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Harry Styles’ Style: A Fashion Tour Through His Singles

Harry Styles reinvents his look with each song release—mixing glam, vintage, and bold choices that keep fans guessing and inspired.

Harry Styles wearing a shiny red jacket while performing on stage during the BRIT Awards
Photo by Gareth Cattermole/Getty Images

Harry Styles doesn’t just drop music—he drops looks. Since going solo, the former One Direction star has used each single as a runway moment. Whether he's channeling 1970s glam or rocking pearls with a suit, Styles has become a fashion risk-taker, making every new track feel like a full-on fashion event.

Let’s walk through some of his most iconic single releases and the unforgettable outfits that came with them.

“Sign of the Times” (2017): Moody, Majestic, and Gucci

Harry’s debut solo single, “Sign of the Times,” came with a dramatic video that showed him literally flying through the sky. But just as attention-grabbing was his fashion: long coats, trousers, and rich textures. Around this time, he began a close partnership with Gucci, stepping into his vintage-meets-rock-star era.

His clothes gave fans a peek into the more serious, artistic direction he was heading toward. As GQ noted, “He became a walking mood board of gender-fluid fashion.”

“Watermelon Sugar” (2019): Summer of Retro Love

Cue the color explosion. For the “Watermelon Sugar” video, Styles wore bright colors, funky prints, and pastel nail polish—all beachy, playful, and slightly psychedelic. Think: your coolest uncle from the '70s meets a Vogue cover shoot.

“Golden” (2020): Road-Trip Core with a Twist

In Golden,” Styles runs through the Amalfi Coast wearing open shirts, high-waisted trousers, and even a pair of yellow driving gloves. The whole vibe? Effortlessly free-spirited.

This look screamed “European vacation,” and fashion insiders loved it. “He’s redefining masculinity in fashion,” wrote Vogue in his now-famous December 2020 cover story, where he also wore a dress.

“As It Was” (2022): Red Jumpsuits and Emotional Dance Moves

Styles kept fans surprised with the “As It Was” video, dancing through museums in a sparkly red jumpsuit. He embraced bold silhouettes and performance-focused design—less about looking pretty and more about feeling the song.

“Fashion is something that’s fun,” Styles told Dazed in a 2021 interview. “It’s not about how other people see it, it’s how it makes you feel.”

“Daylight” (2023): Whimsy Meets Theater Kid

Though the Daylight video gave circus vibes, Harry’s fashion gave whimsy—with heart-shaped sunglasses, sparkly suspenders, and playful colors. He seemed to be saying: that fashion should be fun, not fussy.

According to Harper’s Bazaar, his style in this era leaned “more clowncore than couture,” but still felt perfectly Harry.

The Bigger Picture: More Than Just Clothes

Harry Styles’ fashion isn’t just a backdrop to his music—it’s part of the storytelling. Whether he's wearing pearls with no shirt or a giant feather boa at the Grammys, he challenges traditional fashion rules and encourages fans to express themselves however they want.

And just like his music, his fashion keeps evolving—one fabulous single at a time.

Kayla is the midday host on Detroit’s 105.1 The Bounce. She started her career in radio back in 2016 as an intern at another Detroit station and worked her way here. She's made stops in Knoxville, TN, Omaha, Ne and other places before returning to Detroit. She’s done almost everything in radio from promotions to web, creating content on social media, you name it. She’s a true Michigander, born and raised. So, you can catch her camping or vacationing up north to exploring the downtown Detroit or maybe even catching a sports game. During her free time, Kayla enjoys watching movies, roller-skating, crafting, and music festivals. She and her husband together dip into many of the great things Michigan has to offer. Together they also like to travel. A few hobbies of hers include wine and beer tastings, crafting, hiking, roller skating, movies, home improvement projects, gardening, and festivals. She’s always looking to take on more local events happening in the community. She loves connecting with the community. When writing, Kayla covers topics including lifestyle, pop culture, trending stories, hacks, and urban culture.