Six ways to do preppy style today

Boat shoes, cable-knit sweaters and rugby shirts marked with a tiny mallet-wielding man on a horse: preppy style is going nowhere. Nor has the leisure uniform of the ruling classes lost any of its aspirational gloss. While Ali MacGraw’s working-class music student Jenny meant it as a dig in the 1970 movie Love Story — teasing Harvard rich kid Oliver Barrett IV for being a “preppy” — it soon mellowed into something affectionate. However you feel about woven belts, there’s something inarguably refreshing about a crisp collar and a well-proportioned penny loafer.

There’s something refreshing about a crisp collar and a well-proportioned penny loafer

No wonder fashion houses are doubling down on preppy staples. From Michael Rider’s silk scarves, popped collars and Keds-style deck shoes at his SS26 Celine debut in July to Jonathan Anderson’s rosy pink trousers and striped ties at SS26 Dior menswear, designers are determined to mine the preppy seam that has defined the last few seasons at Miu Miu, Auralee and The Row. Perhaps they were eyeing the figures at Ralph Lauren. In the face of tariff uncertainty and a wider luxury slowdown, the undisputed king of unfettered prep’s full-year sales grew eight per cent in 2025 to $7.1bn. 

Perhaps preppy style’s power lies in its shape-shifting sense of irony. Over the decades it has travelled from East Coast yacht clubs to Ivy League college squares, from Black civil rights marches in Alabama to Harlem jazz clubs, and on to the Ginza district in Tokyo and the catwalks of Paris Fashion Week. In this week’s magazine, it arrives in the Normandy countryside. How to master it today? Read on for HTSI’s tips from the experts on modern preppy style.

1. Channel a laidback mood

“I find it better to not focus on the physical elements but the vibe. What prep meant was: a focus on quality and wearing your clothes. The focus on quality elements means that, no matter how you put things together, it just seems to work. A prep does not ‘save the best’ for an event; they work it into their everyday life. It means that you have confidence that you belong, confidence in being OK to not be the loudest in the room.” Amy Smilovic, founder and creative director of Tibi

2. Finesse the fit

“Creating contrast by playing with proportion can really lift a look that would otherwise be very classic and trad. Fit is really important and can make a super simple piece such as a pair of chinos appear modern just by wearing them high on the waist and showing a fair bit of ankle. Meanwhile, mixing pristine items like a freshly pressed white button-down with something worn in, like a pair of battered jeans and loafers, creates a lovely contrast and is a really nice way of bringing a look to life.” Jason Jules, author of Black Ivy: A Revolt In Style (Reel Art Press)

3. Loosen things up

“Preppy as a style is really a smorgasbord of elements that can be interpreted and adapted to give a contemporary edge. I would highlight in particular the approach to fit, layering and simplicity. The classic preppy fits are never snug or restricting. They always look comfortable and relaxed yet elegant. The preppy style is also very much about layering that creates depths in the looks, and it is an approach that we adapt to our looks at Saman Amel today. Lastly, simplicity is key. You wake up, you put on your clothes, and the clothes should serve you throughout the day.” Dag Granath, co-founder of Swedish tailoring brand Saman Amel

4. Unbutton that neckline

“Being able to open up a neckline is important — not to show cleavage or elongate the neck! — but rather to convey ease and a ‘I threw this on and hardly had time to button myself up’ sort of way.” Amy Smilovic

5. Take notes from Tokyo

“The newest book on my preppy list is by Kay Standard Style. It’s called In Love With Ivy. Kay is based in Tokyo and his book charts both the historical and personal evolution of preppy and Ivy style in Japan. It’s a well-crafted, beautifully detailed book and I cannot recommend it enough. It will also fit perfectly into the pocket of your classic navy blue gold-buttoned single-breasted blazer, which is a nice plus.” Jason Jules

6. Don’t forget the edge

“Preppy style — stripy shirts, cricket jumpers, cashmere crewnecks and tailoring — provides a great basis for a uniform. I do try to add edge or sexiness to it, though, with lace peeking through, or a silk shirt unbuttoned, or leather trousers, or sleek jewellery — so it’s not so on-the-nose.” Alex Eagle, founder of Alex Eagle Studio

Models, Achille Genêt and Aboubakar Konté, both at Success. Keny Salgado at Next. Casting, Piergiorgio Del Moro and Helena Balladino at DM Casting. Hair, William Scott Blair. Make-up, Lauren Bos at Artlist. Photographer’s assistant, Pietro Lazzaris. Stylist’s assistant, Anne Voortmeijer. Production, Alix Murat at KO Collective