.

The History of the Oxford Button Down

Unsurprisingly many take a glance at them and believe that they are formal, after all, they do have a collar and a placket with buttons. But this style of button-down collar was originally invented for use by polo players who had previously worn collars that would blow in the wind during the match. Worn extensively by these players the trend spread across England where it became stylish to wear a button-down collar.

Brooks Brothers Popularizes the OCBD

American haberdashers from Brooks Brothers noticed the growing trend in the mid 1890’s on a trip to England, before taking the style back to their homeland. Brooks Brothers would release their first version in 1896, combining a button-down collar with Oxford cloth to create a casual piece that became instantly popular across the nation. To this day the company is still one of the more popular producers although in recent decades many other brands have released equal if not better versions.

The Oxford Shirt Thrives in America

At the time of release suits were still the mainstay of American men and for this reason they were almost worn exclusively with formal apparel. However, after the second World War and the subsequent relaxation of previous cultural norms, relatively casual clothing become more popular.

Rather than wearing only with suits and dress pants, it become common to wear them to attend parties, barbecues and even sporting events. Men of all age groups and demographics grabbed as many as they could because they were versatile, smart and yet casual, very affordable and incredibly durable compared to thinner dress shirts. The middle-class majority suddenly had a shirt that spoke to them, a piece for the everyday man that was available in a variety of colors and that could be worn with multiple outfits to reduce the amount of clothes they needed to purchase.

As Hollywood stars were quickly becoming nation heroes instead of just actors, cultural style icons like Fred Astaire, Paul Newman and James Dean shot into the spotlight. All three of whom would be seen in movies and magazines wearing them. Its popularity has continued to grow, or at least not decline, and today men value them as much as they have for decades before. This trend isn’t stopping anytime soon, which makes investing in at least a few quality shirts the obvious choice.

How to Buy an OCBD

Finding one to buy shouldn’t be hard at all, there are thousands of brands making them these days, but that makes it particularly difficult to decide between them. To help you we’ve listed a few of our favorites throughout this article, but we’re also going to cover what you should be looking for. Not all are made alike, and when it comes to fashion cheaper clothes are almost always going to be lower quality. Truthfully, making quality products isn’t cheap but by investing in higher quality pieces that will last you can look more stylish and save money in the long run.

White cloth shirt on man

Look for Thick Premium Cloth

Perhaps the most obvious difference between different shirts is in the thickness and the feel of the cloth. As you might imagine, inferior brands tend to produce thin material that doesn’t have the same premium look and is likely to rip or tear far quicker. One of the main advantages of this type of shirt is its durability, which is completely void if you opt for a bargain version that is going to give out within a few months at most. Instead, choose a renowned brand that uses thick premium cloth that is visibly of higher quality and will last you much longer. If you are in doubt it is fair to assume that more expensive shirts from popular brands will be superior to cheaper alternatives from unknown companies.

Don’t be Afraid to Invest

When you are looking through the different options we would implore you to resist worrying about the cost, presuming that you have that luxury. Investing in clothes is an easy way to save money in the long run because premium pieces will last far longer and because they look far better you’re more likely to continue to wear them. Rather than choosing two cheaper shirts it’s often more intelligent to choose one premium option that you will be more comfortable wearing and that will last for longer.

It’s not uncommon for men to wear them for many years and with proper care it’s not unthinkable that they could last over a decade. Considering that fact the sticker price is suddenly less important. Instead, we prefer to focus on the cost per wear. If you purchase a cheaper product you might pay less upfront but if you get less wears out of it, either because it breaks or because you don’t love it as much as you would a better alternative, the cost per wear can skyrocket. With premium clothes the sticker price is higher but they last longer and are more desirable, driving down the cost per wear significantly.

Stick to 100% Cotton Shirts

Cotton is the only material that you want, some brands offer blends that contain polyester or even spandex, and although these materials serve their purpose you won’t get the same classic look and longevity. Premium cotton used extensively to weave a thick cloth is incredibly durable and if washed carefully it won’t shrink or expand. Cotton is pricier than polyester and other fabrics, but it’s impossible to get the same feel, comfort and weight from any other material.

Pay Attention to the Collar

There are two different styles of collar, the classic oversized collar that forms an ’S’ curve, and the modern shorter collar that lays flat against the surface and only just reaches the button. Neither are better or worse, many men tend to prefer the classic collar but they are less available because of the greater cost of materials. There is very little difference between the two and while it is noticeable, experts could argue all day about whether one is more attractive than the other. If you care about the collar and achieving that classic look you should pay close attention to the photos of the product while you’re deciding between different options. The easiest way to tell is to look whether the collar lays flat or has a gap between the material and the collar.

Choose Only Long-Sleeved

Almost always long-sleeved is better than short, as we’ve mentioned previously a shorter sleeve is very casual and that will clash with the collar and formality of a buttoned placket. You can always roll up the sleeves on a hot day but it’s evidently impossible to do the opposite with a short-sleeved version. Versatility is key and that’s what the long-sleeved options offer, allowing you to get more use out of a single piece and therefore making it a more worthwhile purchase.

Keep the Colors Simple

In this day and age you can find them in every color under the sun, but most men don’t need to waste their money on such a wide selection. The vast majority of outfits look best with either a white, light blue or pink shirt. By investing heavily in these three colors i.e. two of each, you can give yourself plenty of options each day and you won’t have to constantly be washing and drying them to ensure that they are clean for the next day. Once you have found a brand that you like, don’t be afraid to stick to it and buy multiples of the same piece, plenty of guys do because it allows for simplicity while still looking stylish.


In this article we’ve covered its history, why it thrived in America, how to wear it and what you should keep in mind when you’re shopping. The Oxford shirt is an essential that every man should have in his wardrobe. It provides incredible versatility and value for money, giving you plenty of new outfit choices from a single piece. Men would be wise to find one that they like and buy a couple in a variety of colors to give themselves more choice and greater freedom so that they can wear them regularly without having to spend all their time at the ironing board.

About the author

Jack Prenter

Jack has been fascinated by fashion for decades and spent huge amounts of time researching it and becoming an expert. He's written for many well-known publications and is in the process of opening an online clothing store for men. Jack studied at the University of Nottingham and is now based out of Toronto, Canada.