It’s a fitting lede for a sartorial movement with a collegiate provenance, but a new chapter has been written into the annals of the enduring preppy fashion trend. This season, the scholarly archetypes that make up this mode of dressing, from gathered loafers to tailored blazers, are stepping off campus and onto the streets.
The defining summer look is wearing the same silhouette once beguiled by Patrick Bateman-types, just with the psychotic tendencies replaced with an insouciance and fluid ease. Think of it almost like the uniform of someone who graduated from a private university on the Upper East Side, took a gap year in Paris to discover themselves before returning to New York City with the fluid and artistic flair they absorbed whilst living in the French capital’s sixth arrondissement. Enter: The urban preppy fashion era.
Speaking to Brigitte Chartrand, the chief buying and merchandising officer of NET-A-PORTER, she explains this new wave is a “city-forward take on preppy dressing that feels effortless”. “Celine, Prada and Polo Ralph Lauren are the main references for this trend, and they have given preppy a refreshing feel with refined colour palettes, sports jackets and cable knits, and Versace also added touches of pastel to the trend too.”
This is something that Gab Waller, a leading fashion source who has secured nearly-impossible-to-track-down pieces for the likes of Hailey Bieber and Rosie Huntington-Whiteley, has noticed, too. “People are craving clothes that feel timeless and intentional rather than trend-driven,” she explains over email. “The difference is that no one is following the old rules anymore, and that’s what makes it feel fresh. Today, preppy is just as likely to be styled with streetwear, vintage finds, or a touch of grunge as it is with classic tailoring.
What’s clear is that people are losing connection to the scholarly origins of the trend, despite finding the effortlessly elegant staples of preppy fashion aspirational. Speaking on the specific rise of the urban preppy trend, the Australian-born, Los Angeles-based business owner explains that “Preppy style may have originated in Ivy League spheres, but the people wearing it now have little ties to these institutions,” Waller remarks.
“Brands have evolved alongside their customers, who are living in cities, building careers, going out, and constantly on the go. As a result, tailoring has become sharper, fabrics more refined, and the overall aesthetic has matured, transforming preppy from something that resembles a school uniform into a sophisticated wardrobe designed for contemporary adult life.”
As a result, this elevated interpretation has become a way to balance a contemporary, on-the-move lifestyle that comes with living in a major metropolis with the understated sophistication seen in heritage settings like grammar schools, private members' clubs and exclusive colleges. This trend “borrows the polish of traditional preppy but drops the costume-y feel and swaps it for something fresher,” Waller adds. “A silk scarf might be tied around the head instead of the neck, a great blazer could be worn slightly undone, with the sleeves pushed up and no tie, and loafers may be worn with intentionally visible socks that add contrast.”
What you won’t see as part of the urban preppy fashion trend, however, is anything that feels overly fussy, hackneyed or trite. (Chunky boat shoes and garishly striped rugby shirts, here's looking at you.) This trend is all about rendering core wardrobe staples with a fluid and casual sensibility. These are pieces that require very little thought to be pieced together into an ensemble because of how inherently versatile they are.
Relaxed shirting, delicate knitwear and soft jeans will always feel in place amongst one another, but there are several key pieces that encompass the urban preppy trend better than others. After all, this is clothing for the former bookworms who grew up to have careers at Gagosian and exclusively drink pét nat. Bourgeois, albeit bohemian, uncover the key staples of the movement that swiftly swept Manhattan and Paris below.
The 5 Key Staple Pieces of the Urban Preppy Fashion Trend
1. White Derby Shoes
Style Notes: A core fixture in the wardrobes of Fred Astaire and Serge Gainsborough, it’s hard to believe how fast derby-mania has reached a mainstream audience. Of course, to someone who was a high achiever in their class and never wrote outside the margins, the polished appearance and soft shape will certainly earn this shoe trend a gold star.
A hybrid between a delicate ballet flat and a sturdy gentleman’s shoe, pair your derby shoes with V-neck sweaters rendered in vibrant secondary tones and cropped cigarette trousers.
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2. Ludicrosuly Capacious Bags
Style Notes: A crucial part of the urban preppy trend is a focus on “versatile and elevated dressing”, explains Chartrand. These are pieces that can take you from an early morning coffee at Abeulo in Marylebone to an aperitivo hour at The Marlborough without having you feel out of place in either environment. Consequently, you need a practical carry-all to see you through.
The ludicrously capacious bag is synonymous with the urban preppy set, be it The Row’s Margaux or Manu Atelier Le Cambon. Most likely, you’ll find the Fara Homidi Face Compact, a La Bonne Brosse hairbrush and Bottega Veneta fragrance lurking around the bottom. To evoke the essence of Gretchen Wieners, who you know would be swapping her argyle jumpers and nova check minis for a pair of Saint Laurent loafers and Miu Miu polo, that’s why their bags are so big; they’re full of secrets.
