The Ultimate Guide To Oxford Button-Down Shirts

The Oxford cloth button-down shirt - aka the OCBD - is the glue that binds your casual wardrobe together. Here’s everything you need to know about this ever dependable and stylish garment.

With the colder weather now upon us, one garment that becomes ever important in our casualwear wardrobe is the Oxford Cloth Button-Down shirt, aka the OCBD. It’s one of those quiet, understated workhorses that is rarely glamorous but undeniably integral to our fall and winter fits.

Warm, semi-casual and perfectly preppy, the Oxford shirt comes in myriad styles and patterns, but the structure is almost always the same with the button-down collar and soft cotton flannel. As versatile as any menswear garment, the OCBD can be worn with so many different looks but where it excels is with a preppy-inspired aesthetic (as we’ll see below).

So let’s take a look at how it came to be, considerations to make when styling, and the brands producing the highest quality versions today.

The history of the Oxford shirt

Brooks Brothers Original Polo Button­-Down Oxford advertisement and current versions

Brooks Brothers Original Polo® Button­-Down Oxford

The OCBD is effectively the very first iteration of what we know as the polo shirt. Sure, it looks nothing like the piqué cotton polo shirts of today – you need to swing back to late 19th century India to find its genesis. It was there that British Army Officers found that their regular issue shirts were no good for playing polo in when off-duty, since the collar points would flap in their faces, so they came up with the idea of buttoning them down.

It wasn’t until an American businessman by the name of John E. Brooks – the grandson of Henry Sands Brooks, who founded the Brooks Brothers company in 1818 – noticed them on a business trip to the UK that the OCBD gained traction. Brooks realised these new shirts were being worn by society’s movers and shakers, and immediately began to produce his very own version when he returned to the States.

Launched in 1896, the button-down shirt was an instant hit, helped in no small part by Hollywood’s uptake of the style – messrs Gable, Astaire, Bogart, Grant and later Paul Newman were all proponents of this new casual design – before it gained traction in the Jazz movement and on Ivy League campuses.

What exactly is an OCBD?

Two Oxford cloth button-down shirts in navy and sky blue laid on bed

Asket

The ‘button-down’ bit speaks for itself, but the ‘Oxford’ bit refers to the cloth, which has a weave similar to a plain canvas with the exception that several yarns are woven in strands together, rather than individually. This gives it a very soft and comfortable handle.

Today, the OCBD is very often cut from brushed cotton or even wool flannel to give it a slight nap that feels super soft and warm. Construction-wise, the classic Oxford shirt should have a soft collar roll, and will often come with a box pleat at the back, hence it’s not particularly fitted.

How to style an Oxford shirt

After the shirt’s prominence in Hollywood and the Jazz Movement, the OCBD became an icon of Americana, not least in preppy circles. Ivy League campus students swarmed to the garment as it provided a more casual look than the starched, stiff-collar shirts their fathers wore.

With its equestrian heritage it slipped right into preppy looks, combining perfectly with relaxed sports coats, corduroy, denim, sweatshirts and chinos. Much the same today, the Oxford shirt is an excellent choice to wear with casual tailoring and smart casual pieces.

It’s also a simple way of introducing a check or stripe pattern to your look (two prominent Oxford motifs), as well as a nice textural element in the case of flannel styles.

The best men’s Oxford shirt brands

ASKET

Scandinavian brand ASKET puts sustainability at the forefront of every decision it makes, and is incredibly transparent with its production and pricing processes, which makes shopping with them an excellent experience.

Specialising in everyday staples, the button-down Oxford is a core part of its collection. Cut from brushed mid-weight 100% organic cotton Oxford cloth, milled in Portugal, ASKET’s OCBDs are an industry benchmark.

Also look at the flannel options, which are cut from a soft, brushed, custom-developed Italian twill, made using 100% organic cotton.

Shop now: ASKET

L’Estrange

London-based brand L’Estrange offers a highly curated, limited selection of ‘permanent pieces’ – i.e. staples that will never go out of style. Its self-titled ‘modular clothing system’ comprises comfortable, seasonless, versatile garments that can be mixed and matched and worn in any setting. Simplifying the male wardrobe like this means you own fewer things, make fewer decisions, and have a less overall impact on the planet.

Of course, the OCBD is central to the offering. L’Estrange calls its version ‘The All-Day Oxford’, and it might just be the most comfortable shirt you’ll ever own. Cut in a lighter weight, 146 GSM Oxford cloth sourced from Italy, it is supremely soft to the touch, has a slightly looser weave for better breathability and is blended with 2% elastane for a perfect fit that doesn’t feel restrictive.

Available in four core neutrals for ultimate versatility, this is what the Oxford shirt 2.0 looks like.

