When it comes to menswear, staid rules have long wavered and given way to methods of dressing suited to our times. However, there is one sartorial stalwart that has remained steadfast. A great oxford shirt is a necessity in any well-dressed man’s wardrobe, whether it be worn in the classic style—buttoned up and tucked into trousers—or dressed down by being worn unbuttoned over a t-shirt. While the oxford shirt never truly lost its place, its essential nature is solidified by the gradual shift away from streetwear and towards classic dressing that the menswear category is experiencing. The OCBD—short for oxford cloth button-down—has a storied history, with its roots in polo and Ivy League schools. But while its origins are distinctly old money, the oxford shirt is the ultimate style equaliser, making it easy for any man to dress well.
Our guide to oxford shirts to men details what an oxford shirt is and how it came to exist, how to style an oxford shirt (spoiler: it’s not hard), and the brands making the best ones.
What is an oxford shirt?
An oxford shirt, or oxford cloth button down, is defined by its signature basket weave fabric, wherein an equal amount of weft threads are crossed over an equal amount of warp threads. This results in a fabric that is sturdy and durable, yet soft enough to allow for mobility during sports (not that it’s worn while playing sports nowadays). The basket weave also results in a subtle yet distinguishable crosshatch texture.
Naturally, the oxford cloth button-down requires button-secured collar points, with these lending the shirt its louche collar roll. Other oxford shirt details are somewhat negotiable. A chest pocket can be handy but makes the overall appearance of the shirt more casual, while a box pleat at the back ensures a full range of motion. Pleated sleeves also lend the piece a sense of old-school charm.
While people often use the terms ‘button down shirt’ and button up shirt’ interchangeably, they are referring to two different things. A button up shirt refers to any shirt that has buttons running all the way up the front on the placket. However, the term ‘button down’ does refer to the buttons on the placket (i.e. the central opening on the shirt) of the shirt, but the ability of the collar to be buttoned down. So, an oxford cloth button-down shirt is both a button up and a button down shirt.
History of the oxford shirt
Despite its name, the oxford shirt did not, in fact, originate in Oxford, England. The oxford shirt has its roots in Scotland in the early 19th century, with oxford cloth one of four university-named fabrics, along with Harvard, Yale, and Cambridge (the latter three didn’t stick around). The nomenclature was a way for Scottish mills to add a level of prestige and elegance to their fabrics by naming them after esteemed universities.
Polo players of the British Raj were among the first to wear the oxford shirt and were responsible for its iconic button-down collar. To prevent their collars from flapping in the wind mid-match, polo players would sew buttons to the body of the shirt to keep their collars securely pinned down. In essence, the oxford cloth button-down was the precursor to what we now know as the polo shirt, despite looking vastly different to the piqué cotton polo shirts of today.
While adopted among niche circles, it wasn’t until the late 19th century that oxford cloth button-down shirts truly took off. American businessman John E. Brooks, grandson of Brooks Brothers founder Henry Sands Brooks, noticed the shirts being worn by society’s elite on a trip to the UK and began to produce his own take on the style upon return to the United States.
In 1896, Brooks Brothers released the first oxford cloth button-down shirts intended for everyday wear, dubbing it the ‘polo shirt’. The oxford cloth button-down was adopted by American Ivy League students around the 1920s, with the classic preppy all-American look pairing the shirt with penny loafers, striped or plaid blazers, and cable knit sweaters.
A few decades later, the preppy look spread outside the hallowed halls of Harvard, Yale, Stanford, and the like, becoming popular with young men wishing to align themselves with the upper-class lifestyle (see, old money style has always held a certain allure). The ubiquitous nature of the oxford shirt also saw it adopted by stylish celebrities and cultural icons like Paul Newman, Rudolph Valentino, Alain Delon, Robert Redford, John F Kennedy, and Miles Davis. The staple then made its way back to the UK, becoming popular with middle-class professionals.
What’s the difference between a dress shirt and an oxford shirt?
