How To Master The Preppy Trend This Winter
The secret to elevating collegiate classics for 2025 and beyond? 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-knit sweaters, 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.
Khaite’s creative director Catherine Holstein turned collegiate argyle knits into a cool-girl staple by styling hers with red leather pants and chunky faux-fur coats on the fall/winter ’25 runway. While Bally gave sleek pencil skirts a preppy feel in blanket checks, with neat knits tucked in that had smart shirts peeping out over the collar. When it comes to styling off the catwalks, it’s all about not going too literal. Read on for three ways to wear the trend now…
No longer the sole preserve of the golfing green or Ivy League alumni, argyle patterned knits and sweater vests come in an array of colors and shapes this season. Khaite’s aforementioned iteration comes in a relaxed shape with elbow-grazing sleeves and is a fashion editor favourite this season, while Polo Ralph Lauren’s cable-knit sweater vest arrives in a trending pillar-box red and is perfect for layering over everything from shirts to fine knits. As for styling, smart pairings will help shed any librarian connotations, as will playful layering, so pile on the preppy classics in unconventional proportions. TWP’s wool culottes, for example, will look relaxed yet polished with a pair of Arch4’s cashmere socks and loafers. For something more classic, consider Loulou de Saison’s brown tailored pants with Alaïa’s square-toe leather pumps.
KHAITEAnders argyle cashmere and mohair-blend sweater£1,092.00View Product DetailsSelect a Sizex small - low stocksmall - low stockmedium - low stocklarge - out of stockx large - out of stock
TWPStefens pleated wool culottes£165.00View Product DetailsSelect a Size0 - out of stock2 - out of stock4 - out of stock6 - low stock810 - out of stock12 - out of stock
ARCH4Lucia set of three ribbed cashmere socks
ALAÏA90 leather pumps
The polo shirt is another cornerstone of preppy style, albeit an often-overlooked basic. But as brands such as Róhe prove, this flexible piece can offer plenty of versatility beyond the rugby pitch. Lean into its polished feel by teaming the brand’s relaxed wool and cashmere-blend style with a loafer, such as Gianvito Rossi’s ‘Georgie’ style from our NET SUSTAIN edit. Then, try breaking up the pairing with classic denim – Re/Done’s straight-leg ‘The Thrasher’ jeans have a relaxed fit that stops the look from veering too formal. Finish it off with a sleek and sculptural bag like Jacquemus’ ‘The Turismo’ tote for a head-to-toe look that goes against the grain.
RÓHEWool and cashmere-blend polo sweater£196.00View Product DetailsSelect a Size34 - out of stock36 - out of stock38 - out of stock40 - out of stock42 - out of stock44 - out of stock
FRAMEStriped cotton-poplin shirt£144.00View Product DetailsSelect a Sizex small - out of stocksmall - out of stockmedium - low stocklargex large - low stock
RE/DONEThe Thrasher low-rise straight-leg jeans£143.00View Product DetailsSelect a Size24 - out of stock25 - out of stock26 - out of stock27 - out of stock282930
GIANVITO ROSSIGeorgie patent-leather loafers£845.00View Product DetailsSelect a Size35 - out of stock35.536 - low stock36.53737.538 - out of stock38.5 - out of stock39 - low stock39.5 - low stock4040.54141.5 - out of stock42
Speaking of which, don’t neglect the off-duty appeal of exquisitely cut tailoring, especially those wider, looser fits 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 The Row – its ‘Igor’ pants are tailored from cotton and cashmere-blend gabardine with a pleated wide-leg silhouette for effortless elegance. From there, it’s all about those thoughtful styling additions that build on a laid-back feel. Dial things down with a pair of retro Adidas Originals’ ‘Samba OG’ sneakers and then swap shirting for Wales Bonner’s track jacket.
WALES BONNERMantra knit-trimmed embroidered jersey jacket£238.00View Product DetailsSelect a Sizex small - out of stocksmall - out of stockmediumlarge - out of stockx large - out of stock
SAINT LAURENT EYEWEARJacques D-frame acetate and silver-tone sunglasses
THE ROWIgor cotton and cashmere-blend gabardine wide-leg pants£1,200.00View Product DetailsSelect a Size0 - out of stock2 - low stock46 - out of stock8 - out of stock10 - low stock12 - out of stock
ADIDAS ORIGINALSSamba OG leather and suede sneakers£38.00View Product DetailsSelect a Size3.5 - out of stock4 - out of stock4.5 - out of stock5 - out of stock5.5 - out of stock6 - out of stock6.5 - out of stock7 - out of stock7.5 - out of stock8 - out of stock8.5 - out of stock9 - out of stock
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