See Harry Styles’ Most Daring Looks Over the Years

Harry Styles, 2017 Victoria's Secret Fashion Show

Frazer Harrison/Getty Images for Victoria’s Secret

Harry Styles is set to co-host the 2019 Met Gala in just a few days!

The “Sign of the Times” singer will co-chair the major fashion event on May 6 alongside Lady Gaga, Serena Williams, Gucci creative director Alessandro Michele and Vogue‘s Anna Wintour. This honor is a nod to Styles’ growing presence in the fashion industry. Over the years, the 25-year-old has become known for his daring ensembles, on and off the stage.

So, as we continue counting down the days until the first Monday in May, we’re looking back at Style’s bold fashion choices, from metallic suits to leopard-print sweaters and beyond!

Let’s take a trip down fashion lane with the One Direction superstar’s must-see style moments!

Harry Styles, 2019 Rock & Roll Hall Of Fame Induction Ceremony

Mike Coppola/WireImage

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

ESC: Harry Styles, 2017

Kevin Mazur/Getty Images

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

ESC: Harry Styles

Scott Barbour/Getty Images

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

ESC: Harry Styles, 2017

Jeff Kravitz/FilmMagic for Sony Music

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

ESC: Harry Styles, 2017

David M Benett/Dave Benett/WireImage

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 and we say, “bravo!”

ESC: Harry Styles

Presley Ann/Patrick McMullan via Getty Images

The singer 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.

ESC: Harry Styles

Jamie McCarthy/Getty Images

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.

ESC: Harry Styles, 2014

Gareth Cattermole/Getty Images

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.

ESC: Harry Styles, 2014

Pascal Le Segretain/Getty Images

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

ESC: Harry Styles, 2014

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

ESC: Harry Styles, 2013

Olivia Salazar/WireImage

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

ESC: Harry Styles, 2013

Stuart C. Wilson/Getty Images

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. 

ESC: Harry Styles, 2012

Mike Marsland/WireImage

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

ESC: Harry Styles, 2012

Dave M. Benett/Getty Images

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.

ESC: Harry Styles, 2012

Peter Kramer/NBC/NBC NewsWire via Getty Images

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-suit outfit combo did it for fans. 

ESC: Harry Styles, 2012

Danny Martindale/Getty Images

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 E!’s Live From the Red Carpet: The 2019 Met Gala special on Monday, May 6 starting at 5 p.m. ET/ 2 p.m. PT! And don’t miss E! News Tuesday, May 7 at 7 p.m. for a full recap of fashion’s biggest night!

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