It would be remiss of me to begin a study on preppy fashion—its origins, ever-changing façade and enduring legacy—without setting the scene. In London, where I write this and where some of this story takes place, prep is everywhere. And whilst the prevalence of preppy fashion is what could make the trend seem common, it’s actually its association with the Sloane Rangers and "Rahs" that serve as prototypes for this aesthetic—and their upper-class exclusivity—that has made the trend thrive.
British novelist George Orwell once wrote in a 1946 essay that "England is the most class-ridden country under the sun. It is a land of snobbery and privilege." Unflattering as that observation may be, and whether you agree with it or not, it should come as no surprise that the institutions and establishments deemed to uphold these values are a hotbed for promoting this way of dressing. If you pay attention, you’ll begin to notice that preppy fashion actually is all around us. It’s verbalised in the way penny loafers trot over the lanolin floors of offices, or the way blazers glide throughout city streets, even if the wearer is off-duty.
In the British Library, however, a hallowed ground where preppy fashion should seemingly be expressed in its truest form, those working in the space aren’t wearing clothes you’d typically associate with these conventionally elite settings. In a bit of gonzo journalism, I observed that traditionally preppy pieces like argyle patterns and cable-knit jumpers weren’t favoured by this set. Instead, casual jeans, relaxed suede jackets, simple collared button-downs and even on-trend trainers were the preferred items. So, if prim chinos are being worn to the pub and minidresses are being worn to study, what exactly does preppy fashion look like today?
Left to right: Norma Kamali's spring 1983 collection, Cindy Crawford modelling Ralph Lauren's spring/summer 1989 collection, members of the U.S. Olympic team chatting at Henley-on-Thames in England during the rowing event in the 1948 Summer Olympics, students at Lincoln University in 1984 and a student fashion show atClaflin University in 1960.
Thankfully, there’s a handbook for that. Published in 1980, The Official Preppy Handbook serves as a compendium for navigating this conundrum. From choosing the most suitable nickname to debunking the politics of monogramming, this manual outlines how to achieve prepdom with an "abundance of detail," as spelt out in the foreword.
Speaking to The Official Preppy Handbook's editor and co-writer, Lisa Birnbach, who is somewhat of a prophetic figure in these circles, I learn that the definition of preppy fashion has remained somewhat unchanged over the 45 years since it first became marketable. Now in her late 60s, Birnbach has witnessed every iteration of preppy fashion: the minimalist expression of the '90s, the sleazy version of the 2000s, the 2010s twee take and the luxury approach that’s prominent now. However, as she argues, preppy fashion in its most authentic form is not too dissimilar from the fashions she saw and wore herself as the nascent 21-year-old who penned the handbook.
"Preppy fashion is a British-originated expression of classic clothes in which the wearer feels comfortable," Birnbach explains over Zoom. “It does not need to be a certain size or shape, can be unisex and doesn’t need to be very flattering," she adds. "When you get dressed in preppy clothes—your cotton trousers, your cardigan—you are dressed for anything and everything. The joke in the Preppy Handbook was that whatever you wear in the morning can take you to a sporting event and could also take you to cocktails."
Left to right: Alicia Silverstone and Stacey Dash in Clueless, Blake Lively in Gossip Girl, Reese Witherspoon in Legally Blonde.
Professor Carolyn Mair, PhD, a fashion historian and author of The Psychology of Fashion, echoes this statement. "Preppy fashion began in the early 20th century, rooted in the Ivy League university aesthetic," she says. "Initially a reflection of upper-class leisurewear, it evolved into a broader aspirational style which endures because it offers a timeless, structured identity."
For those who grew up in the early 2000s like me, our resource for understanding and obtaining preppy fashion was an entirely different format altogether. Instead of a 200-something-page guide, shows like Gossip Girl were our bible. In the way a character like Serena Van Der Woodsen mixed her Constance Billard uniform with designer pieces, it was inferred that preppy fashion was first and foremost collegiate, but also reserved for those with privilege. But as Birnbach tells me, real preppy fashion couldn’t be further from this preconception.
