It’s been a decade since Harry Styles, Vogue’s new December cover star, first won over our hearts when he and his fellow One Direction bandmates appeared on The X Factor. From there, the group was catapulted into superstardom, igniting a global hysteria for the young heartthrobs that hadn’t been seen since the days of the Beatles or Backstreet Boys. Post-1D, Styles has since enjoyed a successful solo career, continuing on an already-impressive run that proves he’s here for the long run. His experimental, often ’70s-influenced sense of style has played a key role in developing his distinctive personality as an artist. 10 years in, Styles’s fashion look is now unparalleled, both on the red carpet and on the stage. In honor of his new cover, Vogue is looking back on 10 years of Styles’s best fashion moments, tracing just how high his fashion game has risen. 

At the beginning of his career, Styles’s fashion M.O. was about blending in and looking cohesive with his One Direction bandmates Zayn Malik, Niall Horan, Liam Payne, and Louis Tomlinson. They would hit the red carpet in sleek suits that were similar, but never matchy-matchy. Even then, while the looks were relatively classic, he showed hints of flair, rocking a bowtie or slimmer silhouettes that subtly strayed from the norm. As the band matured, so did their looks; around 2015, Styles began mingling with the high fashion crowd, sitting front row at shows like Burberry with a sharp new English tailoring look to go with it. 

Then, Styles got Gucci-fied. When creative director Alessandro Michele joined the Italian fashion house as creative director in 2015, the designer instantly latched onto Styles as a muse, dressing him in his groovy suits and pussybow blouses that blurred the line between menswear and womenswear. When Styles wore a floral Gucci suit to the American Music Awards complete with a flared pant, the moment went viral for all the right reasons. People weren’t quite ready for it yet, but five years later, the ’70s look is now dominating all the runways. He was way ahead of the curve. 

The star has been working with stylist Harry Lambert for a few years now, and together, they frequently play with fashion—a refreshing approach in a sea of too-safe suits among male stars. This excitement around style is something Styles touched upon in his new Vogue profile, written by Hamish Bowles. “The people that I looked up to in music—Prince and David Bowie and Elvis and Freddie Mercury and Elton John—they’re such showmen,” Styles said. “Now I’ll put on something that feels really flamboyant, and I don’t feel crazy wearing it. I think if you get something that you feel amazing in, it’s like a superhero outfit. Clothes are there to have fun with and experiment with and play with.”

This past year or so, Styles has been proving he’s got a knack for suiting and tailoring in particular; he’s worn sharp, double-breasted styles with a pearl necklace, or flared trousers with heeled boots. He’s rebuked gendered style and worn looks from the womenswear runways, including a zingy yellow Marc Jacobs suit earlier this year. And who could forget his sheep-covered sweater vest last year, too? A Styles look today always ignites conversation around the water cooler (or rather, Twitter), and that’s exactly what good celebrity style should do. He just so happens to be the king of it. 

Below, 10 years of Styles’s fascinating fashion evolution.