Singer Harry Styles’ Best Fashion Moments: Photos

He proudly wears sheer tops, flared bell-bottoms, heels and pearl necklaces at concerts and appearances. His gender-fluid affair with fashion has carried over to his real-life relationship with actress Olivia Wilde.

As OK! exclusively reported, the two lovebirds are sharing each other’s clothes. “Harry proudly announced on the cover of Vogue that he enjoys wearing dresses so it shouldn’t come as too much of a surprise that he likes wearing Olivia’s clothes,” a source dished to OK!. “Olivia is cool with Harry’s sense of style and happy to let him borrow whatever he wants from her closet.”

Scroll through to see Harry Styles’ bold take on fashion.  

Even from the beginning, Styles was unafraid to wear accessories. During his X Factor audition he loaded up on bracelets and a long, flowy scarf. 

As a solo artist, he has continued to break the norm. In his music video for “Watermelon Sugar,” he wore bright blouses and over-the-top sunglasses. 

Even during his 1D days, Styles was a trendsetter. He routinely rocked fashionable pieces, such as a sherpa vest while doing a soundcheck in Los Angeles.

Styles has a way of mixing colors together that blends so effortlessly. 

Not a lot of men are brave enough to wear pearls, and yet Styles wore them proudly at the 2020 Brit Awards. 

The singer was sheer perfection at the 2019 Met Gala celebrating Camp as he flaunted his tatted body. 

Styles broke the internet when he defied gender norms on the December 2020 cover of Vogue — where he sported a lace-trimmed dress and Gucci jacket. He also made history as the first solo male to be featured on the fashion magazine cover.