In the late 1800s and early-1900s, sportswear wasn't very sporty at all. Polo players wore button-down oxford shirts and
tennis players ran around the court in button-up dress shirts and a tie. The solution to both cumbersome dress codes was what we now call the polo shirt, a short sleeved tee, traditionally made from pique-weave cotton, with three buttons on a placket neckline and a turn-up collar to protect the wearer's neck from the sun.
The popularity of these sports at prestigious universities meant the garment became a cornerstone of the preppy look. Even today, the quintessential polos are still made by Lacoste (whose founder was the first to wear one on the tennis court) and
Polo Ralph Lauren, whose iconic breast design didn't come about until 1972, but defined the preppy look in the 1980s and beyond.
Polo shirts are available in virtually every color imaginable, but bold and pastel colors hark back to the ’80s version of prep. To find a more modern take, with a boxier cut and muted colors, try
Engineered Garments x Uniqlo.
Sometimes confused with a bomber jacket, this preppy classic features a similar collarless design with an elasticated hem at the waist, but there are key features to look out for. In the most traditional iterations, the body should be woollen and the arms leather (or leather-ette) and there should be no zip at the front, but buttons instead.
Classical styles feature a large embroidered letter on the chest. Known as a letterman jacket, this design dates back to the mid-1800s, when Harvard gave members of its sports teams sweaters with a large ‘H’ on them.
The style is synonymous with onscreen high-school jocks, but has also found favor in hip-hop in recent years. As well as preppy brands like Gant and Polo Ralph Lauren, check out specialists like Golden Bear or sports-lifestyle labels like Champion with a history of track-and-field fashion. Even Virgil Abloh’s Louis Vuitton has tapped into the style, tweaking the jacket to accommodate one of
his earlier collection’s . Wizard of Oz theme
Cable Knit Sweater
The origins of cable-knit sweaters lie in small Irish fishing villages of the 1800s but they became a mainstay of the mid-century preppy look via jumpers worn in cricket, tennis and other sports associated with well-to-do schools. To be fair, it’s a practical student student purchase: warm, hard-wearing and weather resistant. The fact that a fine-gauge version looks great under a sportcoat is just a bonus.
Away from the collegiate crowd, cable-knits were being worn by Elvis Presley and
Steve McQueen, cementing their timeless wearability. It’s such a classic style that everyone from Burberry to Banana Republic has a cable-knit somewhere in its fall collections. Check out mid-weight options from Japanese label Beams Plus. Classical styles—in the Irish tradition—can be found over at Inis Meain.
Oxford Cloth Button-Down Shirt
In 1896, one of the
founding fathers of preppy style, John E. Brooks of Brooks Brothers, noticed that English polo players pinned their collars down to stop them flapping in the wind. He liked it. Brooks soon created a shirt that used a button to do the same job (and confusingly, he called it the polo shirt).
We know it as the oxford shirt today because of the cotton used: a distinctive basket weave texture that gives the shirts a softness that you don’t get with many dress shirts. It found popularity on the campus but also beyond. Miles Davis wore one on the cover of
Milestones in 1958. The Rat Pack wore theirs with the top button undone and the ties loose. Ralph Lauren wore one everywhere.
It’s another everyman icon of the preppy aesthetic and there’s probably one or more hanging in your wardrobe already.
After World War II,
returning GIs continued wearing flat-fronted trousers at home and the style soon caught on at Ivy League schools, in Hollywood and most places in between. The style’s military history means they are usually made from a slightly heavy twill cotton which, in turn, is what made them the ultimate smart-casual trouser. Dress-down Fridays wouldn’t be possible without them.
In the cartoonish stereotype of preppy style, the chinos are usually red, but today they’re mostly worn in neutral colors like stone and navy. Outside of the hype cycle, it’s a style that moves with broader fashion. Slim and skinny fits were popular five or 10 years ago, but we’re now seeing boxier cuts come through as wider silhouettes take priority. This gives rise to the traditional chino—either in a workwear context (see
Dickies’ signature 874 pant)
The rugby shirt as a fashion piece offers yet more proof that the Ivy League look borrows heavily from sports enjoyed by the upper classes of the first half of the 20th century. Essentially a thicker version of a polo shirt with long sleeves, colorful horizontal stripes and contrast collars, you could wear one with chinos or under a sports coat.
The style has enjoyed a renaissance in recent years, embraced by skatewear and hip-hop labels—especially Noah or Palace—as well as traditionalists like J.Crew or Rowing Blazers.
Blazers and sport coats form a cornerstone of the preppy look with traditional rowing styles, shooting jackets and nautical navy styles all contributing to the aesthetic. Usually worn with chinos in a different color, they’re dressed up with a button-down shirt and (optional) tie, or kept causal with a polo shirt, tee or crewneck sweater.
Gingham, seersucker and plaid styles are among the most resistant styles to wider changes in fashion and modern cuts with minimal padding and structure ensure they look contemporary.
You’ll also find boat shoes and canvas sneakers in any self-respecting prep’s foot locker but
penny loafers are really the quintessential preppy shoe style. G.H. Bass created its first pair of Weejuns in 1934, paying tribute to a style of loafer first made by Norwegian shoemaker Nils Gregoriussen Tveranger. It had a strip of leather across the upper with a diamond-shaped cut-out feature just big enough to hold a coin (hence the name penny).
The style really hasn’t changed much in the decades since. It’s the preferred choice of preps because it’s smart but also comes with a dash of insouciance that means you can wear them with cotton shorts just as easily as with a smart pair of trousers.
As well as G.H. Bass, check out
Tod’s and Trickers for some of the best loafers.