Harry Styles Red Carpet Looks Have Come A Long Way From His Matching Boy Band Days

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Harry Styles poses for The 2021 GRAMMY Awards
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Alongside his music, Harry’s Styles sense of style has evolved over the years—and seemingly, both just keep getting better. After much anticipation, the singer released first solo album in 2017, featuring his first hit single “Sign of the Times.” The song is a sprawling five minutes and 41 seconds that touches upon musical styles of both Queen and David Bowie —a far cry from his teeny-bopper One Direction days. Then came the Stevie Nicks-approved Fine Line in 2019, which really solidified just how grown up the musician has become. Through it all, Styles’ taste in clothing has matured as well. While he started off his fame journey in matching suits with his One Direction bandmates, the singer’s current style is clearly all his own. Never one to stick to a traditional shirt and pants, Styles has come to be known for his affinity of high waisted trousers, chunky necklaces, and sparkly boots and thanks to his close relationship with Gucci’s Alessandro Michele, he never has to worry about running out of any of those. Here, take a look back at his style evolution from teenage heartthrob to established fashion risk-taker.

2022: Spotify Celebrates Harry Style’s Album Release
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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
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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
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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
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At the 2021 Grammys, Harry Styles wore not just one but three different feather boa looks—custom Gucci, of course.

2020: Visiting SiruisXM
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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
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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
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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
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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
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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
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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
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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
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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
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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
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For the BBC Music Awards, Styles wore black and white vertical striped pants and a black shirt.

2015: American Music Awards
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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
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Styles blended in with his bandmates in a black suit jacket, tight pants, and a black silk shirt.

2014: British Fashion Awards
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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
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The One Direction boys went all black for the 2014 AMAs, but Styles stood out with his choice of headwear.

2014: BRIT Awards
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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
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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
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It seems gray sweaters and double-breasted wool coats are Styles’ go-tos for premieres.

2013: This Is Us World Premiere
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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
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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
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For the 2013 British Fashion Awards, the London megastar showed up in a sheer black shirt, blazer, and scarf.

2012: BRIT Awards
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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
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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.

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