"My daughters went to the school which Gossip Girl was based on," Birnbach says. "The clothing on this show was tarted up for TV; you could not get away with wearing your uniform skirt so short that it was basically the width of a belt!" I tell her about a moment from the show’s second season where Blair Waldorf criticises one of her wannabes for wearing last season's Tory Burch Reva ballet flats. As an impressionable teen, this cemented to me that preppy fashion was mutually exclusive with a sort of condescending arrogance that accompanied those who attended fee-paying schools. "That's excellent," she says of the show’s writing. "Nearly everyone at my kids' school wore them, but the idea that you would talk about them is not preppy. To be preppy would be just to wear them."
Jacob Elordi in 2023's Saltburn. Sophie Canale designed the costumes for the BAFTA-nominated film, winning the Excellence in Contemporary Film prize at the Costume Designers Guild Awards.
Of course, here in Britain, these wealth-expressing signifiers are slightly more inconspicuous anyway. Sophie Canale, an award-winning costume designer, acknowledges this firsthand through her fashion choices in Emerald Fennel’s psychological and sycophantic black comedy Saltburn. Both Barry Keoghan’s Oliver Quick and Jacob Elordi’s Felix Catton approach preppy fashion in different ways, as pre-determined by their socioeconomic standings.
"When I was fitting [Elordi], the cut of the jeans was important, as well as the bigger Ralph Lauren shirts and popping the collars on the polos," Canale says of these small details that would signify him as in the know. "There’s a preppiness to it, but it was also styled in a street fashion sense as well. It's this combination that pulled the prep look into this kind of sportswear feel to make it more contemporary," she adds.
As the film was set in 2007, it was vital to mark this decade as a key turning point in prep fashion. Instead of being prim and polished, it was more savvy for shapes to be more billowing, unfussy and treated with a certain disregard. To translate this indifference to the screen, Canale looked to the society pages from the time.
Left to right: Prince Harry at the Beaufort Polo Club, Gloucestershire in 2001, Prince William in St Salvator's quad at St. Andrew's University in 2004, Prince Harry at the Prince's Polo event at Royal Berkshire in 2003.
"I was looking at who the It crowd was at that time," Canale elaborates. "Because the structure of Saltburn is about the class system in the UK, I was looking at Prince Harry and Prince William in that period. I drew from royalty and their friendship groups when they were out in London, but also looked at that world of polo matches and moving out to university, as well."
This historical accuracy obviously contributed to the film’s box-office success. More significantly, it gave preppy fashion cultural cachet again. At the turn of the 2020s, the aesthetic was given a high-fashion makeover, courtesy of Miu Miu’s spring/summer 2022 collection. With one viral miniskirt—cut with a raw hem at microscopic proportions—cardinal preppy silhouettes were revived and re-examined through a designer lens.
At Louis Vuitton, striped rugby jerseys were updated to suit the streets of Paris, rather than a football field, whilst Coach took a more youthful approach, offering playful argyle jumpers and silk dresses that looked like they were ripped from Donna Tartt’s The Secret History.
Left to right: Miu Miu autumn/winter 2022, Celine spring 2026, Balenciaga spring/summer 2025, Miu Miu spring/summer 2022, Coach resort 2025, Louis Vuitton autumn/winter 2022.
For one of his final collections for Balenciaga, Demna took an outfit nearly identical to one worn by Elordi in Saltburn and put his own ironic twist on it. Instead of a polo shirt emblazoned with the Tommy Hilfiger logo or teamed with colourful rubber bracelets and Wayfarers, the ensemble featured a striped version with chunky trainers and wrap-around sunglasses, and was modelled by Romeo Beckham.
Yet, in 2025, you don’t need an Eton education or access to Annabel's, a private member's club in Mayfair, to dress in preppy fashion. Yes, there are designer offerings if you have the means, but there are plenty of just as suitable options on the high street, too. As Birnbach puts it, "the higher the price you pay, in a way, the less preppy it is, because it's making more of an effort."
"The misunderstanding of preppy culture is that it’s all about money. Some of the preppiest people I know are also the biggest 'moochers' I know, wearing threadbare hand-me-downs. It was never about money. It was about good manners, athleticism, charm and a kind of insouciance."
A look from Kent&Curwen's autumn/winter 2025 collection.