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3. Oversized Belt Buckles
Style Notes: For the uninitiated, the urban preppy fashion trend is being spearheaded by Michael Ryder, the newly appointed creative director for Celine. After cutting his teeth at the maison during Phoebe Philo’s tenure at the brand, he’s fused the American sportswear codes he developed during his time as lead designer of Polo Ralph Lauren with the artistically minimal roots of Celine for silhouettes that are quintessentially urban prep.
He’s to blame for the rise in derby shoes, ‘60s-inspired disc sunglasses and prints-maxxing silk scarves (more on that later). However, one of his biggest ‘isms’ has to be the oversized belt buckle. Slightly reminiscent of the logomania days of the 2010s, this trend takes a quieter approach to signalling designer labels, though it still holds a whimsical element, like it’s been pieced together by a teenager collecting trinkets for their charm bracelet. Saccharine and sleek, this style does the heavy lifting for you.
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4. Quarter-Zip Knits
Style Notes: It would be remiss to discuss the rise of the urban preppy fashion trend without mentioning Matthieu Blazy’s momentous Métiers d'art 2026 Collection for Chanel. In his sophomore collection for the brand, he made the quotidian setting of a downtown subway station the most glamorous place in the world with a cast of Manhattanites that represented the entire cross-section of city life. Mobsters! Waspy mothers! Columbia students!
One of the standout pieces was none other than the quarter-zip knit styled by Indian supermodel-on-the-rise Bhavitha Mandava. It’s this idea of rendering a truly mundane essential through the most opulent lens that summarises the essence of the urban preppy trend. Or, as Waller puts it, “details that show an understanding of traditional preppy style while giving it a fresh, more personal interpretation”.
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5. Silk Scarves
Style Notes: If an image of a Dalmatian wrapped up in a triptych of printed silk hasn’t crossed your social media feeds in the days since Celine dropped its “Infinite Possibilities” campaign promoting its new collection of silk twill squares, then there’s still some learning to do about the rise of the urban preppy fashion trend.
A truly underrated accessory, it takes centre place in the wardrobes of the most casually chic dressers amongst us for the way it can instantly add dimension and intrigue to a trusted ensemble. With this, you’ll look like a member of Slim Aarons’s jet set who’s just returned to the city after a summer skipping around the Mediterranean.
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Meet the Experts
Brigitte Chartrand’s early career began in Wholesale at Diesel, before becoming a stylist, model booker and launching her own brand.
In 2005, Brigitte founded REBORN, a Montreal- based boutique that quickly gained international acclaim for introducing directional brands and genderless clothing to the North American market. Amassing a cult-like following, the boutique was amongst the first to successfully expand into global e-commerce in 2007. Nearly a decade later, Brigitte announced the closure of REBORN alongside a new venture.
In 2014, Brigitte joined SSENSE, a leading cultural platform across ecommerce, community and content globally. Her decade-long tenure began as Womenswear Buying Manager, during which she played a transformative role, renowned for launching emerging talents such as Wales Bonner, Marine Serre, Martine Rose, Charlotte Knowles and Willy Chavarria. Brigitte led the luxury division to secure brands including The Row, Alaïa and Miu Miu, and spearheaded the category expansion of Kidswear, Home and Beauty categories, launching the Everything ElseTM division in 2020. Brigitte left in 2025 as Vice President of Womenswear, Kidswear and Everything ElseTM.
Brigitte joined Net-A-Porter as Chief Buying and Merchandising Officer in July 2025, overseeing all categories- Womenswear, Accessories and Home—under the new leadership of CEO Heather Kaminetsky.
Gab Waller is an Australian entrepreneur whose fashion sourcing service has positioned her on speed dial for celebrity clients and fashion fanatics around the world.
On the back of a fulfilled request for a Celine coat for Rosie Huntington-Whiteley that swept Instagram by storm, all eyes were suddenly on Gab as fashion's best-kept secret. Since then, she has been featured in print issues of Vogue Australia, Elle and Harper’s Bazaar, with additional coverage in Forbes, Vanity Fair, Wall Street Journal, The New York Times, WWD and Vogue. In 2023, Gab became a contributor for Vogue America, with a monthly column titled The Hot List: 20 Must-Have Pieces, According to Instagram’s Favourite Fashion Sourcer.
Currently, Gab resides in Los Angeles and services a growing roster of global clients including Rosie Huntington-Whiteley, Hailey Bieber, Lori Harvey, Khloé Kardashian, Sofia Richie Grainge, Sabrina Elba, Hilary Duff and Behati Prinsloo Levine.