Clean, classic, youthful and all-American, preppy clothes are usually based on popular collegiate styles from the middle of the 20th century. The look is polished but easy-wearing and when it’s done well, has a depth and attention to detail that goes way beyond the chinos-and-polo-shirt stereotype.

Prep has been around for so long that it means different things to different people. For some, it’s still about looking smart: An aesthetic symbol of the buttoned-up respectability that comes with Ivy League enrolment. For others, it’s the high-school jock stereotype—sporty, rich and endlessly popular.

Image courtesy of "Take Ivy" and T. Hayashida

Prep Through the Years

Whatever your take, with seven decades of style inspiration to draw from, preppy fashion is the easiest way to look like you’ve made an effort. Copy a Paul Newman outfit from the early 1960s—light-colored slacks and a gray marl sweatshirt is the original Newman’s Own—and you’ll still look great in the early 2020s.

The key ingredients of the Ivy League look share a mix of practicality, everyday elegance and ease of wear, popularised by brands like Gant, Polo Ralph Lauren and Brooks Brothers. There’s a sporty heritage to the look, with many styles coming from the recreational pursuits of the well-to-do, including sailing, rowing, polo and tennis.

Prep has made in-roads to designer fashion and even streetwear, but at face value, preppy style rarely wins prizes for originality. The look is classic but it’s also safe. Its roots in elite Ivy League schools and Wolf of Wall Street-types lend it connotations or money and New-England establishment, although those same perceptions have also been subverted as new style tribes and subcultures have discovered and reinvented preppy fashion over the years.

This began as early as the late-'50s, when the Japanese middle-classes began mimicking aspects of American culture. The photographer Teruyoshi Hayashida published a now-cult book called Take Ivy in 1965, which captured the way students dressed at Ivy League universities in the US.

It was hugely influential in Japan, where preppy labels began springing up in the late-’60s and ’70s, just as the style began to wane back in the States. VAN Jacket, Beams and United Arrows were among the most popular, all spurred on by energetic Japanese menswear magazines like Popeye (which is still going today). Known as ametora (a shortened version “American traditional”) it wasn’t a mirror-image of JFK’s wardrobe, but rather an interpretation of it. Some would even call it an improvement.

The Japanese take features more texture, wider cuts and more denim, with elements of blue-collar workwear blending seamlessly with tweed sports coats and Oxford shirts. Today, the look is best exemplified by labels like Beams Plus and Warehouse & Co.

It wasn’t just overseas that the preppy style evolved, however. In 1980, another hugely influential book was published, this time in the States. The Official Preppy Handbook, edited by Lisa Birnbach, was a satirical guide to all aspects of life as an upper-middle-class prep—fashion included. What was intended to gently parody the preppy subculture actually expanded it to the masses.

The book’s massive success is said to have influenced the founding of J.Crew and revived the fortunes of L.L. Bean. Preppy fashion went from being something privileged and exclusive to what you’d see at the mall; with that mass take-up came a poppier take on the aesthetic. Logos became bigger, the colors bolder. Preppy became the unofficial uniform of hundreds of 1980s high-school comedies.

From there, it evolved again. Emerging brands like Tommy Hilfiger shrewdly marketed their collections to the MTV generation with music and other aspects of pop culture. Hip-hop took notice. By the late-1990s and early-2000s, fashion icons like Kanye West were expanding on the idea of prep, bringing the once exclusionary aesthetic into the mainstream, tapping into brighter colors and over-the-top styling to remix the look.

Now, as designers revisit 1990s fashion in all its forms, preppy is being reappraised again. From the conceptual and luxe vibe of Thom Browne to the tradition-with-a-wink at Rowing Blazers, the preppy look is still evolving, still interesting, still more than worthy of your attention.

Today, rapper/artist/style icon Tyler, the Creator has spun up his own iteration of prep style, mixing modern streetwear aesthetics, with a early-2000s candy color palette into a contemporary take on the prep style. The collaboration between his own label Golf le Fleur* and Lacoste for faithful throwbacks to 1980s-style polo shirts and 1950s-style varsity jackets.

Polo Shirt

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.

Varsity Jacket

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.

Chinos

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)

Rugby Shirt

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.

Blazer

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.

Penny Loafers

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.

