From X Factor Onesies to the Row, Revisit 33 of Harry Styles’s Best Looks To Date

“Erm,” said Harry Styles when he made his television debut in 2010. “I work in a bakery? And I, like, serve cakes in the shop bit...” Then 16, the erstwhile One Directioner was dressed in a long-line cardigan and a scoop-neck tee with a thin scarf—printed with what looked like ancient hieroglyphs—looped around his neck. There was also a fabric bracelet, a “manacle” as it were, rolled up the length of his forearm. All of that was considered a real expression of someone’s fashion capital in the 2010s, particularly if that person’s Avenue Montaigne was a Topman in Redditch. But less than a decade—and a string of record-breaking world tours, albums, brand launches, high-profile romances, and Beatlemania levels of adulation—later, pop culture would elect Styles as its menswear god. Harry Styles’ best outfits reflect his continued creation evolution.

Much of this was because Styles—in the tradition of a great number of performers before him—wore pearl necklaces and pussy bow blouses and high-waisted trousers and a woefully-underreported saloon dress. Even if the musician’s personal wardrobe rarely went beyond the limits of a cropped tee and jeans, his on-stage persona—masterminded by the stylist Harry Lambert and Gucci’s former creative director Alessandro Michele—was one of flamboyance: taut bod sprinkled with artfully-distanced tattoos but swathed in lime-green feather boas and sequined flares and fuchsia jumpsuits. A swaggering sex symbol rooted not in sleaze but silliness.

Now 31, Styles is a brand founder and an angel investor in the British label SS Daley, sitting front row at the Liverpudlian’s London Fashion Week show in September. And though he seems to be taking a moment of respite from the public eye, his influence can be mapped across 2025’s heartthrobs: among them Timothée Chalamet, Kit Connor, Barry Keoghan and Jacob Elordi, who seem to have built their own image upon Style’s glittering blueprint. See also: the sheer number of heterosexual, civilian men who now feel emboldened to wear pearl necklaces—and the occasional bit of nail polish if they also happen to be amateur poets—on a night out. The only thing that is unforgivable—in my opinion—is the mainstreaming of one (one) dangly earring. It just about worked for a Met Gala themed around the word “camp”…Less so on my friend’s boyfriend who has made the courageous decision to experiment with songwriting.

In a bowling-pin shirt from Miu Miu’s spring 2000 collection, 2026.

Photo: Johnny Dufort

And yet, since stepping back from music after the runaway success of his 22-month Love On Tour in 2023, it has been Styles’s off-duty appearances that have proven most compelling: strolling around New York with Zoë Kravitz in long-sleeved T-shirts, Levi’s and The Row loafers; strolling around Hampstead in Olsen-made French worker jackets, Adidas micro-shorts and slimline Dries Van Noten trainers; strolling around Rome with a bomber jacket slung over his shoulder—and more than a few women wishing they were in its place. If these moments proved anything, it was that Styles might (might) be at his most potent when at his most civilian. It’s an idea echoed on the Johnny Dufort-shot artwork for his fourth album—Kiss All The Time. Disco, Occasionally—where he wears nothing more than a Patrick Carroll t-shirt and jeans from The Vintage Showroom.

Scroll down to see Harry Styles’s best outfits over the years.