42 of the most daring outfits Harry Styles has ever worn

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  • Harry Styles is a man of many talents, but he's also known for his bold fashion choices.

  • In the 13 years since he was on "The X Factor" as part of One Direction, he's become a fashion icon.

  • To celebrate his 29th birthday, here are his wildest outfits.

Harry Styles let us know early on to expect bold sartorial choices when he was spotted on the streets of London in a onesie and skater sneakers in 2010.

harry styles 2010
Harry Styles from One Direction in Covent Garden on November 10, 2010 in London, England.Neil Mockford/FilmMagic/Getty Images

At the time, he was just a 16-year-old kid competing in "The X Factor" alongside the four other members of One Direction. They'd go on to place third.

To meet royalty in November 2014, Styles donned a leopard-print leather jacket. It's hard to tell who looks more starstruck.

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Kate Middleton meets Harry Styles at the Royal Variety Performance at the London Palladium on November 13, 2013.Yui Mok/WPA Pool/Getty Images

It's not the only time that a celebrity has gotten a little tongue-tied around the royals.

For One Direction's performance at the 2014 AMAs, Styles rocked a Sgt. Pepper-inspired military jacket.

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Harry Styles onstage at the 2014 American Music Awards on November 23, 2014.Jeff Kravitz/AMA2014/FilmMagic/Getty Images

Please note the leopard-print boots.

He arrived at 2014's British Fashion Awards in a bold striped suit, but it wouldn't be his last.

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Harry Styles attends the British Fashion Awards on December 1, 2014, in London.Mike Marsland/WireImage/Getty Images

He also started to let his hair grow out from bouncy curls.

Styles opted for a suit that almost looks like an optical illusion during a night out in London in September 2015.

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Harry Styles at Lou Lou's Club in London on September 21, 2015.Mark Robert Milan/GC Images/Getty Images

It was next in a long line of bold suits.

At the 2015 American Music Awards, the "Adore You" singer went for his most out-there look yet: a white floral suit with a bolo tie.

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Harry Styles of One Direction arrives at the 2015 American Music Awards on November 22, 2015.C Flanigan/Getty Images

He'd return to the patterned suit look more and more frequently as his career progressed.

During 2016, Styles essentially disappeared from the public eye, but he returned with a pink suit to promote his first solo single on "The Today Show" in May 2017.

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Harry Styles performs on NBC's "Today" at Rockefeller Center on May 9, 2017, in New York City.James Devaney/GC Images/Getty Images

Styles dropped "Sign of the Times" in April 2017, and solidified that his new music and fashion choices would be nothing like his days in One Direction.

We call this suit he wore to the Radio 1 Breakfast Show in May 2017 "picnic blanket chic."

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Harry Styles arriving at BBC Broadcasting House in London ahead of an appearance on The Radio 1 Breakfast Show with Nick Grimshaw.Jonathan Brady/PA Images/Getty Images

Don't forget the loafers — a perfect touch.

The "Kiwi" singer was spotted leaving a secret gig in London wearing purple silk pants with embroidered dragons in May 2017.

harry styles may 2017
Harry Styles leaving a secret gig at the Garage in Islington on May 13, 2017, in London.GORC/GC Images/Getty Images

Styles also started wearing rings and other accessories.

Just a few days later in NYC, Styles again wore dragon-printed pants, but this time as part of a mauve suit with a peach-colored shirt.

harry styles may 2017
Harry Styles poses for SiriusXM from the Roxy Theatre on May 17, 2017 in West Hollywood, California.Emma McIntyre/Getty Images for SiriusXM

He was single-handedly bringing back the Ed Hardy aesthetic.

This jacket may remind you of your grandma's couch, but he made it work at a show in September 2017.

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Harry Styles performs onstage at the Greek Theatre on September 20, 2017.Jeff Kravitz/FilmMagic for Sony Music/Getty Images

He'd wear this suit again in the music video for "Kiwi."

He broke out another eye-catching suit at the iHeartRadio Music Festival in September 2017.

harry styles iheart 2017
Harry Styles attends the 2017 iHeartRadio Music Festival at T-Mobile Arena on September 22, 2017, in Las Vegas, Nevada.David Becker/Getty Images for iHeartMedia

His shirt features what's called a lavallière. He'd come back to these frequently.

At a performance at Radio City Music Hall in September 2017, the pop star donned a red-and-black floral suit.

Harry Styles Live On Tour - New York
Harry Styles performs onstage at Radio City Music Hall on September 28, 2017, in New York City.Kevin Mazur/Getty Images for Sony Music

He rocked the loafers again, as well.

He brought Halloween vibes to an October 2017 show with his orange suit and black blouse.

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Harry Styles performs during the CBS Radio Presents 5th Annual "We Can Survive" Show at the Hollywood Bowl on October 21, 2017.Timothy Norris/Getty Images

The following year, he dressed up as Elton John for Halloween, and even got approval from the legend himself.