Founded by Charles Alden in 1884, Alden represents a haven of prep style—New England—within the wider menswear landscape. With a focus on luxury and last over price, Alden kept production in America. Tapping into the classic Goodyear welt—notorious for keeping shoes secure and relatively waterproof—the Alden shoe is reliable, albeit a bit bulky.

With little information available from the brand directly online, it can be a little confusing to know what exactly to buy from the Alden brand (and, more importantly, how the footwear fits). From its signature 405 “Indy Boot” Workboot (nicknamed as such after appearing on the feet of Harrison Ford in Indiana Jones), to the Leisure Handsewn Loafer (in 986 burgundy cordovan leather, natch), it doesn’t get more “Ivy” than Alden.

The poster brand for Japan’s love affair with Americana, Beams started as a small shop modeled on a UCLA dorm room in Tokyo’s Harajuku in 1976. Today, it’s grown to become a sprawling retail empire that is far better known on home soil than abroad.

Beams itself remains the anchor, a collection of considered, endlessly wearable clothes that still pays faithful tribute to American preppy staples. Sister label Beams Plus is arguably more coveted, founded in 1999 to double-down on the stable’s preppy roots but blending them with an interesting mix of sportswear and workwear. And the quality is emblematic of Japan’s reputation for world-beating craftsmanship.

In many ways, Brooks Brothers is the grandaddy of American menswear, and certainly one of the oldest brands still producing clothes today. Founded in 1818, it claims an impressive number of menswear firsts, including ready-to-wear suits, Madras shirts and oxford shirts. Some will think its designs are stuffy and inaccessibly priced, but the truth is that this 200-year-old label has done more to democratize fashion than most others. If you want authentic preppy staples with centuries of heritage, start with its excellent navy sport coats.

“Relaxed elegance” is the modus operandi at Drake’s, which is a fitting tagline for the entire preppy movement. A British brand, it began life in the 1970s selling scarves and shawls. The pops of color that made them popular survive to this day in the brand’s full range, which mixes button-downs and polos with tailored chore jackets and great denim.

Its shirts are particularly good, all handcrafted in the label’s own factory, although a smart string of collabs are even more sought-after. Recent highlights include Aimé Leon Dore and Fred Perry.

It’s headquartered in Sweden today but Gant helped to shape the Ivy League look in its hometown of New Haven, Connecticut. Originally a shirtmaker with a store close to the Yale University campus, its colorful oxford shirts were popular with 1950s students. It wasn’t until the late-’60s that a broader range of clothes was added, with rugby shirts, ties and trousers reflecting the broader preppy look.

Today, the label leans hard into its collegiate past, with letterman jackets, hoodies and sweaters all on the roster.

For a British take on preppy style, Hackett scans a little something like Polo Ralph Lauren with a Hugh Grant accent. Just as the American preppy brands reference Ivy League schools, the big influences at Hackett are Oxford and Cambridge with their rowing clubs, rugby teams and old-school British tailoring.

In 2019, the brand set up shop on London’s famous Savile Row—where it offers personal tailoring—but Hackett is at its best doing a gentlemanly take on smart-casual. Think tailored separates, luxurious polos and padded gilets.

With roots in catalogue-order fashion stretching back to the middle of the 20th century, J.Crew as we know it today began in 1983. Cruel commentators might describe it as cut-rate Ralph Lauren, selling as it does many of the same New England staples, from oxford shirts and chinos to dock shorts and rugby jerseys. But that fails to acknowledge J.Crew’s role in shaping and popularising the look in the ’80s and ’90s.

In recent years, J.Crew even managed to steal some of the exclusivity more often associated with streetwear’s drop culture. It sells limited edition sneakers in exclusive deals with the biggest brands—Nike’s perma-hyped Killshot 2 being the best example.

It may not be as ubiquitous as it once was, but to ignore J. Press is to ignore a crucial part of preppy style history. Founded by Jacobi Press in 1902 on Yale’s campus in Connecticut, it became practically standard issue for incoming freshmen to pick up a J. Press suit as they were coming into on-campus life. Throughout the early and mid-1900s, the clothier would fluctuate between outfitting students and soldiers; when one-time students would be drafted into wartime service, it was entirely possible that they’d be trading in a J. Press sportcoat for an J. Press officer’s uniform. By the 1970s, the burgeoning Ivy movement (as documented in Take Ivy) spurred Japanese interest in J. Press; after a deal is coordinated with Onward Kashiyama, J. Press becomes the “first classic American menswear brand to license in Japan”—according to J. Press.