In the menswear world, conflating dress shirts and oxford shirts is an egregious mistake. An oxford cloth button-down shirt is a button up shirt made of oxford cloth (a sturdy basket weave fabric identifiable by its crosshatch pattern) and features collar points which can be secured (i.e. buttoned down) to the shirt. Meanwhile, a dress shirt comes without a button-down collar and is typically crafted from a fabric with a tighter weave. This can be cotton, but also cotton poplin, twill, lyocell, linen, or even silk. As they’re intended for wear in smart casual, business casual, and formal occasions and not for active or physically laborious tasks, dress shirts don’t have a box pleat at the back like OCBDs do.
From a qualitative perspective, oxford shirts age far better than dress shirts. The passage of time causes the sturdy, basket weave oxford cloth to soften and mould to the body, with older OCBDs often looking better than one straight off the hanger. An old, slightly worn—even frayed!—oxford shirt adds a louche sense of refinement to casual wear; use it as a beater and wear it while gardening, as a post-beach cover up, or around the house. It’s all very Paul Newman-esque cool without trying to be cool.
On the other hand, dress shirts don’t usually get better with time. With the exception of silk, a good dress shirt requires a certain sense of ‘crispness’ which tends to fade as the years pass. Dress shirts made from natural fibres will hold up better than their synthetic counterparts, but they’ll never compete with the worn in rakishness of a similarly aged OCBD. While an OCBD can be worn well into its twilight years, wearing an old, tatty dress shirt makes you look like a disgraced investment banker fleeing the city after a stock market crash.
How to style an oxford shirt
Bridging the gap between formal and casual, the oxford shirt has had many lives, playing an integral role in Hollywood and Ivy League circles, as well as in the Jazz Movement. With that in mind, it can be worn in several different contexts and ingratiate itself with various sartorial styles.
When it comes to styling an oxford shirt for men, it’s key to take materials and fabric weight into account. The heavyweight nature and tactile texture of a classic OCBD means it pairs well with equally durable jackets and trousers. Consider sturdy pieces like tweed or herringbone wool sports coats, corduroy trousers, pleated wool odd trousers, or flannel suits. An oxford shirt with a nubby, robust texture is one of the few button down shirt styles that can be safely paired with hardwearing denim and work within a workwear-inspired context.
The best oxford cloth button-down shirts in 2025
When it comes to price points, oxford shirts run the gamut. From affordable options ideal for buying multiples to one-and-done investment pieces, these are the best OCBDs on the market.
1. Proper Cloth American Pima Heavy Oxford
For a truly customised fit, opt for Proper Cloth’s made-to-measure service. Offering made-to-order menswear at reasonable prices, every facet of the Proper Cloth American Pima White Heavy Oxford can be customised to suit you, from the fit to the fabric and design details like the collar, cuffs, and pockets.
Price: $223AUD
2. Drake’s Cotton Oxford Cloth Button-Down Shirt
When it comes to menswear icons, visit a menswear icon. Founded in 1977 as a tie manufacturer, Drake’s underwent a change of hands in 2010 and has since cemented itself as a go-to brand for timeless menswear staples, including the OCBD. Featuring a sturdy, pronounced collar roll and a box pleat at the back, the Drake’s Cotton Oxford Cloth Button-Down Shirt epitomises the platonic ideal of OCBDs. Its hardwearing nubby cotton construction only gets better with time, slightly softening when washed.
Price: $405AUD
3. J. Crew Broken-In Oxford Shirt
As an early proponent of the humble menswear staple (with not-so-humble origins), J. Crew has a frankly ridiculous amount of OCBDs on offer at any given time. Our current favourite is the J. Crew Broken-In Oxford Shirt, which does the hard work for you, allowing you to bypass stiff and starchy beginnings and slip your arms straight into casually insouciant Ivy League territory.
4. Asket The Oxford Shirt
An OCBD that can be paired with a business suit, the Asket The Oxford Shirt is a straight fit iteration cut from soft brushed cotton with a modest collar roll and mother-of-pearl buttons. Boasting the elegant, pared-back appeal emblematic of Scandinavian pieces, it’s equally at home paired with a suit as it is with denim. Asket’s approach to sizing means that in addition to standard sizes (XS to XL), there’s the option to select short, regular, or long lengths, ensuring everyone gets the perfect fit.