"These days, you could buy an entire preppy wardrobe that took someone 40 years to assemble in one day. If you were so motivated, you could buy your charm bracelet pre-made, for example," she adds. "When someone like Gigi Hadid makes a polo shirt with her knitwear company [Guest In Residence], is that preppy? Well, its roots are. Even if the wearer doesn’t, for instance, know anything about the sport or the academic background, or isn’t well-read or doesn’t know who T.S. Elliot is. Those [associations] are still there."
Indeed, we can’t ignore the context from which they originate, which is to say, from exclusive pursuits and pastimes, irrespective of whether we shop preppy at luxurious or frugal price points. "Preppy fashion has always had this fascination with upper society," Canale notes. To Matthew Longcore, a Yale graduate and creator of The Official Preppy Handbook fan club, fashion’s fixation with preppy clothing comes down to one thing. "We live in an aspirational world. So many of us have a bit of Jay Gatsby in us. In reality, we don’t automatically experience upward mobility through nice clothing, but it always helps to be well-dressed."
Birnbach agrees. "If I recall correctly, one of the first sentences of The Official Preppy Handbook is, 'In a true democracy, everyone can be upper class.' So the idea, even then, was to open up the doors to a mildly secretive world. I thought seven people who went to Exeter or Andover and then went on to Princeton would read the book when it came out, and that I’d be looking for a job writing something else. The [goal] was to help people look like [they] had the breeding, the money, the education and so on."
Left to right: Little Simz at a Miu Miu event during the 77th Cannes Film Festival in 2024, Hailey Bieber in 2023, Shay Mitchell at Tommy Hilfiger's spring/summer 2025 show, Taylor Swift wearing Stella McCartney in 2023, Rihanna wearing a Loewe striped polo sweater in 2023.
In a modern context, prep fashion is less about conveying the latter. Still, the sentiments and associations remain. In my own wardrobe, a pair of suede boat shoes has become a part of my office attire. Does that make them preppy, if they're worn outside of a yachting environment or with something less cohesive than Tommy Hilfiger’s collaboration with the U.S. SailGP team? Well, the look certainly gets Canale’s tick of approval. "I'm from a very small sailing town. Boat shoes are preppy. It comes with those hobbies and the sets of people who have them, but then, within the context of 'everyday' people, [they're] such an easy piece."
"I've seen hipsters wearing boat shoes in Brooklyn, and they think they invented boating. The irony of it!" Birnbach laughs. Of course, on a more mainstream level, this even comes across through the off-duty looks of the celebrity style set. Hailey Bieber certainly isn’t running to class when she wears a V-neck knit with loafers. Yet, this gravitational pull towards preppy fashion is so undeniable simply because of how effortless the aesthetic is.
Birnbach has made a vocation out of advocating for preppy fashion, having been drawn towards it in the first place for its simplicity. As someone with a self-proclaimed lack of fashion imagination, the "goes with everything" sentiment is what’s kept her wearing prepped-up clothing for her entire life, she tells me. As she puts it, prep has never fallen out of style. "Part of the pleasure of preppy dressing is that you accumulate over time and with some care," she says before stringently adding, "not too much care, of course, just the right amount."
However, I’d contend that prep has never been more pertinent. From the rise of celebrity book-based communities like Kaia Gerber’s Library Science, to the rise of reading events like Miu Miu’s Literary Club and even our collective fixation around cultivating a personal uniform, the remnants of preppy fashion are far-reaching. And if the clothes you wear signal a sort of erudite attitude—one that conveys a scholarly aptitude and well-travelled life—is there anything inherently wrong with that? Or, are we just all Tom Ripleys in a world of Dickie Greenleafs?
French fashion influencer @emmanuellek_ at Miu Miu's Summer Reads event at the Bibliothèque Nationale de France in Paris.
"Preppy fashion’s core appeal is the performance of knowledge, taste and social capital. It communicates values like tradition, intellect and affluence through visual cues, often regardless of the wearer’s actual background," Mair explains. Birnbach has a different take. "They’re just easy clothes," she asserts. If you’re wearing a cashmere jumper (a bona fide preppy fashion staple) through Central London, no one is going to give you a second look. "You will not be noticed. You are in camouflage," Birnbach says of the power of preppy fashion.
