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.