Price: $200AUD
5. Uniqlo Oxford Slim Fit Long Sleeve Shirt
The best oxford cloth button down at this price point, the Uniqlo Oxford Slim Fit Long Sleeve Shirt is cut from finely textured woven cotton and has all the hallmarks of an OCBD, albiet with a slightly shorter collar roll. With a slightly slimmer fit, it takes on a sleek appearance and can be worn tucked in or left loose over a tank top or t-shirt. It comes in off-white, grey, light green, baby blue, and navy — at under $50AUD a pop, we say get all five.
Price: $49.90AUD
6. Ami de Cœur-Logo Cotton-Oxford Shirt
A more contemporary take on the OCBD. The Ami de Cœur-Logo Cotton-Oxford Shirt has a slightly shorter length and is cut close to the body; most notably, it comes without pockets which gives it a slightly more formal appearance when paired with dress trousers or suiting separates. The red Ami de Cœur logo adds a hint of edge.
Price: $520AUD
7. Alex Mill Mill Shirt
New York outfit Alex Mill nails the lived-in look, with its oxford shirt designed to feel like your favourite old shirt right from the get-go. The brand’s Mill Shirt is available in classic oxford cloth, as well as lightweight madras cloth, cotton poplin, chambray, and denim. We’re partial to the character laden madras cloth iteration for warmer weather and a the classic oxford cloth in blue or white as a daily beater.
Price: from $320AUD
8. Polo Ralph Lauren Slim Fit Oxford Shirt
You can’t mention prep without thinking of Ralph Lauren. The oxford shirt was one of the first pieces the American fashion house introduced when it was founded in 1967, going on to become a quintessential part of the ‘Ralph Lauren look’. This slim-fit iteration comes without a pocket and bears the iconic embroidered pony logo on the chest.
Price: $209AUD
9. P. Johnson Oxford Shirt
This blue and white striped oxford cloth button down by Australian tailor and clothier P. Johnson takes a relaxed approach to the classic piece. The colour palette and wide stripe evoke an elevated pyjama dressing feel. The collar roll is slightly less pronounced than ideal, however, it’s still a good casual option. The P. Johnson take is also available in other classic shades and patterns like white, light blue stripes, light brown stripes, and mid blue.
Price: $235AUD
10. Spier & Mackay Oxford Dress Shirt
Canadian brand Spier & Mackay offers solid menswear staples crafted from high-quality fabrics at an affordable price point and its oxford shirts are no exception. Designed to traverse various dress codes, the Spier & Mackay Oxford Dress Shirt is available in slim and contemporary cuts and has a cleaner appearance than a traditional OCBD, thanks to the absence of darting or pleats at the back. Fortunately, it retains hallmarks of the style like the chest pocket, allowing it to dress down a two-piece suit or feel at home with corduroys or jeans.
Price: $58USD (approx. $91AUD)
11. Brooks Brothers Stretch Regent Regular-Fit Sport Shirt
One of the original purveyors of OCDBs. While Brooks Brothers is the reason the style is as ubiquitous as it is today, its take on the staple often veers on the billowy side. However, the Brooks Brothers Stretch Regent Regular-Fit Sport Shirt has a slimmer fit than the brand’s traditional styles and comes in a wide range of checked, plaid, striped, and plain versions.
Price: $129.50AUD
12. Arket Oxford Shirt
Groundbreaking? No. Decent? Yes. Contemporary clothing brand Arket offers solid wardrobe essentials — provided you check the fabric composition. The Arket Oxford Shirt is one of the Swedish brand’s best offerings, crafted from 100% cotton with an oxford weave. The fabric is more tightly woven than traditional oxford cloth and this iteration eschews a box pleat in favour of a clean back, allowing it to be worn tucked into slim-fit suiting or pleated trousers or untucked over jeans.
Price: $69USD ($108AUD)
Enjoyed this article on oxford shirts for men? Check out our other men’s style guides here.
Words by Theo Rosen
