You’ll Adore All of Harry Styles’ Best Looks

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No matter how many night changes come and go, Harry Styles‘ status as a style icon remains.

By the looks of his outfits through the years, the closet in Harry’s House must be incredible—and it’s likely Harry won’t disappoint with his ensemble for the 2022 American Music Awards on Nov. 20.

So, what is Harry’s method when it comes to fashion? Well, he pretty much throws all of society’s “rules” and gender norms out the window, which allows him to freely create.

“Clothes are there to have fun with and experiment with and play with,” Harry told Vogue in 2020. “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 play he does. Some of Harry’s most memorable outfits include the 2019 Met Gala, where he sported a sheer Gucci top paired with very high-waisted trousers. The ensemble is not one to be forgotten, though it differs quite a lot from another playful look Harry is famous for: His feather boa moment at the 2021 Grammys.

At the time, Harry stepped out on the Grammys red carpet in a yellow plaid blazer paired with a purple boa. The jacket was rather reminiscent of the ‘90s film Clueless—but it’s clear Harry very much has a clue when it comes to fashion.

And that’s not the only awards show Harry has made a lasting impression at. Back in 2015, the “She” singer made headlines for his flared-leg floral suit at the American Music Awards.

Now, Harry is set to attend the 2022 AMAs with nominations for Artist of the Year, Favorite Music Video and Favorite Pop Song. As for what he will wear this year? Only time will tell when the awards show kicks off Nov. 20.

In the meantime, keep scrolling to see some of Harry’s best looks through the years.


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.

Presley Ann/Patrick McMullan via Getty Images

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. 

Splash News

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.

Peter Kramer/NBC/NBC NewsWire via Getty Images

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. 

Danny Martindale/Getty Images

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.

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