Harry Styles’ Best Fashion Moments – WWD

A look at the singer and actor’s fashion highlights.

9/22/17 3
He is very comfortable playing with retro references. This red and black argyle suit with sharp shoulders and bell-bottoms is a clear example. The pussy bow blouse, another one of his favorite touches, works well and enhances the harlequin twist.

5/6/19 2
This was a bit of a disappointment. When you’re leading the game of breaking boundaries — and the Met theme is camp — you’re expected to deliver. This sheer Edwardian black shirt paired over black slacks falls flat — it’s just boring.

2/18/20 4
White lace gloves, paired with a whole white lace outfit, including the ruffle detail of the sleeves, is giving major Prince flashbacks. No one can pull it off like Prince, but this ensemble, accessorized with matching suspenders, is all in all a cool look and it feels very Harry.

3/14/21 4.5
This was a good take on dorky-chic. The yellow tartan cropped blazer with matching mask, layered over a pink plaid sweater vest gave math teacher vibes, but the purple boa was what stole the show. In general, wearing a boa most of the time is a great idea.

4/15/22 5
A disco-inspired silver sequined jumpsuit with exaggerated cleavage is just the thing for Coachella. But when you add the tattoos and the attitude of Harry Styles, the result gets close to iconic. You should definitely try this at home.

5/19/22 4
In some cases, the concept of runway to reality is difficult to execute, and this striped jumpsuit from JW Anderson seemed to be one of those cases. However, Harry makes this striped Teletubby look work in his favor.

10/30/21 4
You know you’re successful at pushing the boundaries when you’re dressed like a baby Dorothy and it’s not clear if it’s another stage outfit or Halloween. Regardless, he makes it work. The result is fun and carefree.