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These Harry Styles Looks Will Leave You on a Watermelon Sugar High

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If there’s anyone who knows how to walk the fine line of fashion, it’s Harry Styles.

Through the years, the One Direction alum has served up plenty of memorable looks both on and off the stage. Take the 2021 Grammys, where he walked the red carpet in a yellow plaid blazer—a piece reminiscent of Cher Horowitz’s wardrobe in Clueless—and a purple feather boa. When it was time to perform his smash hit “Watermelon Sugar,” Harry stole the show by swapping his ‘fit and going shirtless underneath a custom Gucci leather suit. 

“Clothes are there to have fun with and experiment with and play with,” he said of his sartorial approach in a 2020 Vogue cover story, in which he wore a dress in the accompanying photo spread. “When you take away ‘There’s clothes for men and there’s clothes for women,’ once you remove any barriers, obviously you open up the arena in which you can play.”

And with the 2023 Grammy Awards just around the corner, Harry—who is nominated for six awards, including Song of the Year for “As It Was” and Album of the Year for Harry’s House—is likely to turn heads once again in another fashion statement.

Ahead of this year’s ceremony, taking place at Los Angeles’ Crypto.com Arena on Feb. 5, relive all of Harry’s best looks.

Matt Winkelmeyer/Getty Images

Making a Statement

Harry added some color to his pinstriped suit in 2022 by rocking an eye-catching statement necklace. 

Dominique Charriau/WireImage

Simply Darling

For Don’t Worry Darling‘s big debut at the 2022 Cannes Film Festival, Harry rocked a structured navy suit with a light blue shirt featuring an oversized collar detail.

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Green Dream

Proving that he has fashion in the bag, Harry toted a green purse to the 2022 premiere of My Policeman.

Dia Dipasupil/Getty Images

Oh My Pearls

What’s in Harry’s House? A set of pearls, apparently.

Stephane Cardinale – Corbis/Corbis via Getty Images

Strike a Pose

Harry came dressed to impress for a Cannes Film Festival photocall in 2022.

Kevin Mazur/WireImage

Feeling Loose

Who said you can’t be comfy on the red carpet? The Don’t Worry Darling actor donned loose-fitting trousers and an oversized velvet jacket in 2022.

Karwai Tang/WireImage

Layered Look

Harry paired his burgundy suit with a purple sweater over a collared shirt at the 2020 BRIT Awards.

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Rockstar Vibes

The “Watermelon Sugar” singer channeled Elvis Presley in a low-plunging jumpsuit during Jingle Bell Ball 2019 in London.

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Nailed It

At the 2020 Gucci Cruise show, all eyes fell on Harry’s perfect pastel manicure.

Dimitrios Kambouris/Getty Images for The Met Museum/Vogue

Nothing to Hide

Jaws dropped when the singer arrived to the 2019 Met Gala in this sheer top from Gucci. 

Mike Coppola/WireImage

Bold in Blue

The One Direction star wore a blue velvet Gucci suit to the 2019 Rock & Roll Hall Of Fame Induction Ceremony.

Kevin Mazur/Getty Images

Stylin’ Styles

You can’t deny it…the man’s got swag, especially when sporting an orange-printed suit at Radio City Music Hall. 

Scott Barbour/Getty Images

Purple Rain

Harry was the prince of fashion performing at the 2017 ARIA Awards in this bold, paisley-printed purple metallic suit.

Jeff Kravitz/FilmMagic for Sony Music

Floral Phase

In late 2017, it was clear that the “Wild Thoughts” singer was going through a floral suit phase and we’re not complaining. 

David M Benett/Dave Benett/WireImage

Well Suited

The pop star cleans up nicely, wouldn’t you say? Harry wore a tailored-to-perfection double-breasted suit to the premiere of Dunkirk in 2017.

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Mr. Grey

He joined some of the world’s most beautiful supermodels at the 2017 Victoria’s Secret Fashion Show in a grey suit with a sleek pastel-green shirt underneath.

Jamie McCarthy/Getty Images

Keep It Classy

Harry attended the Dunkirk World Premiere in an impeccable Raf Simons-designed tuxedo jacket with a classic black dress shirt tucked into black slacks that were detailed with a red and white marching band embroidery on the hem.

Gareth Cattermole/Getty Images

Fashion Forward

How do men attract attention at fashion week? Hint: Take a peek at Harry’s leopard-print sweater worn at the Burberry Prorsum Womenswear Spring/Summer 2014 show.

Pascal Le Segretain/Getty Images

Pinned Down

Harry attended the 2014 British Fashion Awards in a red pin-striped suit that worked perfectly with his semi-groomed hair. 

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Coat Chic

Even when he’s not trying, the “Kiwi” singer looks cool. 

Olivia Salazar/WireImage

Casual Cool

In 2013, the boy bander rocked skinny jeans, boots and Ray-Ban sunglasses.

Stuart C. Wilson/Getty Images

Scarf It Down

When you win an award at the 2013 British Fashion Awards, it means your style perspective is strong. Also, when you can effortlessly sport a scarf to a big event, you definitely deserve cred. 

Mike Marsland/WireImage

Fresh Fashion

Harry’s love for fashion was noticeable even early on his career. This suit jacket and casual pants combo worked well for the Burberry runway show. 

Dave M. Benett/Getty Images

3-Piece Ensemble

Even at 18 years old, the British singer opted for a classy look with a three-piece suit—with a statement bow-tie—for the 2012 BRIT Awards.

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Prep Street

It’s true that Harry and the rest of his former band mates have come a long way style wise, but back in 2012, the part-casual, part-formal outfit combo did it for fans. 

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Hair Envy

Perhaps it’s his voluminous hair or dark sunglasses, but the simple tee and pants look on Harry back in 2012 was so freaking cool.

Watch the 2023 Grammy Awards Sunday, Feb. 5, at 8 p.m. ET/5 p.m. PT on CBS and don’t miss E! News the next day at 11 p.m. for a full recap of music’s biggest night.

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