The rules of preppy dressing for grown-ups
The summer holidays are over, and we’re on the cusp of a new season. Suddenly, crumpled linens and flip-flops no longer feel right. September calls for polish, and nothing evokes ‘new term’ dressing like the preppy aesthetic.
It’s a look so timeless that it doesn’t really qualify as a trend. After all, button-down shirts and chinos have never really fallen out of fashion. Diane Keaton’s wardrobe in Annie Hall looks as chic by 2023 standards as it did when the film came out in 1977.
Bio acetate glasses, ￡129, Jimmy Fairly; Merino wool cardigan, ￡220, Sheep Inc.
The lasting appeal comes from the fact that preppy style is inextricably linked to our perceptions of class. It began with the monied British and American university students of the early 1900s, who combined tennis, polo and rugby gear with tweed blazers and knitwear.
Cotton blend shirt, ￡125, Wax London; Cotton and wool trousers, ￡225, Toast; Leather loafers, ￡260, Duke + Dexter
It didn’t gather steam among the wider population until the 1950s, but its influence was cemented in 1965 when Japanese photographer Teruyoshi Hayashida published Take Ivy, a love letter to the preppy look featuring images of male Ivy League students.
‘For many menswear aficionados, Take Ivy is the guide, the bible, for nailing the preppy look,’ says journalist Avery Trufelman, who dedicated a season of her excellent podcast, Articles of Interest, to the ‘Ivy’ aesthetic.
Since then, preppy has been repackaged over and over, in fashion, on screen and in popular culture. Ralph Lauren, Princess Diana, Abercrombie & Fitch and Gossip Girl have all kept the preppy flame alive. In 2023 we owe its popularity to Miu Miu, Emilia Wickstead and Dior men’s. We’ve also seen it on Jennifer Lawrence, Katie Holmes and Ryan Gosling.
The best thing about ‘prep’ is that it doesn’t require a whole new wardrobe. This is more about how to wear the clothes you already have: a shirt, but buttoned to the top or with a knit over the shoulders. A suit, but with a T-shirt underneath. Loafers, but with contrasting socks.
Waistcoats, pleated skirts and polo shirts are staples (the latter named by Ralph Lauren in the 70s – no matter that it was originally designed for tennis by Jean René Lacoste 40 years prior). It shouldn’t look too studied; there needs to be a nonchalance. If it looks a little Carlton from The Fresh Prince of Bel-Air, you’ve gone too far.
The goal is to appear wealthy, sporty and a little bit nerdy. It’s all about class, in every sense of the word.
Shop the looks
Linen skirt, ￡89, Olive; Leather shoes, ￡110, Vagabond
Half zip jumper, ￡32, Marks & Spencer; Mac, ￡125, Kin at John Lewis
Merino wool vest, ￡120, Sheep Inc.; Leather bag, ￡120, & Other Stories
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