Much like his music, Harry Styles’s fashion sense has evolved over the years. He’s gone from reality television boy bander, with the outfits to match, to a fully grown man reveling in Britain’s long legacy of Rock & Roll eccentrics.
Styles’ taste in clothing has matured, too. While he started his fame journey in matching suits with his One Direction bandmates, the singer’s current style is something more personal. Never one to stick to a traditional shirt and pants, Styles has come to be known for his affinity for high-waisted trousers, chunky necklaces, and sparkly boots. And thanks to his close relationship with former Gucci-turned-Valentino designer Alessandro Michele (and his investment in the rising label S.S. Daley), he never has to worry about running out of any designer clothes to wear on the red carpet. Here, take a look back at Harry Style’s fashion evolution from teenage heartthrob to established fashion risk-taker.
2024: Valentino Show
Styles is a good friend of the former Gucci designer Alessandro Michele, so it’s no surprise he showed up to the Italian’s debut runway show for Valentino in this bright orange sweater.
2023: BRIT Awards
The pop star looked like a modern dandy at the 2023 BRIT Awards in a dramatic black suit with. Klaus Nomi-inspired silouhette by Harris Reed for Nina Ricci—topped off with a sizable floral neckpiece, of course.
2023: Grammy Awards
Styles turned heads at the 2023 Grammy Awards, where he took home the prize for Album of the Year, in a crystal mesh EGONLAB x Swarovski jumpsuit.
2023: Grammy Awards
After strutting his stuff on the red carpet, Styles then switched into a disco ball look from Gucci to perform at the 2023 Grammy Awards.
2023: The Late Late Show With James Corden
It’s no secret Styles enjoys his suits—here, he slipped into a mustard yellow Erdem number during an appearance on The Late Late Show with James Corden.
2022: My Policeman Los Angeles Premiere
This suit is (of course) Gucci, but you’d be forgiven if it came from Star Wars’s imperial dressing department. Styles ditched the open collars and exaggerated lapels of his usual suits to channel something a bit more streamlined and buttoned up, but still decidedly eccentric.
2022: Toronto International Film Festival
While the film festival premiere of My Policeman took place in Canada, Styles was channeling something a bit more Irish with this Gucci ensemble’s take on multiple shades of green.
2022: Venice Film Festival Press Call
Before White Lotus’s second season even premiered, Styles was giving a crash course in how a British dandy dresses for a jaunt to Italy during the Venice Film Festival.
2022: Spotify Celebrates Harry Style’s Album Release
For an event celebrating his third studio album, Styles went a bit more casual, wearing jeans and a white tee with a brown duck-covered cardigan from S.S.Daley on top. He finished off the look with his favorite necklace as of late, courtesy of Miami-based jewelry brand éliou.
2022: The Howard Stern Show
While promoting his new album, Harry’s House, on The Howard Stern Show, Styles wore a quirky look comprised of bright green Gucci trousers and a tee by the brand. He then accessorized with another beaded necklace.
2021: BRIT Awards
The musician donned a geometric caramel wide lapel double-breasted Gucci suit from the fall 2021 collection—with a brown handbag to match—to attend the 2021 BRIT Awards at London’s 02 Arena.
2021: Grammy Awards
At the 2021 Grammys, Harry Styles wore not just one but three different feather boa looks—custom Gucci, of course.
2020: Visiting SiruisXM
Styles nabbed a full look from the Gucci fall 2020 show, including a blue sweater and green trousers, to visit SiriusXM Studios in March 2020.
2020: Visiting SiriusXM and Pandora
The singer mixed it up a bit when he wore a look from the Lanvin fall 2020 collection, though he stuck to his usual signature of a quirky sweater and large trousers.
2020: BRIT Awards
Styles wore a brown double-breasted Gucci suit a top a purple marl sweater, all from Gucci fall 2020 collection. The singer then finished off the look with a pair of Mary Janes and a string of pearls.
2019: Met Gala
For his first (and so far only) Met Gala appearance, Styles wore a custom Gucci look made up of ultra-high waisted pants and a sheer ruffled blouse.
2019: Rock & Roll Hall Of Fame Induction Ceremony
The singer stood with inductee Steve Nicks at the 2019 Rock & Roll Hall Of Fame Induction Ceremony in a velvet blue double-breasted Gucci suit with boot cut pants.
2018: Casamigos Halloween Party
Harry Styles dressed like Elton John for the 2018 Casamigos Halloween party, wearing a custom sequined Dodgers uniform just like the Bob Mackie one John wore when playing at Dodgers stadium in 1975.
2017: iHeartRadio Music Festival
Styles wore this red and blue rhombus-patterned Gucci suit from the cruise 2018 show to the iHeartRadio Music Festival in September 2017.
2017: Dunkirk New York Premiere
The singer ditched his usual Gucci for the New York premiere of Dunkirk, instead opting to wear Calvin Klein pre-spring 2018 black wool tuxedo jacket and Raf Simons shirt.
2017: Dunkirk World Premiere
For his first major movie premiere, Styles went a little more low key in a custom wool mohair double-breasted Gucci suit.
2015: BBC Music Awards
For the BBC Music Awards, Styles wore black and white vertical striped pants and a black shirt.
2015: American Music Awards
Not ever afraid to take a risk on the red carpet, Styles wore a floral Gucci suit with wide-legged trousers to the 2015 American Music Awards.
2015: Billboard Music Awards
Styles blended in with his bandmates in a black suit jacket, tight pants, and a black silk shirt.
2014: British Fashion Awards
Taking a major fashion risk on the red carpet, Styles wore a Lanvin striped suit and black boots to the British Fashion Awards in 2014.
2014: American Music Awards
The One Direction boys went all black for the 2014 AMAs, but Styles stood out with his choice of headwear.
2014: BRIT Awards
Once again, Styles’ love for patterns is evident. At the 2014 BRIT Awards a damask shirt added a bit of interest to an otherwise understated look.
2014: Wish I Was Here Premiere
Styles wore a double-breasted wool coat, gray sweater, and brown suede boots to the premiere of Zach Braff’s Wish I Was Here.
2013: The Class of 92 Premiere
It seems gray sweaters and double-breasted wool coats are Styles’ go-tos for premieres.
2013: This Is Us World Premiere
For the World Premiere of One Direction This is Us, Styles wore a heart print Burberry shirt under a black suit.
2013: Teen Choice Awards
Styles stood out from his bandmates by adding a hat to his Teen Choice Awards look, which also featured a lot of chest thanks to his unbuttoned shirt.
2013: British Fashion Awards
For the 2013 British Fashion Awards, the London megastar showed up in a sheer black shirt, blazer, and scarf.
2012: BRIT Awards
Styles matched with the rest of One Direction in gray suits, adding his own touch with a bowtie.
2010: The Chronicles Of Narnia: The Voyage Of The Dawn Treader Premiere
The boys of One Direction looked dapper, matching in suits for the premiere of The Chronicles Of Narnia: The Voyage Of The Dawn Treader in November 2010.