You’ll Adore All of Harry Styles’ Best Looks

Harry Styles is simply golden at getting dressed. Take a look at some of the “Fine Line” singer’s best looks through the years.

By Kelly Gilmore Nov 19, 2022 2:00 PMTags
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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.

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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.

Making a Statement

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

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.

Green Dream

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

Oh My Pearls

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

Strike a Pose

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

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.

Layered Look

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

Rockstar Vibes

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

Nailed It

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

 

Nothing to Hide

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

Bold in Blue

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

Stylin' Styles

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

Purple Rain

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

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. 

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.

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.

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.

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.

Pinned Down

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

Coat Chic

Even when he's not trying, the "Kiwi" singer looks cool. 

Casual Cool

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

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. 

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. 

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.

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. 

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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