Over the 20 years since her untimely death, Princess Diana has remained a fashion icon. But the hundreds of thousands of pictures people have been sharing on Instagram lately haven’t all been of her in the elegant skirt-suits and perfectly formal ’80s and ’90s silhouettes we usually associate with the beloved royal. The shots that have been making the rounds lately showcase Diana’s less obviously fashionable, more down-to-earth looks. Think of the Clinton presidency-era sportswear that has made a recent comeback, from the Champion, Fila and Tommy Hilfiger apparel now readily available at Urban Outfitters to streetwear-influenced brands like Noah and Saturdays.
And if you wagered a guess on who some of the biggest contemporary fans of Diana’s style are, you’d probably be wrong. Popular menswear brands like the Rowing Blazers Moodboard and designer F. E. Castleberry have recently shared images of Diana wearing everything from college sweatshirts to Chelsea boots and a Barbour jacket.
Princess Di, it would seem, is a serious men’s style icon.
Diana may have had plenty of ultra-feminine, pastel ensembles, but the casual looks feel most relevant right now, and she was wearing them before “athleisure” became a fashion-world buzzword. Calum Marsh, arts reporter for the National Post, points out that “the combination of laidback street wear, breezy athleisure, and cozy Dunkirk-ish Brit knits is eerily on trend for menswear in 2019, so it’s not surprising that men are using some of her better looks as inspiration.”
While Charles has always looked good in his suits from Saville Row stalwarts like Anderson & Sheppard, the fact is that royalty is antiquated, and it’s way more fun for the rest of us to covet an effortlessly worn sweatshirt than the elitist vestiture of the monarchy. That’s why the low-key looks of Di and Charles are more popular than ever.
“If you really think about it, Princess Diana is the only royal we’ve ever seen wearing sneakers and bike shorts. Even the more ‘modern’ Royals like Kate Middleton are never seen wearing anything even remotely approaching athleisure,” says fashion journalist Isabel Slone.
Diana’s casual style has come under new scrutiny in the age of the influencer. Earlier this year, GQ style writer Rachel Tashjian (who posts a truly inspired selection of Diana images on Instagram) penned a piece proclaiming her “the real king of street style.” Part of the fandom around her casual looks, of course, comes from the classic tension of a high-low mix — one that plays into the American fascination with monarchy with an added 21st-century wink.
Slone acknowledges that Diana’s off-duty outfits weren’t always looked at as her most fashionable. But in the here and now, it seems like pretty much everything from the ’90s has come back in some from or other. As Slone sees it, “Outfits that passed for ‘somewhat frumpy mom in the ’90s’ are now being reinterpreted as the very height of fashion.” A ’90s mom vibe might not sound right for menswear, but Sloane points out that “It’s not hard to imagine Chance the Rapper wearing an oversized Harvard sweater like Di, or some other menswear influencer donning her ‘Fly Atlantic’ Virgin airlines sweatshirt.” Marsh agrees: “A lot of the stuff she wore at the time was deliberately unfashionable, but it’s come around in such a way that now it looks prescient.” That ultra-valuable Virgin airlines sweatshirt “looks like straight-up current-season Gucci.”
You don’t have to be a royal to make a purposefully un-hip sweatshirt look stylish (though it might help). The most important thing is a sense of swagger and a dash of humor. When it comes to Diana’s former husband, Prince Charles, a sense of humor is key in channeling the looks of this more obvious menswear inspiration. Vintage dealer Sean Crowley sees Charles’s more playful ’70s pieces like cabana suits and safari jackets as “fun looks that feel on-trend and relevant.” Marsh, who calls Prince Charles an “absolute style god,” says his casualwear has “started to crop up a lot in influencer circles,” citing a replica of a T-shirt style worn by Charles from trendy New York-based menswear line Rowing Blazers as evidence.
Crowley shares an anecdote indicative of Charles’s approach to style: the Prince once bought a beat-up old pair of boots to a bespoke shoemaker, only to then be frustrated when the shoemaker polished away the dingy markings he cherished. Crowley also sees Charles’s insistence on wearing clothes for years, combined with his environmentalism, as an appealing counterpoint to the fast-fashion epidemic. When it comes to style, Charles is someone who’s “stayed the course,” says Crowley — something that Diana tragically had no chance to do. Part of the mystique of the casualwear photography genre comes from the fact that she was gone too soon. While thousands of stylish pictures of her exist, they are finite, and retain the glow of a pre-social media age.
It may seem counterintuitive to claim Diana as a menswear icon — after all, what’s more stereotypically feminine than a princess? But her playfulness and subversion of norms is a big part of what made her so adored. Years after she first wore them, her sweatshirts and sneakers feel fresh. Such comfy nonchalance can be a source of style inspiration, no matter your gender. With the right attitude, even fleece and cotton can feel regal.
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