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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

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

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.

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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.

Thom Browne cardigan
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.

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“American fashion is bringing itself back, and we want to feel like we can play around in the canon a little more. That’s why you can have Bode pants with writing all over them. We’re getting back to that advanced level of self-styling. We want it to be a little toyed with,” she said in a recent interview on the allure of preppiness and what we want from it.

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The rugby stripe is perhaps the prime example of preppy and its perversions right now. A little muddier and sturdier, thanks to its hurly-burly sporting origins, the rugby stripe is prime for toying with.

Mick Jagger from The Rolling Stones posed wearing a rugby jersey backstage on tour in Scotland in early 1964. Photo: Redferns

Indeed it’s long been worn by true arbiters of style like Chloë Sevigny, Mick Jagger and even artist David Hockney – and more recently Rihanna, and model and beauty entrepreneur Hailey Bieber. The styling of rugby shirts now is what makes them less “freshers on the walk home from a bleary night at the pub” and more, well, cool. At Dries Van Noten, they’re worn with sheer skirts and tailored coats. Bieber wears hers under an oversized blazer. Rihanna wore hers cropped to show her pregnant belly, because of course she did. It’s also not the first time rugby stripes have infiltrated luxury fashion. Marc Jacobs did them for spring 2017, and for the Louis Vuitton autumn/winter 2022 collection, they were paired with sheer frilled floral floor-length gowns. Oh, and Rihanna wore the Jacobs one in 2017 too.

Liane Wiggins, head of womenswear at Matches, agrees that a huge appeal of the new preppiness is that it can be adapted for almost any occasion and sense of style.

Dries Van Noten spring/summer 2024

“Spring/summer 2024 has a preppy new mood as designers reimagine the classic polo and rugby shirts. We have grown our edit for the season by 48 per cent versus last year with options to suit any style – from Sacai’s pleated polo dress to Raey’s black and white cashmere jumper and Dries Van Noten’s colourful oversized rugby shirt,” she says.

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“Whether styling with wide leg denim for the day or dressing up with sequins as seen at 16Arlington, polos and rugby shirts are super versatile. For a more classic take on the trend, look to Ralph Lauren who has always offered great polo and rugby style,” Wiggins advises.

Gucci spring/summer 2024

Libby Page, market director at Net-a-Porter, agrees. She says a “chic sportif” mood is infiltrating customers’ wardrobes right now.

That said, Page is also a fan of Dries Van Noten’s spin on rugby stripes – and says the Belgian brand, which has always moved to the beat of its own drum, is truly resonating for the luxury retailer.

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“Dries Van Noten showed us a masterclass in high-low dressing with rugby-striped pants paired with couture-like coats. This brand has quietly soared for us, and we’ve grown our buy across all categories. We’ll be stocking the sneaker shown on the runway in all four colourways,” she says.

Meg Bellamy and Ed McVey in season 6 of The Crown

Other brands to look for, says Page, include Loewe for its polo-top dresses and fisherman sandals, and JW Anderson.

Accessories such as oversized totes, like Bottega Veneta’s luxurious basket bag and Balenciaga’s charm-adorned top-handle bag, complete the look.

Fashion
  • 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