The age-old allure of preppy style: from Rihanna and Hailey Bieber’s twinning moment, to Saltburn’s Jacob Elordi and Barry Keoghan, and even British royals in The Crown, Ivy League fashion staples endure

Mar 10 , 2024

Who wore it best? Rihanna and Hailey Bieber show preppy style, snapped wearing the same polo shirt two days apart in March 2023. Today, Saltburn’s Jacob Elordi and Barry Keoghan, and the cast of The Crown, are reinforcing the trend. Photo: Bauer-Griffin/GC Images

Born on crusty US campuses in the 1910s, crisp, Wasp-y fashion has been channeled by everyone from 60s counterculture figures Mick Jagger and David Hockney, to Princess Diana and Chloë Sevigny

Rihanna and Bieber famously wore the same rugby shirt 2 days apart, and today Gucci, Louis Vuitton, Loewe, Ralph Lauren, JW Anderson, Marc Jacobs, Ambush, Dries Van Noten and Thom Browne have all jumped on the bandwagon

Amid the slew of so-called fashion aesthetics in recent years, from “dark academia” to “old money”, one constant has held – the practically eternal appeal of preppy style.

What’s more, this elemental way of dressing – of crisp classics and WASP-y traces, of reliable old faithfuls and time for leisure – is a ready foundation for adding your own twist.

Preppy style might have its origins in the early 1910s in Ivy League universities and was particularly popular in the 1950s, but it’s cycled through dozens of iterations. This includes the “Sloane Ranger” style of the 1980s with Princess Diana, the most famous one of them all with her pie crust collars and gingham trousers. Ralph Lauren also reimagined the American dream with the launch of his eponymous brand in this time. Throughout history, and cultures around the world, the facets of preppy style have been twisted and reshaped.

Jacob Elordi and Barry Keoghan in Saltburn

Ralph Lauren and J.Crew (which relaunched in 2023 under new designer Olympia Gayot) have widened the audience for preppiness, while pop culture returns to it time and again, such as late last year with Saltburn, set in Oxford circa 2006, with prime posh boys in popped collar polo fodder.

The most recent season of The Crown, which focused on Prince William’s university days, was also a lesson in posh preppiness. Both are a reminder of how pervasive and recognisable the style is, but also how far it can be stretched. Especially now.

This is evident in the slew of designers who have put their own twist on tropes of preppiness.

This includes Thom Browne’s naughty school boy shorts and Emily Adams Bode Aujla of Bode working the feeling of New England heirlooms into her embroidered and patchwork pieces. Rowing Blazers is a winky nod to leisurely pursuits, and rugby stripes have been spied at the likes of Loewe, Dries Van Noten, S.S. Daley, Ambush and JW Anderson. Meanwhile, there were finely woven polos at Sabato De Sarno’s debut for Gucci and at the most recent Miu Miu show – and Taylor Swift recently wore a polo on a night out in New York. Anyway, don’t we all know that nobody subverts a trope like Miuccia Prada?

As cultural critic Avery Trufelman said in her seven-part deep dive into the history of preppy style on her podcast Articles of Interest, the fascinating thing about such prescribed pieces – from polos to chinos – is that they inspire both creativity and opportunity to experiment. It’s an invitation to rebel.