Shop now: L’Estrange

Brooks Brothers

The original and best, Brooks Brothers’ button-down shirts represent excellent value and give you that heritage cachet as the original purveyors of the style.

Naturally, Brooks has a fantastic assortment of OCBDs, with both slim and regular fits in classic Oxford cloth as well as a number of check options in a super-soft flannel, perfect for more outdoorsy looks.

Shop now: Brooks Brothers

J.Crew

The beauty of J.Crew’s website is that you can shop shirts by fabric, making finding your favourite OCBD very easy. Choose between broken-in Oxford cloth, brushed twill, corduroy and midweight flannel, then explore the many (and we mean many) colour, pattern and fit options.

You will not be disappointed.

Shop now: J.Crew

Uniqlo

The Japanese retailer of everyday essentials would be remiss if it didn’t have an eclectic range of button-down shirts, but of course it does and at an amazing price point, too.

For a fraction under £30/$30, Uniqlo offers slim- and regular-fit Oxford cloth and cotton flannel shirts in an array of easy-to-style plain colourways as well as plaid and stripe options, too.

Shop now: Uniqlo

Ralph Lauren

Oxford button-downs are an essential element of Ralph Lauren’s timeless American preppy aesthetic, so the legendary designer always delivers a superb range of OCBDs in just about every colour you can think of via his Polo label.

There is a huge amount of choice, from cotton poplin fabrics to twills and brushed styles, and a variety of fits too. Solid, classic, modern Americana.

Shop now: SSENSE

Club Monaco

Ever since it launched, Club Monaco has nailed that smart, sophisticated Euro-traveller aesthetic, focusing on elevated staples and slim silhouettes to create a well-rounded, softly tailored look that appears more expensive than it actually is.

Its button down-shirts are constructed from Oxford cotton cloth which comes from sustainable farms and represent excellent value for money.

Shop now: MR PORTER

Alex Mill

New York brand Alex Mill was founded by its namesake in 2012 with the goal of creating the perfect shirt. The brand’s no-fuss approach to making the best possible versions of menswear staples is a breath of fresh air, elevating traditional workwear pieces into something really special.

Its button-downs come in crisp Portuguese cotton, as well as corduroy and poplin, with chic stripes and bold colours featuring prominently.

Shop now: Alex Mill

GANT

GANT’s authority as an all-American preppy brand is second-to-none, and should be the first port of call for those who want the Ivy League look. With an abundance of excellent OCBD styles, including some stunning stripe and plaid options, GANT’s shirts feature a beautiful soft-roll collar.

With over 150 styles to choose from – in a multitude of fabrics including brushed cotton, twill and corduroy – if you didn’t look anywhere else we wouldn’t blame you.

Shop now: GANT

Arket

You know what you’re going to get with Arket: excellent wardrobe essentials crafted from nice organic fabrics. And so it is with its Oxford shirt, constructed from 100% soft organic cotton and available in six different colours.

At £55/$55 a pop, you can’t argue with Arket’s proposition.

Shop now: Arket

Oliver Spencer

Oliver Spencer’s unique take on relaxed tailoring guarantees that the acclaimed British designer always releases a number of button-down shirt options each season. Each comes in super-soft organic cotton fabrics, from brushed cotton and flannel cloths to textural twills and corduroy, making them some of the most comfortable on this list.

His button-down goes by the name of the ‘Brook’ shirt and features a distinct soft-rolled collar. It’s available in a wealth of seasonally-appropriate colourways.

Shop now: MATCHESFASHION

Drake’s

Drake’s, once of Clifford Street and now on Savile Row, is a master of reproducing menswear classics in the brand’s own elevated vision. Which makes them an excellent option for those looking for traditional OCBDs.

Drake’s say it best: “With a regular silhouette, floating interlinings, single-needle construction and – perhaps most importantly – an elegant rolling collar, it’s a shirt for all occasions.”

Shop now: Drake’s

Husbands

Sophisticated Parisian outfit Husbands might only create a small number of Oxford button downs, but each one is a smart iteration of the classic. Designed to be worn in a more formal manner than the traditional preppy style, Husbands’ OCBDs feature a stiffer and larger collar than normal, making them more suitable to be worn with a tie.

Using both Turkish poplin and Japanese Oxford cloth, its OCBDs would make an excellent addition to your work wardrobe.

Shop now: Husbands

Brunello Cucinelli

At the very top end of the luxury spectrum is Brunello Cucinelli whose mastery of fine fabrics extends to his button-down shirt offering. Buttery-soft fabrics are the DNA of the Italian designer, so it comes as no surprise to find that Cucinelli presents a button-down collection featuring Oxford cloth blended with lyocell, as well as pure cotton flannel, poplin and twill fabrics.

Cut in a slim fit, they easy to style with contemporary smart-casual wardrobes if you’ve got the wallet for them.

Shop now: Farfetch