Celeb Style
Harry Styles Style Evolution

Harry Styles’ Style Evolution Only Goes In One (High Fashion) Direction

I’d give anything to raid the closet in Harry’s House.

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Harry Styles’ final Love on Tour show is on Wednesday, Sept. 21, but I’m not ready to let go of seeing pics of him on stage in sequined jumpsuits. It’s not just because I love a celebrity style evolution. Sure, I’ve been known to wax poetic about a celeb embracing their identity through fashion and beauty, but there’s only one star whose style journey I’ve been with since Day One. From his frat boy fashion days to his reign as the Gucci king he’s become, Harry Styles’ style evolution is one of the most iconic ever.

Ever since Harry Styles first stepped onto the X-Factor stage and sang “Isn’t She Lovely,” I knew my life would never be the same. Now he’s a Grammy-winning artist starring in the year’s most buzzed-about film and I can’t handle how fast he’s grown up. As a long-time Styles fan, I feel like I’ve been there for every change in his aesthetic, and, let me tell you, there have there been quite a few. At this point, I’m practically a seasoned archivist of the former One Direction member’s fashion choices.

I remember spending over an hour attempting to capture the perfect screenshots of Styles from the “One Thing” music video and you don’t have to do much digging to find the Tumblr I may or may not have created to pay tribute to the “Sunflower” singer. (It’s *technically* defunct, but I will still claim the associated street cred.) All this is to say that I’ve spent the past dozen years preparing to catalog and critique each and every step in Style’s fashion evolution. In the famous words of his famous ex, Taylor Swift, he never goes out of style. How could he with all this evolving?

December 2010: Harry Styles’ Prep School Phase

Harry Styles Style Evolution: Harry's preppy fashion for an X Factor secret gig in 2010.

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When One Direction was first formed in July 2010, it was clear the band’s stylists struggled to flesh out each member’s identity. In their defense, the teenage boy aesthetic of the time period was basically gym shorts so there wasn’t much to work with. It appears Styles was assigned a British prep school student fashion persona. At a secret, X-Factor event in December 2010, Styles wore a gray blazer, striped t-shirt, and chinos, which, alongside pea coats and cardigans, would become staples in his first signature look.

November 2011: Harry Styles’ Blazer Era

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After 1D’s first album dropped in 2011, Styles’ fashion got a slight upgrade and the aggressively preppy style he started out with calmed down by November 2011. While he’s still rocking a blazer at a One Direction performance during the BCC’s Children In Need Appeal, the velvet fabric and white T-shirt suggest a move to something less expected and more trendy. It’s not a wildly out-of-the-box look, but it is a step toward what his fashion will become.

July 2012: Harry Styles’ Frat Boy Era

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2012 only means one thing to Styles fans: the start of his Frat Boy Era featuring a rotation of skinny jeans, beanies, and T-shirts. This aesthetic — laidback, casual, and effortless — also marks when Styles started getting tattoos. It’s the era during which, at least off-stage, Styles was calling the shots and the star said goodbye to blazers and bowties.

August 2013: Harry Styles Dips Into Prints

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2013 saw Styles’ get slightly funkier with his fashion as he started getting into the patterns and prints he loves so much these days. At the world premiere of One Direction: This Is Us on August 20, 2013, Styles wore a button-down from Burberry decorated with hearts. While this print has nothing on the styles he’ll wear in 2022, it was 100% the start of something new for him.

December 2013: Harry Styles In Skinny Scarves

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In 2013, Styles also took the time to do one of the most crucial things any fashion icon could do that year. He started rocking scarves. The skinny scarf, one of the fashion’s weirdest trends, became a style-must-have in the mid-2010s, so you know that this 1/5 of One Direction was all over it. He wore a skinny AF scarf to the 2013 British Fashion Awards. That’s icon behavior, have no doubt.

December 2014: Harry Styles’ Double-Breasted Suit Phase

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You can mark the start of Styles’ more heavily-patterned days with his black-and-red striped suit from Lanvin. This double-breasted suit was the first of many, but what I really love about this look is the long hair paired with it. Goodbye, floppy, boyband hair. Hello, rock star Styles.

November 2015: Harry Styles Wears The Suit That Changed Everything

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While you now know that bold print, flared pants, and a Gucci label are all staples in his wardrobe, Styles’ floral suit from the 2015 American Music Awards was a watershed moment in his fashion history. This bold suit absolutely broke the internet and became the model of his future aesthetic. It also began his long-term friendship with Gucci’s creative director Alessandro Michele. In fact, when Styles wore this floral suit, Michele was only newly at the helm of Gucci and Styles became the first person to take one of Michele’s runway designs to the red carpet.