This metallic paisley suit Styles wore to the 2017 ARIA Awards in November is an all-time great look.

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Harry Styles arrives for the 31st Annual ARIA Awards 2017 at The Star on November 28, 2017, in Sydney, Australia.Scott Barbour/Getty Images for ARIA

As per usual, be sure not to miss his shoes — in this case, metallic copper square-toed boots.

During his concert in Copenhagen in March 2018, Styles channeled Elvis with this shiny, powder blue suit.

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Harry Styles performs a live concert at Royal Arena in Copenhagen on March 19, 2018.Gonzales Photo/Bo Kallberg/PYMCA-Avalon/Universal Images Group/Getty Images

Also making an appearance, another bow shirt.

Not since the 1970s have bell-bottoms looked this good. Styles wore this suit for his performance at Madison Square Garden in June 2018.

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Harry Styles performs onstage at Madison Square Garden on June 21, 2018.Kevin Mazur/Getty Images for HS

According to Fashionista, the Gucci suit had the French phrase "jardin d'hiver" embroidered around some bouquets of flowers. Jardin d'hiver means "winter garden" in French — perhaps a nod to the iconic venue?

To induct his friend and mentor Stevie Nicks into the Rock & Roll Hall of Fame in March 2019, Styles opted for a royal blue corduroy suit and white boots.

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Harry Styles and Inductee Stevie Nicks pose at the 2019 Rock & Roll Hall Of Fame Induction Ceremony on March 29, 2019.Dia Dipasupil/FilmMagic/Getty Images

In the past couple of years, he's swung from skin-tight skinny jeans to bell-bottoms, flares, and generally loose clothing.

Styles co-chaired the 2019 Met Gala in May and rocked a black jumpsuit with a sheer top and a single pearl earring.

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Harry Styles attends The 2019 Met Gala Celebrating Camp: Notes on Fashion at Metropolitan Museum of Art on May 6, 2019.Dia Dipasupil/FilmMagic/Getty Images

His shirt features what's called a lavallière. He'd come back to these frequently.

He was spotted out in New York City while rehearsing for "Saturday Night Live" in November 2019 in this fuzzy sheep sweater, pinstriped pants, and pink loafers.

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Harry Styles seen out and about in Manhattan on November 12, 2019, in New York City.Robert Kamau/GC Images/Getty Images

The sweater, designed by Lanvin, had some people comparing his look to an iconic outfit worn by Princess Diana in the '80s.

While performing on "SNL," he experimented with a monochromatic look.

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Musical guest Harry Styles performs "Watermelon Sugar" on November 16, 2019.Will Heath/NBC/NBCU Photo Bank/Getty Images

He rocked a very "Watermelon Sugar"-esque outfit to perform the song.

At Capital's Jingle Bell Ball in December 2019, Styles wore an extremely low-cut shimmery one piece.

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Harry Styles performs on stage during day one of Capital's Jingle Bell Ball.Isabel Infantes/PA Images/Getty Images

The man loves a jumpsuit.

At the 2020 BRIT Awards, Styles wore three distinct outfits. On the red carpet, he adopted a grandpa aesthetic.

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Harry Styles attends The BRIT Awards 2020 on February 18, 2020.Jim Dyson/Redferns/Getty Images

Once again, he accessorized with a string of pearls. He also paid homage to his ex-girlfriend Caroline Flack, who died a few days before, by wearing a black ribbon on his lapel.

To perform, he changed into a delicate lace jumpsuit.

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Harry Styles performs on stage during The BRIT Awards 2020 on February 18, 2020.Dave J Hogan/Getty Images

Styles wore a lace Gucci jumpsuit with matching gloves and suspenders to perform at the ceremony.

For an after-party, he changed once again into a canary yellow suit with a lavender shirt and lavallière.

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Roman Kemp and Harry Styles attend the Sony BRITs after-party at The Standard on February 18, 2020.Eamonn M. Mccormack/Getty Images for Sony

His pin reads "Treat People with Kindness," one of Styles' frequent phrases and a song from his 2019 album, "Fine Line."

We love Styles, truly, but this look at the "Today" show reminds us of a little kid playing dress-up in his dad's clothes.

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Harry Styles is seen performing at the "Today Show" on February 26, 2020.Jose Perez/Bauer-Griffin/GC Images/Getty Images

The wide brown polka-dot tie, bright blue shirt, brown pants, and pink jacket somehow work, but the ensemble is what we thought businessmen looked like when we were 9 years old.

Styles once again wore polka dots at a SiriusXM performance, this time as a sweater vest.

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Harry Styles performs for SiriusXM and Pandora in New York City at Music Hall of Williamsburg on February 28, 2020.Kevin Mazur/Getty Images for SiriusXM

His pants just keep getting looser and looser.

Styles made a rare appearance in jeans on "Today" at the end of February 2020.

