How To Master The Preppy Trend This Winter
The secret to elevating collegiate classics for 2025? Go against the grain with remixed silhouettes, street-smart accents and playful proportions
There’s a reason preppy dressing has never really gone out of fashion. Blazers, cable knits, penny loafers: those building blocks of the preppy wardrobe are the definition of timeless classics. But how can one reinterpret those pieces in a way that feels fresh, elevated and, dare we say, cool? If the recent runways were anything to go by, the secret lies in playing with contrast and proportion.
At Dries Van Noten, deconstructed sweatshirts were styled with gathered skirts and relaxed pants, while Loewe’s Jonathan Anderson layered V-neck sweater vests over shirts and ties. Elsewhere, Gucci reworked classic polo knits with crystal-embellished collars, and Rabanne styled heritage-tweed blazers with fuzzy checked cardigans and chunky brogues.
Read on for five ways to wear the trend now…
A high-low mix
Tracksuits and tailoring may not seem like the most obvious pairing, but as editors and influencers proved throughout fashion month, they are the perfect match. To nail the ‘chic sportif’ look, balance the sportiness of Sporty & Rich’s ‘Vendome Resort’ sweatpants with a sharp blazer by Brunello Cucinelli – the latter’s nipped-in yet softly structured shape keeps things polished without losing any of the look’s relaxed appeal. Finally, swap your trusty sneakers for a pair of plush red velvet slingbacks by Manolo Blahnik and amp up the cool-girl vibes with a pair of Dior Eyewear’s cat-eye sunglasses.
The wear-anywhere field jacket
Field jackets made a welcome return to the runways last season and have barely been out of the spotlight since. For FW24, brands such as Toteme, Altuzarra and Isabel Marant have put their own spin on the utilitarian staple. Made from hardwearing cotton-canvas, Marant Étoile’s ‘Kimelia’ style comes in a versatile ecru shade and has a contrasting corduroy collar. Slip it on over Staud’s ‘Midnight’ cardigan in Kelly-green and Proenza Schouler’s crepon and stretch-knit maxi skirt, then add a pair of slingbacks by Ferragamo or loafers and ankle socks, for a modern take on the prepster uniform.
Tailoring with sneakers
Exquisitely cut tailoring is a shortcut to instant polish, making it an obvious go-to for both workwear and occasions that require smartening up. But don’t neglect its off-duty appeal – especially those wider, looser cuts that promise round-the-clock comfort and exude effortlessness. An unembellished suit in a goes-with-everything hue is the ultimate investment piece and will transition seamlessly from day to night. For contemporary options, look to Stella McCartney, whose houndstooth wool blazer is cut for an oversized fit with face-framing peak lapels, and looks especially polished styled with the coordinating tapered pants – both are from our NET SUSTAIN edit. From there, it’s all about those thoughtful styling additions that build on a laid-back feel. Dial things down further with a pair of retro New Balance sneakers, and then swap shirting for a slouchy sweater or logo tee.
The preppy polo
The polo shirt is a cornerstone of preppy style, albeit an often-overlooked basic. But as brands such as &Daughter prove, this flexible piece can offer plenty of versatility beyond the soccer pitch. Lean into the collegiate feel by teaming the label’s relaxed ‘Edith’ style with a loafer or ballet flat – Le Monde Béryl’s ‘Luna’ pair is crafted from biscuit suede and exclusive to NET-A-PORTER. Then, try breaking up the pairing with classic denim – Saint Laurent’s jeans have a V-shaped waist and relaxed straight legs. Finish it off with sleek and sculptural hardware and a polished shoulder bag by Savette for a head-to-toe look that goes against the grain.
The sweater vest
No longer the sole preserve of the golfing green or Ivy League alumni, the humble sweater vest comes in an array of colors and shapes this season. Guest In Residence’s version is patterned with traditional Argyle and comes in a relaxed shape. As for styling, smart pairings will help shed any librarian connotations, as will playful layering, so pile on the preppy classics in unconventional proportions. The Row’s cotton-poplin ‘Maigret’ shirt layered underneath a knitted vest reads as slouchy and cool, while Toteme’s wide-leg pants keep things polished. Finally, ground your look with Gianvito Rossi’s glossy ‘Georgie’ loafers.
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