Why we’ll always love a Preppy

The term “preppy” derives from a look first formed on the US East Coast’s preparatory schools among the WASP elites, its assortment of blazers, thick jumpers, Oxford shirts and brogues, cords and scarves and immaculately coiffed hair becoming an easy sartorial shorthand. Now, as then, it suggests wealth, pedigree and casual elegance, which is to say it also stinks of privilege. Often the white type. By rights it should have been cancelled long ago. And yet it – like its close cousin, Ivy League – has instead proved ripe grounds for appropriation, as black creatives such as the late Virgil Abloh or Grace Wales Bonner have taken its codes and spread them far further than the bastions for which they were first designed. The WASPs have been swatted away.

The appeal of preppy never really dies, though it has strong and weak phases. Currently, thanks to catwalk appearances on the likes of Louis Vuitton, Fendi and Wales Bonner, and the acclaim for prep-revival brands such as Rowing Blazers or J Crew (now boasting a new energy thanks to Brendon Babenzien), it is everywhere again. We love it because it sums up the ricocheting love affair between Great Britain and the US: those original items, the rugby shirts and the polos and the tweeds, were of course imported directly from Britain. And we love it because preppy, like all the best styles, survives via small reinventions, forever tweaking its formula to please an evolving clientele.

Alex Eagle cashmere cricket jumper, £530

Fendi leather O’Lock loafers, £685, brownsfashion.com

Right: Nanushka terry-cloth Saber polo shirt, £395, brownsfashion.com

Le 17 Septembre cotton corduroy trousers, £170, mrporter.com

Dries Van Noten cotton Jesper polo shirt, £445, brownsfashion.com

Gant x Wrangler wool and leather varsity jacket, £800

It’s strange: when you call someone “a bit preppy”, you’re probably suggesting they’re a bit staid and twee, fundamentally strait-laced. But the fashion itself is a mongrel of colours and textures, allowing for clashing hues, loud herald motifs and interesting socks. This is surely because the basic classicism of the garments – a well-cut blazer, a timeless shirt – plus the heft of their implied history, anchor all kinds of delirious riffs.

Preppy is rarely an entirely safe look. When you think of who might wear it in popular culture – the characters in The Talented Mr Ripley, say, or Donna Tartt’s The Secret History – you perceive extremely neat people caught up in very murky and sordid acts. We love the smartness, but it’s best with a bit of perversion.

This impression of innocence lost has only increased as America has entered the 21st century. Preppy’s early 20th-century charm has gained a certain poignancy; it signifies a hope and freshness about a country that it feels harder than ever to believe in. Consider the journey of the artist now known as Ye, last seen stomping around a dystopian muddy catwalk or tweeting God-knows-what. Once upon a time, he was a budding genius called Kanye West, about to release his first album, The College Dropout. His look was staple prep: hyper-coloured rugby tops, cute jumpers and a truckload of perky ambition. Who doesn’t long for that era now?  

Model, Fausto Sylvester at Established. Casting, Tiago Martins at Ben Grimes. Hair, Hiroki Kojima at Caren using Oribe. Make-up, Dan Delgado using Chanel. Photographer’s assistant, Tom Oritz. Stylist’s assistant, Ady Huq