Harry Styles has a thing for retro, rock and roll-inspired suits, shirts, and trousers. For the chart-topping singer, no print is off-limits (especially if it’s of the floral variety), no pant is too flared, no heel is too high, and no nail will go unpolished. 

While Styles now favors Gucci’s nostalgia-fueled designs and Saint Laurent pieces with a bit of ’70s flair (think Freddie Mercury), the singer wasn’t always so fearless when it came to his fashion choices. Back in the early days of One Direction, the boy band member kept things fairly simple and classic, wearing more traditional polos, blazers, and sneakers. But  his closet has clearly evolved over the years, so much so we can easily spot when another celebrity starts dressing like him.

Basically, he went from boy-next-door to full-blown style icon.

Ahead, take a look at the singer’s fashion archive and evolution from preppy boy bander to fashion risk-taker and unofficial Gucci mascot.

RELATED: Harry Styles Randomly Wore the Same T-Shirt As Rachel Green From Friends 

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2011

2011

Harry showed off his layering skills during an appearance with his One Direction bandmates by popping both the collar of his blazer and the polo he wore underneath. 

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2011

2011

Before his wild, printed suits, Harry kept things simple with tailored pieces, including this prep-school blazer with white trim and an embroidered crest. 

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2013

2013

Every once in a while, you feel like going back to basics, even if you’re Harry Styles. The singer wore a classic white button-up shirt and black blazer to the New York premiere of One Direction’s film This Is Us.

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2013

2013

While promoting One Direction’s concert film This is Us, Harry spiced things up by adding a playful heart-printed shirt to his all-black outfit.

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2013

2013

Harry’s long-term relationship with leopard print pretty much began with the T-shirt he wore to the Burberry SS14 fashion show. 

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2013

2013

To accept his award for Style Icon of the Year, Harry showed up to the 2013 British Fashion Awards in a sheer button-up shirt, thin polka-dot scarf, and blazer. The vibe: prep school student with a Rolling Stones obsession.

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2014

2014

We’re dubbing the forest green, suede coat that Harry wore to Burberry’s fall 2014 fashion show the gateway into his preference for bold, loud, and printed ensembles. 

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2014

2014

At the 2014 American Music Awards, Harry went for a full-on, all-black rock and roll look with a wide-brimmed hat, embroidered tunic, and blazer.

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2014

2014

Practical and fashion-forward, Harry made his black Calvin Klein sweatshirt and skinny jeans combo less basic by tying a paisley- and skull-printed scarf around his floppy hair.

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2015

2015

Partially buttoned, oversized shirts in every print and color — such as this pink polka-dot option Harry wore while performing with One Direction at Apple Music Festival — have become an onstage and offstage staple for the singer.

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2015

2015

When it’s too warm out to wear a shearling coat, but too cool to go out in just a tee and skinny jeans, Harry throws on a fuzzy Saint Laurent vest.

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2014

2014

Proving that leopard print can be appropriate for any occasion (including hanging out with Queen Elizabeth II), Harry wore an animal-print jacket to attend the Royal Variety Performance with Britain’s royal family.

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2014

2014

Harry’s solution to never being too overdressed at the function: take a cue from Mick Jagger and wear a skinny scarf instead of a black tie.

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2015

2015

A silk embroidered Saint Laurent jacket is foolproof way to turn a T-shirt and jeans combo into something iconic.

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2015

2015

Solid and subtle? Nah. Harry wore a geometric, tailored Gucci suit to a Miu Miu party during London Fashion Week.

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2015

2015

The floral Gucci suit that Harry wore to 2015 American Music Awards may have launched a thousand memes, but we challenge you to find a sexier looking couch.

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2015

2015

File these black and white pinstripe pants under the running list of examples that when you’re Harry Styles, no trouser is too flared.

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2017

2017

For his debut solo Saturday Night Live performance, Harry went with something classic that provided just enough of a punch: a double-breasted, plaid Gucci suit. 

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2017

2017

Mastering the one-shoulder coat drape solidified Harry’s status as a street style star. The Gucci logo sweatshirt helped too (shop similar styles here).

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2017

TK

For his Today show performance, Harry swapped his beloved printed suits for a bright pink Edward Sexton option of every millennial’s dreams.

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2017

Harry Styles Fashion Victoria's Secret Fashion Show

At the Victoria’s Secret Fashion show, Harry melted the crowed (and the viewers watching at home) in a matchy, monochromatic blue-gray suit and button-down.

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2018

Harry Styles Fashion

During the European leg of his tour, the singer dazzled fans in Paris thanks to this sparkling suit — which is sort of reminiscent of the Eiffel Tower. Extra points for being on-theme!

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2018

Harry Styles Fashion

Obviously Harry likes the floral suits. He rocked this one on stage at Madison Square Garden during his 2018 tour. And why not pair a statement suit with a statement? Harry’s guitar was adorned with the words “end gun violence.”

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2019

Harry Styles Fashion

While dining in Soho, New York, the former boyband member was spotted wearing an electric blue, velvet suit over a white, scoop neck tee, styled with white boots. To finish off the look, he went with trendy polished nails and rings on almost every finger.

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2019

Harry Styles Fashion

When Harry co-hosted the 2019 Met Gala, he showed up wearing a very campy, ruffled sheer blouse and black trousers. The see-through nature of his top also allowed us a peek at his tats. We’re forever thankful for Camp.

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2019

Harry Styles Fashion

While out and about in the Big Apple, Harry layered a Princess-Diana-like blue sweater vest (embellished with sheep!) over a button-down and pinstripe pants, finishing off the look with light pink loafers.

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2019

Harry Styles Fashion

As he cracked jokes during his Saturday Night Live monologue, the star showed off some pale yellow trousers, a blue button down, and beige blazer. We have to say, his outfit wasn’t the only thing on point — that comedic timing was impeccable, too. Is there anything the man can’t do?

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2020

Harry Styles Fashion

Harry pulls off pearls better than we ever could. He paired the unlikely accessory with a blue sweater and scallop-collared shirt during a visit to the SiriusXM Studios. The bold green pants were another unexpected choice, but the man is clearly a fan color blocked outfits.

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2020

Harry Styles Fashion

Harry pulled out the pearls once again for the 2020 BRIT Awards. This favorite accessory of Harry’s is one of the better things to happen in 2020.

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2020

Harry Styles Fashion

While leaving BBC Radio 2 in London, the “Watermelon Sugar” singer gave us major ‘70s vibes with bell bottom corduroys and a light teal jacket. He completed the look with — you guessed it! — a pearl necklace.

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2020

Harry Styles Fashion

During a SiriusXM and Pandora performance in Williamsburg, Brooklyn, Harry once again gave us a lesson in layering, adding a polka-dot sweater vest over his button down and completing the look with pinstripe pants.

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