"It obviously depends where you go, what your life is, who your mates are, but the fact is that you can live under the radar in these clothes." But with so many misconceptions surrounding it, and no one to really gatekeep the preppy fashion credo, does preppy fashion run the risk of becoming obsolete? I don’t have a crystal ball; still, with an elusive and ever-changing expression, I predict we won’t see the end of it.
"Preppy fashion will always be here, and how chic it is depends on whether [designers] continue to make fashionable versions of unaffordable clothing that everybody wants," Birnbach muses. The important thing to remember is that to be truly prep is to make these pieces your own. "For those of us who appreciate a nicely-made, long-wearing garment, it will always be part of our wardrobe, whether you pair it with something [else] preppy or not."
In every expression, preppy fashion arms you with the ability to move through the world however you see fit. So whether you’re working from a Covent Garden cafe, strolling through campus or pounding away at the keys of your laptop from a King’s Cross reading room, all you need to do is go out and live in it.
The Best Preppy Fashion Items to Shop in 2025
To start you off, I’ve compiled an edit of the key pieces to help you curate an effortless preppy capsule wardrobe.
1. Argyle Prints
Style Notes: After staging its comeback at Miu Miu’s A/W 22 runway show—a presentation that continued the brand’s fascination with collegiate uniforms but with a sportier tone—argyle has been unrelenting. Play your cards right and you’ll get a look that’s equally abundant in charm, albeit with a little kitsch twist.
2. Pleated Skirts
Style Notes: Like how Jenny Humphrey took a torch to her prim school regalia in Gossip Girl, ditch more matronly pencil cuts and midi lengths for a pleated miniskirt with plenty of swish. (Bonus points if you invest in a Prince of Wales check or classic tartan.)
3. Penny Loafers
Style Notes: From Saint Laurent to The Row, this staple of '80s "yuppie" culture is no longer the preserve of the trading room floors of Wall Street or corporate offices. In fact, if you look further uptown, you’ll notice a flurry of stylish dressers, including Zoë Kravitz and Kendall Jenner, running around Manhattan in this sleek flat-shoe style. You know what they say: find a penny, pick it up…
4. Tailored Trousers
Style Notes: Prep might be laden with a typically boyish sensibility, but tailored trousers are a hallmark that has swiftly been reclaimed as neutral ground. These are nothing like the scratchy pairs you wore in Sixth Form. Instead, think tapered at the waist and with a structured pleat through the middle to provide a clean-cut silhouette.
5. Boat Shoes
Style Notes: A pillar of the "yachtie" aesthetic, this sturdy shoe has traded its former frat-boy associations and maritime environments for the street style set. Yes, designer endorsements have certainly helped this shoe garner a reputation for effortless elegance, but the high street excels at affordable, expensive-looking options.
6. Polo Shirts
Style Notes: Thanks to a renaissance attributed to Y2K nostalgia, a runway rendering from the now-defunct Copenhagen cool-girl label Saks Potts and, obviously, Saltburn, polo shirts are being snapped up with more fervour than we've ever seen before. Sure, you might not know how to swing a mallet whilst riding a horse, but you'll certainly look good.
7. Boxy Blazers
Style Notes: From Winona Ryder in Heathers to Alicia Silverstone in Clueless, blazers are a style stitched with all the airs and graces associated with preppy fashion since the aesthetic was coined. Still, when dressed down with denim or thrown over a pair of slouchy pants, the overall silhouette is undoubtedly cool in an undone elegant sort of way.
8. Ballet Flats
Style Notes: Away from dance studios and grand theatres, ballet flats have always been synonymous with preppy fashion. When worn with tights, they evoke an air of smug chicness and coquettish allure that's just so unique to the trend. It's a truly en pointe pairing.
9. Button-Down Shirts
Style Notes: A button-down shirt is inextricably linked with classroom attire. Still, there's something so captivating about this fundamental piece. Though true preppies will always keep theirs oversized—Birnbach explains that boxy cuts that conceal the body are preferred by this cohort—a sultry colour or silky fabric can go a long way. Class truly is in session.
