Harry Styles Turns 27: How His Style Evolved Over the Years

On Monday, February 1, Harry Styles turns 27 years old. He started out as a boy with a dream on Britain’s The X Factor back in 2010. Since then, he has dazzled the world as part of One Direction before emerging as a bold and innovative fashion icon.

Obviously, a major part of innovation is change. And we’re going to take a closer look at the way Harry Styles’ fashion has evolved over the years.

Starting simple

Put simply, Styles was not always a fashion icon. Outside of some fun flair (such as the stylish and skinny scarf he wore to his X Factor audition), he mostly rocked the traditional outfits of a young man. This varied from simple plaid shirts to comfortable tracksuits. Still, the hints were there from the beginning at the direction his style would take.

First off, he clearly loved designer clothing. His looks were tailored, and he’d rock outfits from clothing brands such as Jack Wills. Over time, though, he’d stand out from his friends and bandmates through little touches like bowties and blazers that added up to a big impression.

Simple meets stylish

Styles wasn’t afraid to dress for comfort, though. Although many people noted that he still made comfortable look sexy, including a certain famous female singer!

Harry Styles and Taylor Swift briefly dated during 2012. He dressed pretty down-to-earth around her, but she liked it. In fact, many Swift fans think the song “Style” is about Styles. And it includes lyrics such as “You got that James Dean daydream look in your eye… You got that long hair, slicked back, white T-shirt.”

It’s possible Swift had an influence on Styles’ fashion. After they broke up, Styles started developing signature looks involving tight, fitted jeans, designer hoodies, and leather ankle boots. By the end of 2013 and beyond, Styles was also letting his long hair and scarves fly even as he got multiple tattoos.

Styles meets Gucci

It may have taken Harry Styles a few years to evolve his fashion. But he clearly has good taste because he eventually embraced Gucci clothing as an extension of his brand.

With the help of his stylist Harry Lambert, Styles began rocking Gucci clothing almost everywhere he went. But he added an unexpected twist by wearing clothing that blended masculine and feminine qualities.

For example, he attended the American Music Awards in November 2015 in a floral two-piece. And in the next two years, Styles would lean into the aesthetic by blending blouses, pink suits, killer heels, and stunning jewelry into a look that is entirely his own.

Eventually, the Gucci love paid off when Styles was chosen as the famous face of Gucci’s tailoring campaign in June 2018.

Styles goes Vogue

If you weren’t already aware of Harry Styles’ evolving looks, he made a major splash in November 2020. That was when he appeared on the cover of Vogue and blew everyone’s minds!

Styles made history here by being the first man to make a solo appearance on the cover. And on that cover, he wore both a Gucci jacket and dress, perfectly blending the masculine and feminine. Inside the magazine, he pulled off a  full-length gown and tuxedo-like skirt along with many other unexpected looks.

Today, Harry Styles turns 27. And we have to wonder what new challenges lay ahead for this famous singer and cultural icon. Because when it comes to fashion, Harry Styles is a bit like Alexander the Great: there are simply no new worlds left to conquer!