Always in style. Harry Styles is the definition of a trendsetter, giving Us all kinds of gender-fluid looks we can obsess over. From his always iconic 2021 Grammy’s outfit that served major Clueless vibes to his Gucci suit from the BRIT’s that Jennifer Aniston rocked months later, the 28-year-old singer has become a fashion icon.
He cemented his status in the style space when he made history as the first-ever solo male to appear on the cover of Vogue — in a dress no less. For the December 2020 cover, the former One Direction alum dazzled in a Gucci ballgown.
In the accompanying article, The Policeman star explained that he sees clothes as a medium to “experiment” with. “What’s really exciting is that all of these lines are just kind of crumbling away,” he said. “When you take away, ‘There’s clothes for men and there’s clothes fro women,’ once you remove any barriers, obviously you open up the arena in which you can play.”
While many applauded the groundbreaking moment, conservative author Candace Owens slammed it on Twitter, writing that the west needs to “bring manly men back.”
Stars such as Jameela Jamil, Olivia Wilde (who is now dating the star!) and Zach Braff took to social media to defend the British pop star. “Harry Styles is plenty manly, because manly is whatever you want it to be, not what some insecure, toxic, woman-hating, homophobic d–heads decided it was hundreds of years ago. He’s 104% perfect,” Jamil wrote. “Also…he looked fit as f–k.”
A few months later, Billy Porter slammed Vogue’s decision to put Styles on the cover in a dress, claiming that he was the wrong person to “represent this new conversation” about gender fluid fashion. The Pose later went on to issue an apology.
The “Watermelon Sugar” singer’s fashion might be making headlines now a days, but his love of fashion seems to have blossomed at a young age. “As a kid I definitely liked fancy dress,” he told Vogue. And his mom Anne Twist takes full responsibility for introducing it to him.
“I think maybe I had something to do with [his style] because I was always a big fan of doing fancy dress with the kids when they were smaller, which Gemma [Styles’ sister] hated but Harry always embraced,” Twist said during a November appearance on the U.K. talk show Lorraine. “Who doesn’t love doing a bit of dress up?”
So from magazine covers to red carpets, keep scrolling to check out Styles’ biggest, best fashion moments of all time. Because from his 2019 Met Gala ensemble to his stellar streetwear, we’re rounding ‘em all up, ahead!