The Preppy Shirts That Should Be In Every Man’s Wardrobe
Preppy devotees know that a great shirt is key to pulling off the look. Whether it’s an OCBD or soft-brushed flannel number, these button ups will slot seamlessly into any modern wardrobe and can be styled in myriad ways.
Starting in the rowing clubs of Britain’s elite universities – before crossing the Atlantic and seeding itself in the Ivy League institutions – preppy style has endured for over a century, ebbing and flowing with the cross-currents of contemporary fashion, but never disappearing. In fact, the preppy aesthetic has been one of the few menswear constants over the last hundred years, and has most recently enjoyed its place among a streetwear crossover vibe perpetuated by the likes of Aimé Leon Dore.
Preppy style has percolated through many different cultures and subcultures, and one garment has remained virtually unchanged throughout: the preppy shirt. An integral part of the movement, the preppy shirt lends a casually tailored vibe to the traditional prep aesthetic, adding collar structure and a touch of formality without any of the stuffiness of a typical ‘work’ shirt.
So let’s dig into the details to find out what exactly makes a shirt ‘preppy’, and discover which brands are getting them just right in 2023.
What defines a preppy shirt?
There are a number of factors that set apart your average shirt from a preppy shirt, the most important of which is fabric. Preppy shirts are above all casual, so there is no room for the crisp cotton poplin designs that have become the default work option worn with a suit. Instead, preppy versions are likely to be constructed from a heavier weight cotton twill, often brushed to create a soft nap effect (i.e. flannel).
The next most important distinction is the collar construction, which on a preppy shirt almost always features a soft roll rather than the stiff formality of a typical dress shirt. Smaller details such as a central box pleat in the back are also things to look out for.
Style-wise, a preppy shirt will often reference heritage sporting patterns such as stripes and checks, or will come in rich block colours.
Key types of preppy shirt
Oxford cloth button down (OCBD)
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 noticed these new shirts 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 was an instant hit, helped in no small part by Hollywood’s uptake of the shirt, with messrs Gable, Astaire, Bogart, Grant and later Paul Newman all proponents of this new casual design, before it gained traction in the Jazz movement and on Ivy League campuses.
The ‘button-down’ bit speaks for itself, but the ‘Oxford’ bit refers to the cloth, which has a weave similar to 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 often cut from brushed cotton or even wool flannel to give it a slight nap that feels super soft and warm.
Construction-wise, the OCBD should have a soft collar roll and will often come with a box pleat in the back, hence it’s not a particularly fitted design.
From the unforgiving valleys of Wales to the 90s grunge movement via the Industrial Revolution and the Great Depression, the flannel shirt has been a symbol of tough, enduring masculinity, as well as a motif for nonconformity. Today, its ‘meaning’ is benign in comparison, but it’s no less an important part of a stylish modern wardrobe, especially in the fall and winter months when it really comes into its own.
‘Flannel’ is a fairly loose term, which is why you can find flannel shirts made from cotton, wool or synthetic fibres. Essentially it describes a material that is reasonably heavy, soft and brushed on one or both sides to create an ever so slightly furry nap.
It’s believed to have originated in Wales in the 17th century, when it was usually made from a coarse wool, and was worn by farmers who needed something warm and comfortable to wear to brave the weather in the valleys. These days, 100% cotton tends to be the fibre of choice, although it can be blended with silk or man-made materials, too.
Heavier flannel, anything around 10oz and upwards, is hardy workwear, probably with a little Americana heritage. Look for an almost blanket-y feel (not fleece) and flat-felled seams, where the edges are rolled back and stitched on the underside of the shirt.
In the very early days of preppy origins, British university rowing crews used stripes to differentiate themselves from one another (as did Victorian bankers with pinstripes). Various colours and thickness of stripes were widely adopted on blazers, and this sporty trend spilled over into shirts.
Today, as then, a vertical striped shirt still has an inherent sportiness to it and is a fine way to introduce pattern to your look. Preppy styles tend to have quite thick stripes rather than pinstripes, which are more associated with the city, while horizontal motifs reference vintage rugby shirts (another cornerstone of the preppy wardrobe).
Primary colours are very much a preppy statement, ever since the 1950s when Ivy League students wore them to distinguish themselves from the boring white and pale blue work shirts worn by their fathers.
Pastel tones are another hallmark of the 2023 preppy aesthetic, so ensure you’ve got a full spectrum of tones in your wardrobe. Polo Ralph Lauren has, over the years, produced shirts in every tone under the sun and is always a great place to stock up on these classic preppy garments.
Check shirts, especially Madras checks, have always been a popular preppy look and offer a useful way to break up your outfit with pattern. Madras cotton comes from the Chennai region of India, down on the south-eastern tip of the country.
Back in the mid-19th century, British and French textile manufacturers were tripping over themselves to acquire it as it was cheaper than European cotton. This led to the East India Trading Company incentivising Indian fabric makers: if they moved to Chennai and focused all their efforts on Madras production, they would benefit from a 30-year tax exemption.