September 2017: Harry Styles’ First Floral Gucci Suit

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Following the drop of his first solo album, Styles stepped out on his first solo tour in ‘fits that majorly departed from his One Direction days. For his tour’s very first performance on Sept. 19, 2017, he wore a floral Gucci suit. The tailored, embroidered look is a far cry from the white T-shirts and jeans of yesteryear.

September 2017: Harry Styles Goes Retro

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Although suits were his thing in 2017, the Gucci look Styles wore for the 2017 iHeartRadio Music Festival was his biggest fashion risk to date. The harlequin number, featuring wide-leg pants, overwhelming amounts of argyle, and a voluminous pussy bow, was proof that Styles was willing to step way outside of the box — with Michele’s seal of approval, of course.

September 2017: Harry Styles’ Gucci Suits On Tour 2.0

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Styles’ Suit Party of 2017 continued with this tailored, satin number. Before you ask, yes, it’s Gucci. All of his suits at the time show Styles was beginning to challenge menswear fashion expectations. This red satin suit is bold and floral, but the cut still adheres to standard menswear tailoring. It’s fun and different, but there’s so much more boundary-breaking to come.

May 2019: Harry Styles’ Met Gala Moment

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For his first-ever appearance at the Met Gala in May 2019, Styles wore — shocker — Gucci, but there’s a newly minted androgynous feel to this look. The sheer top, puffy sleeves, and frills are all more aligned with what’s considered traditionally feminine, while his visible tattoos and tuxedo trousers are considered traditionally masculine. The blend of the two is pure fashion goodness.

December 2019: Harry Styles’ “Canadian Tuxedo”

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The Canadian tuxedo is a time-honored celebrity classic, but Styles’ put his own twist on the look during a 2019 performance. This custom Archie Alled-Martínez set was designed to look like a denim shirt tucked into jeans, but is actually made out of knitwear, plus a whole lot of sparkle.

February 2020: Harry Styles’ Pearlcore Moment

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Styles’ continued to explore androgynous fashion in 2020. As a result, that was the year that all of his fans became obsessed with pearl necklaces. It’s such a simple accessory, but when he appeared at the 2020 Brit Awards in February, the addition of a single strand of pearls under his white collar popped against the purple sweater vest. Styles’ stylist Harry Lambert called the aesthetic “granny chic.”

February 2020: Harry Styles Lights Up The Stage

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When it comes to memorable looks, Styles’ 2020 Brit Awards performance look is a standout. This Gucci set included wide-leg pants, a matching shirt, suspenders, and gloves. It was overflowing with details — lace, sequins, stoning, you name it. Just when you think he can’t do anything more exciting or unexpected, Styles is more than prepared to prove you wrong.

March 2021: Harry Styles’ Gets Playful At The Grammys

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Styles’ look from the 2021 Grammy Awards encapsulates every fun element the singer likes to experiment with. First off, texture. He’s got on a tweed blazer, a knit sweater vest, corduroy pants, and a feathered boa, all in vastly different colors. It’s a look that breaks nearly every fashion rule, and doesn’t Styles look so happy doing it?

May 2021: Harry Styles Goes Full ‘70s

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Over the years, Styles’ prints have only gotten more intense and eccentric. Case and point: the brown, orange, and cream suit he wore to the 2021 Brit Awards. The rectangle pattern looks like the coolest upholstery in a ‘70s dream house (no offense).

April 2022: Harry Styles Channels His Inner Disco Diva

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Headlining Coachella is a time for musicians to go all-out with their looks and Styles didn’t disappoint when he took the stage in April 2022. The rainbow paillettes on this Gucci jumpsuit glittered blindingly and the cut was super androgynous.

May 2022: Harry Styles’ Neon Candy Cane Moment

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Styles’ jumpsuit from a May 2022 performance on Today is beyond words. Yo Gabba Gabba! was the first thing that came to my mind followed by, dang, I love those bell sleeves. This ‘fit is fun and a tad bit retro, and Styles looked like he was having the best time wearing it.

September 2022: Harry Styles’ HA HA HA Debut

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Talk about a full-circle moment. Seven years after first rocking Michele’s designs, Styles and Michele announced a collaborative, forthcoming Gucci collection: Gucci HA HA HA. The singer previewed some of its pieces at a Don’t Worry Darling photocall during the 2022 Venice Film Festival. His white pinstripe suit, ‘70s style ascot, and flared navy pants are all, by now, associated with his vibe.