8 of Harry Styles' Most Memorable Style Moments

IMAGE KEVIN MAZUR / GETTY IMAGES

If we were to categorize Harry Styles, we probably wouldn't put him among the most elegant men, instead we'd put him among the most stylish. Don't get us wrong, of course, the British singer's looks are memorable, daring, and very trendy; otherwise, we wouldn't be dedicating an entire story to it. But, what sets Styles apart from other celebs is that he's not 'stylish' in the definition of a tuxedo or black suit, but 'stylish' in the terms of today's most acclaimed luxury brands and designers. Styles has spent years starring in Gucci campaigns and his tour wardrobe is often made by the Italian firm. While the artist (sometimes) plays tricks by characterizing himself as a policeman from the '50s (as in the movie My Policeman), Styles has impeccable taste in clothing that is recognizable wherever he goes.

If we could define the style of Harry Styles, it would definitely be eclectic. One day we see him in a patchwork cardigan by JW Anderson (infinitely replicated and turned into an NFT), another day he plays low-key with a mustache and runner pants in Italy, and another day he turns into a literal disco ball to give a concert. Not to mention, his iconic knitted vest with sheep, a tribute to Princess Diana's, or that look that Timothée Chalamet copied from him. It is also important to mention that Gucci has been a large part of the singer's red carpet looks—especially by his friend Alessandro Michele, who has just handed over the creative direction to Sabato de Sarno. What can we say, you know you're doing it right when a Gen Z icon dresses like you. For this reason, and to honor the singer of "As It Was," we have compiled the eight most memorable outfits from the striking and crazy Harry Styles. We may not intend to dress exactly in the singer's baggy pants and retro blazers, but his looks are certainly a feast for the eyes. Here are the best Harry Styles outfits both on stage, on the red carpet, and even on the way to a shoot.

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November 01, 2022

Photo by KEVIN WINTER / GETTY IMAGES.

You don't see the singer dressed in black often, but this version of the British police suit (without the hat) was the most appropriate option for the premiere of his latest film, My Policeman. A ten out of ten for daring to frame the waist.

April 15, 2022

Photo by KEVIN MAZUR / GETTY IMAGES.
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Here's one of the singer's most recent looks that caught our attention. Plus, the whole world. The embodiment of shining brighter than a disco ball.

May 06, 2019

Photo by DIMITRIOS KAMBOURIS / GETTY IMAGES.

The lightness of the sheer fabric. The drama of the oversized lace. All in contrast with all the tattoos. Not to mention, the Cuban heels—a trick that every man should copy for added height.

May 29, 2022

Photo by JOSEPH OKPAKO / GETTY IMAGES.
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The singer has entered an era where he already has a uniform on stage: sequined jumpsuits, feathers, and Gazelle sneakers. Comfort and spectacle above all.

May 11, 2021

Photo by JMENTERNATIONAL / GETTY IMAGES.

From the oversize cut to the '60s print, everything about this two-piece from Gucci transports us to the mid-20th century. A time that Styles dominates perfectly and that he has been able to pair with a trendy hairstyle at the time.

November 12, 2019

Photo by ROBERT KAMAU / GETTY IMAGES.

How can we forget this iconic moment in Harry Styles' repertoire of looks? The artist wore a blue sheep vest very similar to one that Lady Di used to wear in the eighties, with the difference that hers was red and Styles' was blue.

March 02, 2020

Photo by DIA DIPASUPIL / GETTY IMAGES.

Just like we identify the bandana with Axl Rose from Guns n' Roses, the pearl necklace is all you need to dress up as Harry Styles. If you also add the baby neck and the wide pants with darts, you'll nail the whole thing.

March 14, 2021

Photo by CBS PHOTO ARCHIVE / GETTY IMAGES.
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Another moment for the men's style books was when the singer decided to show up at the Grammys wearing a purple feather boa. Was it necessary for your checkered jacket and corduroy pants outfit? Probably not, but long live maximalism.

FromEsquire ES

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Silvia Gómez
Silvia Gómez is a writer and stylist who is an expert in fashion and trends.
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