Harry Styles is often hailed as one of the most fashionable men on the planet – and for good reason.
Fabulously flamboyant and not afraid to play by his own rules, Styles has become a trailblazer since his solo career took off.
Styles is Gucci’s darling, has hosted the Met Gala, and was the first man to appear solo on the cover of American Vogue.
As the singer gears up to release his highly anticipated fourth album Kiss All The Time, Disco Occasionally , Square Mile looks back on his best outfits over the years.
The early promise
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From June 2012. This one goes out to the OG Harry stans. Not as experimental as his later outfits, but this casual graphic tee and jeans look, served with a dash of irony, shows that Styles has always kept it cool when it comes to fashion.
Purple prince
ARIA Awards – November 2017
The suit to end all suits. This purple paisley ensemble, worn with iridescent gold shoes, was sure to stop traffic. Stepping away from the Gucci for a night, this one is by Alexander McQueen.
Scott Barbour / Stringer
Boy with a pearl earring
Met Gala, May 2019
Hosting the Met Gala, Styles took dandyism to a new level with this Gucci ensemble. The sheer shirt, which revealed his many tattoos, in combination with uber-high waisted trousers and heels was perfection. And don’t miss the single pearl earring *chef’s kiss*.
(Photo by Dimitrios Kambouris/Getty Images for The Met Museum/Vogue)
California Dreamin'
Styles didn’t get much cooler than when he chatted to Zane Lowe from California wearing this Bode calorie print shirt. Paired with a vest – his swallow tattoos just peeping out – and linen slacks, this laidback look took resort wear to a whole new level.
Babar brilliance
Spotify Session – December 2019
Styles wore a graphic Lanvin cardigan (is that Babar the elephant we see there?), classic slacks and Vans when performing a private listening session for fans to launch the Fine Line album.
(Photo by Rich Fury/Getty Images for Spotify)
Gorgeous in Gucci
Sirius XM – March 2020
Did somebody say grandma chic? A classic Styles look here. He wears clashing colours with a blue jumper and green slacks, with a scalloped collar and a string of pearls. All Gucci, of course. We’re starting to wonder whether the singer wears any other designers.
(Photo by Dia Dipasupil/Getty Images)
Dress to impress
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Styles broke the internet with this historic cover shoot, as the first man to appear solo on the front of American Vogue. Styles strikes the perfect balance between playful and regal in this floor-length gown. And you’ve guessed it, it’s Gucci.
Golden Delight
Looking tanned as hell with a striped shirt, aquamarine blazer and patterned flares, Styles wore Gucci Resort while running around Italy filming the Golden music video. In true Styles fashion, he’s also sporting an adorable beaded necklace by Eliou.
Hip to wear squares
The BRITs – May 2021
Picking up his BRIT for Best British Single, Styles looked suave in this 70s-style geometric Gucci suit. Paired with trainers and a handbag no less, making the perfect accessories to go with his new award.
(JMEnternational/JMEnternational for BRIT Awards/Getty Images)
On your bike
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November 2021. Nonchalantly perched on a motorcycle, dressed head-to-toe in custom Gucci, this is Styles at his finest. Not many would think to pair a nipple-highlighting cut out vest with lilac flares, but it’s working for us.
Damn fine dungarees
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We could pick any number of outfits from the iconic Love on Tour, um, tour – Styles rocked up and rocked out with a phenomenal look every night. The heart-shaped dungarees are particularly fine, however, and one of the easier looks to create at home.
It was all yellow
KISS ALL THE TIME. DISCO, OCCASIONALLY.
Very few people in the world can pull off a yellow sweater, maroon tie and oversized sunglasses – let alone make such a combination look cool. Thus the power of Harry Styles, who sports the combination in the publicity photo for his upcoming fourth album. Bonus points for the tea towel – who doesn't love a man willing to muck in with the washing up?
Johnny Dufort
