If there’s anyone who knows how to walk the fine line of fashion, it’s Harry Styles.

Through the years, the One Direction alum has served up plenty of memorable looks both on and off the stage. Take the 2021 Grammys, where he walked the red carpet in a yellow plaid blazer—a piece reminiscent of Cher Horowitz’s wardrobe in Clueless—and a purple feather boa. When it was time to perform his smash hit “Watermelon Sugar,” Harry stole the show by swapping his ‘fit and going shirtless underneath a custom Gucci leather suit. 

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“Clothes are there to have fun with and experiment with and play with,” he said of his sartorial approach in a 2020 Vogue cover story, in which he wore a dress in the accompanying photo spread. “When you take away ‘There’s clothes for men and there’s clothes for women,’ once you remove any barriers, obviously you open up the arena in which you can play.”