While J. Press stocks plenty of its own top-tier Ivy League favorites, the Shaggy Dog—a furry, Scottish-made wool sweater, remains a cult favorite no matter how committed you are to the prep lifestyle. With a cacophony of color options, you’d be hard pressed not to find one worth investing in.

Based in Freeport, Maine, L.L. Bean is an unassuming and—dare we say it—proudly un*fashionable part of the preppy firmament (it was founded in 1912). More outdoorsy than most Ivy League-style labels, it nevertheless sells lots of quintessential chinos and plaid shirts. Don’t let that sully its credibility; in *The Official Preppy Handbook, Lisa Birnbach describes the brand’s Norwegian pullover as “the nearest thing to a preppy membership card.” The brand’s aptly named “Bean Boots” (its sell-out, time-tested duck boots) are a cult favorite among prep fans and the regular populace alike.

Now the brand is getting some overdue attention from more mainstream fashion. A 40-piece capsule collection with New York sportswear stalwart Todd Snyder is scheduled for the Fall/Winter 2020 season.

Preppy is a style firmly rooted in the past, so it takes a particular kind of person to take it into the future. That person might be the former creative director of Supreme. The collection at Brendon Babenzian’s youthful label Noah mixes traditional preppy items with skatewear and elements of punk fashion, albeit in looser fits and with bolder colors, graphics and patterns than you’d have ever found on campus in 1965.

You might find a double-breasted sport coat in leopard print, or woollen varsity jacket in Barbie pink, or a string of sailing and surf inspired streetwear. As one of the best brands currently operating in NYC, Noah’s unique approach to design and branding have turned it from cult favorite to must-cop in a very short period of time—with or without its connection to Supreme’s family tree.

The Ralph Lauren Corporation is today a sprawling family of sub-labels, most of which lean preppy, but it all started with the first full line of Polo Ralph Lauren in 1968. The man behind it all had worked at Brooks Brothers and sold a line of ties before branching out and securing an exclusive coffering at Bloomingdales. The famous polo shirt followed, emblazoned with the iconic motif of a polo player on horseback.

That same logo found its way onto tees, oxford shirts and sweatshirts, and as the brand grew into a powerhouse of cool Americana, more iconography followed: the playful Polo Bear—itself now a streetwear icon—and the American flag itself, woven into crew-neck sweaters. The latter is perhaps the most fitting emblem for the label which, 50 years on, is as close as they come to fashion’s embodiment of the American Dream. If you can find anything from its 2018 collaboration with Palace Skateboards, you’ll see why it’s gone the distance.

It was only founded in 2017, but Rowing Blazers is a label that’s steeped in heritage and, at the same time, completely modernizing the preppy look. Founder Jack Carlson, a former US rower, wrote a coffee-table book while studying at Oxford. The focus? The history of the colorful blazers worn by oarsmen at rowing clubs everywhere.

Later, the passion spilled over into his own clothing brand, which makes incredibly faithful versions of most preppy classics, not just blazers. More than that, it imbues them with a playful and eclectic style that draws in streetwear, hip-hop culture and other influences. With collaborations with prep icons like Barbour and Beams Plus sitting alongside work with Noah and New York’s Nom Wah Tea Parlor, Rowing Blazers is an ironic and colorful rebuke to anyone who thinks preppy has to mean stuffy.

Founded in 1985, at the height of the second wave of all-American prep, Tommy Hilfiger’s eponymous brand launched with modernised versions of preppy staples like, polo shirts, button-downs, cardigans and windbreakers—all in poppy primary colors. The red-white-and-blue aesthetic is still prevalent in Tommy collections today, but the brand has been more adaptable than many of its preppy stablemates in embracing shifting fashion trends.

Its baggier fits and big logos earned the brand a place within hip-hop culture in the 1990s, and recent collections have fondly and faithfully revisited that heyday. Back-to-back collabs with Kith prove that its streetwear credentials are still strong 25 years later.