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Trend Report: The New Preppy
Preppy style used to be a hushed transatlantic conversation between the monied classes of Britain and America. It’s becoming a menswear mega-trend that can be seen and heard around the world. With prime movers continuing to loosen up the Ivy League look for 2025, we had to investigate…
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Where Has It Come From?
The name ‘preppy’ relates to the private schools in America that ‘prepared’ rich kids for college (or the ‘Ivy League’, another name by which the style is also known). According to style podcaster Avery Trufelman, the word was “catapulted into the public consciousness” by the 1970 film Love Story “in which Ali McGraw teases her old-money boyfriend by calling him ‘preppy’.”
But the style predates its naming. The original preppy aesthetic revolved around mid-century leisure pursuits and the strict social mores of the country or sports club – think polo, boat racing, golf, tennis, lacrosse and the society folk lounging nearby. Sartorially, this presented as polo shirts, seersucker, rugby shirts, Wayfarers, varsity jackets, khakis, linens, cricket jumpers, boat shoes, chinos, madras, gilets, oxford shirts and penny loafers.
Powered by all-American brands like J Crew, LL Bean, Brooks Brothers, Perry Ellis and Polo Ralph Lauren, preppy peaked again in the 80s and 90s. Away from the country clubs, though, Black Americans such as Amiri Baraka, Charles White, Malcolm X, Martin Luther King Jr, James Baldwin, Miles Davis, John Coltrane and Sidney Poitier had been subverting and claiming preppy style for themselves. This parallel tradition is documented by Jason Jules in Black Ivy: A Revolt In Style, and the men who drove it were among the first to release preppy style from its buttoned-up origins.
What’s Going On Now?
Preppy is being rejuvenated by growing lethargy towards sneaker culture, wider access to quality vintage shopping via Depop, Vinted and eBay, and the social media trend of ‘dressing like your grandad’. TV and film seem equally obsessed with the monied classes – look at how Saltburn, Succession and The White Lotus have each gripped the cultural milieu on release. Last summer’s tenniscore trend – fuelled by Challengers – heightened interest in the way that sport and fashion coalesce. This year, according to Mr Porter buying manager George Archer, “The preppy trend is progressing with a more contemporary approach referring to the 90s with looser fits, pops of colour, statement bags, mixing fabrics, and loafers.”
The Brands Doing It Best
The preppy, laissez-faire approach to menswear of Drake’s has made it one of the most talked about British brands. Working out of Savile Row, it’s authentic, its social media imagery is alluringly grainy, and it recently collaborated with preppy American hero Aaron Levine.
A Brit revitalising the aesthetic is Jonathan Anderson. The son of an old Irish rugby captain, he’s used large block colours, open contrast collars and boxier fits to bring fresh energy to his own JW Anderson rugby shirts. V-neck sweater vests and boat shoes defined his SS24 campaign for Loewe, and 2025 has already brought another of his wearably preppy collaborations with Uniqlo. Wales Bonner is a homegrown talent creating an intoxicating new fusion of Black heritage and British preppiness, while L.E.J London’s unique take revolves around excellent fabrics, innovative styles and goofy imagery.
Crossing the Atlantic, it would be sacrilege not to start with Polo Ralph Lauren. Its iconic madras shirts, khaki bottoms, cable knits, polos and caps remain preppy to the core. More recently, Aimé Leon Dore has had a huge cultural impact, taking the ease, comfort and slight dressiness of key preppy styles, and weaving them into US-centric narratives of streetwear, workwear and even Western style. ALD has shown us all that it’s possible to play with preppy style and look cool, not elitist. New York-based Rowing Blazers leans into the eccentricities of preppy style while, on the West Coast, The Elder Statesman has broadened preppy’s range to embrace vibrant colours, forceful patterns and sensual fabrics.
Around the world, Auralee Tokyo has a refined yet expressive Japanese take on preppiness. Bottega Veneta adds a high fashion edge to it with chunky crewneck knits, leather jackets and, of course, delicious leather bags. The Danes of Les Deux offer a more accessible, contemporary interpretation, while classic French shoemaker Paraboot has become a preppy brand du jour thanks to some choice partnerships with Studio Nicholson and Our Legacy.
The People Doing It Best
Jacob Elordi had a head start by starring in a film positively dripping in nostalgic preppy vibes: Saltburn. The Aussie has since flaunted preppy outfits on chat shows (there was one particular grey fluffy Ami knitted polo) and in a chic Bottega Veneta campaign.
Jason Jules, also known as @GARMSVILLE, not only wrote the book on Black Ivy style. He embodies it through his socials. He also worked with Tyler, The Creator on his collaboration with Louis Vuitton. Tyler’s been a key creative force in blending preppy with other subcultures, using loose skateboarding fits to update preppy’s classic beige trousers.
Finally, that man Aaron Levine, whose groundwork at Abercrombie did so much to revive the preppy aesthetic, continues to move the needle on his own terms. He’s fronted lookbooks for ALD – arguably now the most culturally powerful modern preppy brand – collaborated with Drake’s and, late last year, launched his own label.
5 Tips For Embracing The New Preppy
Step Up Your Shoes
Ditch the gauche trainers and get yourself some loafers (G.H. Bass, Tod’s, COS), derbies (the Paraboot Michael, Dr. Martens, Dunhill) or boat shoes (Timberland, Sebago).
Relax Your Shirts
Embrace new-style loose rugby shirts with contrast collars and minimal block designs – COS has some great ones. Nothing denotes preppy like a lightweight striped shirt, but it doesn’t have to be an oxford – try L.E.J London for more louche cuts. Near Savile Row the other day, we saw someone pop a rugby shirt over a shirt and tie. It worked a treat.
Put Your Tie Back On
You may recently have heard men in bars reporting in hushed tones that ties are back. That’s the preppy effect. Go-ahead characters are styling ties with laid-back looks to create the formal-informal dynamic that preppy thrives in. Head to Moss on the high street or Drake’s for something higher end.
Invest In Knitwear
A choice piece of knitwear can stratify anyone’s look. Put a sleeveless knit over a striped shirt and tie, or keep things minimal and modern with a long-sleeved polo. If in doubt, you can always revert to a chunky crewneck.
Throw On A Blazer
The preppy look is built around separates not suits. Try a dark navy blazer with a beige chino or a tweed one with casual jeans.
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