Beyond being one of the best pop stars we've got (anyone else playing "Daylight" on repeat?), Harry Styles is a fashion god for the ages.
From the super-skinny jeans, Chelsea boots and floppy hair of the One Direction era to the wide-legged jeans, chunky necklaces and retro tees he's been sporting during the promo tour for his third album, Harry's House (out Friday, May 20), the "As It Was" crooner and Don't Worry Darling actor has never shied away from changing up his sartorial game, dipping into the fab flamboyance of '70s rockers Freddie Mercury and David Bowie for the stage and regularly skewing gender normativity with his androgynous choices.
To get you prepped for a brand-new era of Harry (we're all streaming Harry Styles’ "One Night Only in New York" special tonight, right?), in no particular order, we're taking a look back at our favorite fashion moments from the bold Brit. (And, yes, there's a lot of Gucci.)
Harry Styles iconic outfits: our 10 favorite looks
1. Harry Styles Coachella 2022
Okay, this one's kind of a cheat because every single item that Styles wore throughout his two-weekend headlining gig at Coachella this April (all custom Gucci, naturally) was iconic. The pink feathered coat he boogied in with Lizzo to Gloria Gaynor's "I Will Survive." The rainbow-sequined jumpsuit he sported while singing "Man! I Feel Like a Woman!" with Shania Twain. The metallic leather cowboy get-up that revealed his initials embroidered on each butt cheek every time he turned around. 'Chella Harry was a dream, y'all.
2. Harry Styles Met Gala 2019
Harry's status as a fashion power player was cemented when he was invited to co-chair the 2019 Met Gala alongside Lady Gaga and Serena Williams. Arriving with Gucci maestro Alessandro Michele in tow, Styles stunned in a romantically ruffled sheer black blouse, tailored trousers and heeled boots from the fashion house. A single pearl earring capped off the look à la a Vermeer painting, and most memorable Met Gala fashion moments was born.
3. Harry Styles Grammys 2021
Again, technically a cheat and we don't care. Because both feather-boa moments from the 2021 Grammy Awards deserve a place on our list: the black leather suit—worn with no shirt underneath because, hello, this is Harry Styles—green feather boat and heeled boots he performed "Watermelon Sugar" in (another custom Gucci creation, you'll see a pattern here) and the yellow houndstooth blazer, brown velvet pants and purple boa he wore while picking up his Grammy for Best Pop Solo Performance.
4. Harry Styles Brit Awards 2021
Harry already looked like a winner when he arrived to the 2021 Brit Awards in this groovy Gucci number, complete with '70s-tastic flared pants, a large-lapeled blazer and all-over psychedelic print. (Fittingly, he went on to win his first solo Brit Award that night, in the "Best British Single" category for “Watermelon Sugar.”) The only better accessory than his low-top sneakers or bamboo-handled leather bag? A face mask. We love a responsible king!
5. Harry Styles London Fashion Week 2013
An oldie but a goodie: this throwback outfit is classic O.G. Harry. Sky-high hair? Check. Skin-tight denim? Check. A perfectly-pointed leather boot? Check. Attending the Burberry Prorsum show during London Fashion Week SS14, the One Direction boy-bander added just enough style interest with an animal-printed Burberry tee, chicly capped with a tailored coat from the brand, giving fashion fans a peek at the style evolution to come.
6. Harry Styles Love on Tour 2021
Styles' Love on Tour arena tour, supporting his second album Fine Line, was positively packed with memorable fashions, with custom Gucci pieces created by Alessandro Michele and styled by Harry Lambert for every single concert. It was a parade of high-waisted trousers, cheeky suspenders and form-fitting vests, but we're partial to the sequined fringe vests he wore to open and close the tour, the sparkly strips dramatically flying around as he—and we—rocked out to "Kiwi" one last time.
7. Harry Styles Rock & Roll Hall of Fame 2019
If you're going to share a stage with one of rock and roll's most famous and formidable fashion queens, you better bring it. Harry did just that when he honored and performed alongside Stevie Nicks at the 2019 Rock & Roll Hall of Fame Induction Ceremony.
Where our "magical gypsy godmother" (as Styles so fittingly called her) was outfitted in her signature black, the "Sign of the Times" singer opted for a custom, cobalt-blue Gucci with double-breasted blazer and flared trousers. The ensemble was such a hit that the Rock & Roll Hall of Fame added it to the music museum's "Right Here, Right Now" exhibit.
8. Harry Styles Elton costume 2018
Harry has been seen in some memorable costumes throughout the years, from the Little Mermaid look he donned for his 2019 Saturday Night Live appearance to the Gucci Dorothy costume (red slippers included!) he performed in for 2021's "Harryween" in New York City. But our favorite of the bunch is this spot-on homage to his spiritual glam-rock godfather, Elton John, and the crystal-covered Dodger uniform that the "Crocodile Rock" performer famously wore while playing Los Angeles' Dodger Stadium back in 1975.
9. Harry Styles iHeartRadio Music Festival 2017
We'll say what you're all thinking: on anyone else, this would look downright insane. But such is the power of Styles', well, style: his sheer confidence and fashion savviness means that he can pull off a red-and-black harlequin-printed suit, rose-patterned sheer blouse and a white pussy bow all at the same time without looking like Austin Powers or a court jester. On the Englishman, it doesn't look wrong—it just looks like rock and roll.
10. Harry Styles 'TODAY' show 2022
The latest in the ever-growing catalogue of Harry Styles' epic fashion moments is the performer's recent appearance on TODAY's Citi Summer Concert Series on Thursday, May 19, ahead of the release of Harry's House.
Styles wore a candy-striped neon onesie to perform songs off the new record for fans during the televised show, but it's actually the outfit that he wore during soundcheck that caught our attention. Equal parts Penny Lane and Canadian tuxedo, the doubled-down denim look from AMI saw the singer gamely play with proportion, with a cropped jacket and low-rise jeans allowing his many tattoos to peek out. A new era of Styles' style has arrived!
Christina Izzo is the Deputy Editor of My Imperfect Life.
More generally, she is a writer-editor covering food and drink, travel, lifestyle and culture in New York City. She was previously the Features Editor at Rachael Ray In Season and Reveal, as well as the Food & Drink Editor and chief restaurant critic at Time Out New York.
When she’s not doing all that, she can probably be found eating cheese somewhere.
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