If there’s a defining text on the contentious idea of prep – a coastal, status-obsessed, artfully crumpled and irreverent take on dressing and living – then it’s 1980’s The Official Preppy Handbook by Lisa Birnbach, Jonathan Roberts, Carol McD Wallace and Mason Wiley. Somewhere between satire and survival guide, it sold a million copies and detailed, among plenty of other things, the best way to take care of madras, which pets are appropriate for a preppy aspirant (dog) and various lessons in etiquette and bougie taste.

Forty-plus years later, preppy and Ivy style is knottier. You’re now just as likely to see someone like Tyler, the Creator in a colourful rugby shirt and Gucci loafers as you are an old-school New Englander who has strong opinions on Hamptons country clubs and the appropriate level of patina on a waxed jacket.

Today’s trousers are wide and double-pleated, everyone wears white socks, polo shirts, deck shoes, sun-faded shorts and sweatshirts tossed over shoulders. Meanwhile, brands such as Aimé Leon Dore and Drake’s have joined the likes of Polo Ralph Lauren to shape this aesthetic.

In a time where trends are nebulous and difficult to pin down, a modern approach to the preppy look has entered the conversation. Looser, cooler, still unapologetically colourful and, crucially, a bit of fun. And forget the handbook, here’s how to do it right.

Light-wash jeans are as integral to the modern prep look as a tennis membership and the right summer plans. Best paired with a worn-in Oxford shirt, tinted sunglasses, battered penny loafers and a dainty dress watch on the wrist. The perennial wardrobe of the prep set starts from the legs up.

“I think in my early thirties, Ivy offered me a smarter look away from the skate clothes I’d been wearing the decade before,” says the artist Wes Robinson. “In my mind, I wanted to look like I was a grown up. And Ivy was a clean and presentable aesthetic, but still cool and uncommon enough in the UK. It allowed growing up but not necessarily fitting in.”

A contemporary take on preppy dressing wouldn’t be complete without good tailoring. These suits are often unstructured with a lighter, looser silhouette than your traditional Savile Row getup, paired with an Oxford or poplin shirt with a silk tie (repp stripe or something with a wild pattern). Or, in the summer months, even a polo or rugby shirt. You’ll get extra points for incorporating a niche baseball cap – something from an obscure tennis tournament or Cayman Islands resort, in a washed-out Nantucket red – into the finishing touches. A true preppy outfit features a mixture of new, high-end and something that’s been inherited or picked up for a song in a dusty vintage shop.

The polo shirt might be an evergreen preppy essential, but the cricket jumper is also back in play. Try a luxury interpretation by the likes of CELINE, worn over a clean, simple T-shirt, such as that by the ascendant A.PRESSE. Founded in 2021 by designer Kazuma Shigematsu, this Japanese brand has turned block-colour sweatshirts, T-shirts and dress shirts into a fine art.

“I don’t necessarily think there has been a ‘resurgence’ of prep or Ivy dressing, so much as every generation discovers Ivy on its own and inevitably filters it through their own lens,” says the menswear writer Eric Twardzik. “As a millennial, I came up with late-2000s’ ‘neo-prep’. Rugby Ralph Lauren, Michael Bastian at Gant, Vampire Weekend, etc. It was, in retrospect, a bit twee and certainly far too tight. I’ve enjoyed Gen Z finding Ivy on their own through a different aesthetic, which feels very informed by 1990s Polo and J.Crew – oversized fits and pleats. Bring it on.”