Madras caught on in the US when the Collegiate School of New Haven, Connecticut was pitching for financial donors and met a British Governor called Elihu Yale, who had made a fortune while in Chennai. He donated, among other things, large amounts of Madras cloth. In a show of their gratitude, they renamed the institution Yale University. Madras fabric couldn’t be anymore preppy if it tried.
Best preppy shirt brands
ASKET puts sustainability at the forefront of every decision it makes, and is incredibly transparent with its production and pricing processes. It’s a welcome breath of fresh air in an industry dominated by polluting fast fashion brands and opaque ‘luxury’ price tags.
Specialising in everyday staples, the button-down is a key part of the Scandinavian brand’s collections. 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, cut from a soft, brushed, custom-developed Italian twill made from 100% organic cotton.
New York label 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 playing a key part.
You tend to know what you’re going to get with Arket: excellent wardrobe essentials crafted from great organic fabrics. And so it is with its Oxford shirt, constructed using 100% soft organic cotton and available in six different colourways.
At $69/£55 a pop, you can’t argue with Arket’s preppy proposition.
Founded in Brooklyn in 2015, Adsum NYC has developed a cult following for its high-quality staples inspired by the cities and countryside of the American Northeast. Naturally, the brand has put a contemporary spin on classic flannel shirting by using bright vibrant plaid patterns for its two-button work shirts.
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.
Being the archetypical preppy clothing brand, Brooks has a fantastic assortment of button-down shirts, 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.
At the very top end of the pricing spectrum is Brunello Cucinelli whose mastery of fine fabrics extends to his luxury shirt offering. Buttery-soft materials are the DNA of the Italian designer, and 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 are all easy to style with contemporary smart casual wardrobes – if you’ve got the wallet for them.
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 sourced from sustainable farms and offer excellent value for money.
On its OCBD, 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.”
If you want a perfectly constructed, elevated version of a button-down or flannel shirt, Drake’s is peerless in choice and style.
Filson is one of those iconic brands that has left an indelible mark on the history of American workwear. Founded in Seattle in 1897, it rode the rush of gold prospectors heading north in the Klondike Gold Rush, kitting them out with the warm rugged kit needed for the bracing elements.
Then and now, heavy flannel shirts in plaid designs are Filson’s hero product. So if you’re on the hunt for outdoorsy, hard-wearing flannel, the search stops here.
GANT’s authority as an all-American brand is second-to-none, and should be the first port of call for those with a modern preppy leaning. Offering an abundance of excellent OCBD styles, including some stunning stripe and plaid options, the shirts feature a beautiful soft-roll collar.
With over 150 styles to choose from and in a multitude of fabrics including brushed cotton, twill and corduroy, if you didn’t look anywhere else we wouldn’t blame you.
As English as it sounds, Hartford is actually a French brand. Founded in Paris in 1979, Hartford specialises in traditional casual silhouettes in beautiful natural fibres, particularly flannel.
One of the cornerstones of its seasonal fall/winter collections, the label produce a wide number of flannel shirt styles – including plaids, gingham and brushed denim options – all of which will perfectly slide seamlessly into a preppy wardrobe.
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 paired with a tie.
Using both Turkish poplin and Japanese Oxford cloth, this small but beautifully formed curation of OCBDs make an excellent addition to a modern business casual wardrobe.
The beauty of J.Crew’s website is that you can shop shirts by fabric, making finding a suitable OCBD 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.
Oliver Spencer’s unique take on relaxed tailoring sees the British designer release a number of button-down and flannel shirt options each season – always in super-soft organic cotton fabrics, from brushed cotton to textural twills and corduroy.
His signature button-down goes by the name of the ‘Brook’ shirt, and features a distinct soft-rolled collar.
Fun fact: Portugal is Europe’s biggest producer and exporter of fine flannel fabric. So when a company with the name Portuguese Flannel comes along, it might be a good idea to check out its range of shirts.
Predictably, this relatively small fourth-generation, family-run outfit based in Porto does indeed produce excellent preppy flannel shirts. Each of its lightweight shirts is manufactured close to home in the north of the country, using predominantly organic and recyclable cotton fibres.
Oxford button-downs are an integral element of Ralph Lauren’s timeless American preppy aesthetic, so the legendary designer always delivers the goods with his core collection of OCBDs.
Available 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.
The Real McCoy’s
A Japanese vintage specialist, The Real McCoy’s reproduces the very best menswear silhouettes from the 1930s onwards. Its flannel shirts are always a highlight, produced under its 8 Hour Union Label in classic plaid and houndstooth patterns.
Think heavyweight flannel with rolled stitches, referencing the traditional workwear shirts of the 1950s American labourer. If you have a penchant for Americana, you’ll love its flannel options.
The Japanese retailer of everyday essentials would be remiss if it didn’t have an eclectic range of preppy shirts, but of course it does and at an amazing price point, too.
For a fraction under $40/£30, Uniqlo offers slim and regular fit Oxford cloth and cotton flannel shirts in an array of easy-to-style plain designs as well as plaid and stripe options, too.