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Harry Styles on Wednesday, February 26, 2020.Nathan Congleton/NBC/NBCU Photo Bank/Getty Images

Rarely do we see this particular pop star in a pair of blue jeans.

We'd be remiss if we didn't include at least one of the outfits from his December 2020 Vogue cover — Styles was the first-ever male Vogue cover star.

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Harry Styles in the December 2020 issue of Vogue.Tyler Mitchell/Vogue

Even though Styles clearly isn't the first man to ever rock a skirt or a dress, the internet kind of lost its mind about it. We think he looks iconic, as per usual.

On March 14, 2021, Styles performed at the Grammys for the first time, wearing a leather suit, lime green boa, and no shirt.

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Harry Styles poses for the 2021 Grammy Awards on March 14, 2021.Anthony Pham via Getty Images

That wouldn't be his only boa look, though.

... and to win his first-ever Grammy, Styles took to the stage in a checkered yellow jacket, brown cords, a pink V-neck sweater, and a new purple boa.

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Harry Styles attends the 63rd Annual Grammy Awards on March 14, 2021.Kevin Mazur/Getty Images for The Recording Academy

Styles became the first One Direction member to win a Grammy when he took home the statue for Best Pop Solo Performance for his song "Watermelon Sugar."

He brought out a third outfit (and third boa) for the press room after his win.

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Harry Styles at the 63rd Annual Grammy Awards Virtual Press Room broadcast.Amy Sussman/Getty Images for The Recording Academy

All three outfits were custom Gucci designed by Alessandro Michele, one of his longtime creative partners.

In May 2021, Styles once again brought out one of his boldest looks for the BRIT Awards, this time in a '70s patterned suit and matching purse.

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Harry Styles during the BRIT Awards 2021 on May 11, 2021.JMEnternational/JMEnternational for BRIT Awards/Getty Images

As usual, Styles rocked a Gucci suit for the red carpet.

The "Eternals" actor did not disappoint on his second tour, aptly titled Love on Tour. We're partial to the hot-pink fringed vest he wore at the Las Vegas show in September 2021.

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Harry Styles performs onstage during the tour opener for Love On Tour at MGM Grand Garden Arena on September 4, 2021.Anthony Pham/Getty Images

This was the first show of his tour, and we think he got the aesthetic perfect on the very first try.

Styles put on two Halloween shows in 2021 and wore two costumes. First up, his Dorothy Gale-meets-Strawberry Shortcake fit.

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Harry Styles performs onstage at Harry Styles "Harryween" Fancy Dress Party at Madison Square Garden on October 30, 2021.Theo Wargo/Getty Images for HS

Fittingly, he called the two shows "Harryween."

His second "Harryween" costume did not disappoint either.

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Harry Styles performs onstage during "Harryween" Fancy Dress Party at Madison Square Garden on October 31, 2021.Kevin Mazur/Getty Images for HS

The "Cherry" singer slayed in a harlequin clown costume for his second Halloween show.

During the first weekend of Coachella in 2022, Styles chose this rainbow, sequined jumpsuit to perform with country legend Shania Twain.

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Shania Twain performs with Harry Styles at the 2022 Coachella music festival.Kevin Mazur/Getty Images for ABA

He dramatically tore off a huge fuzzy coat to reveal this sparkling one-piece during his performance of "As It Was," his second No. 1 song.

He and Twain performed "Still the One" and "Man! I Feel Like a Woman" together.

For weekend two, he chose a hot-pink cowboy-inspired fit and a huge fuzzy pink coat.

Harry Styles performs on the Coachella stage
Harry Styles performs on the Coachella stage during the 2022 Coachella Valley Music And Arts Festival on April 22, 2022.Kevin Mazur/Getty Images for Harry Styles

You can't see it here, but his pants had his initials embroidered on the back in metallic silver letters.

For a 2022 performance on the "Today" show, Styles welcomed us all to "Harry's House" in a striped, long-sleeved one-piece that drew comparisons to a candy cane.

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Harry Styles performs on NBC's "Today" on May 19, 2022.Dia Dipasupil/Getty Images

"Well, it's early, so I wanted to be comfortable," told the "Today" show of his outfit. "I thought, sleeping bag, babygro, I'm going for comfort. And I thought I could soak up some of the rain with this."

During Radio 1's Big Weekend later that month, he wore a purple sequin jumpsuit.

Harry Styles performs on stage during Radio 1's Big Weekend
Harry Styles performs on stage during Radio 1's Big Weekend 2022 on May 29, 2022.Dave J Hogan/Getty Images

Styles added yet another jumpsuit to his growing collection during this performance, this time wearing a sleeveless black jumpsuit with stripes of purple sequins.

Styles walked the red carpet at the Venice Film Festival in a navy suit with exaggerated shoulders and a baby-blue shirt with a huge collar in September.

Harry Styles attends the "Don't Worry Darling" red carpet
Harry Styles attends the "Don't Worry Darling" red carpet at the 79th Venice International Film Festival on September 5, 2022.John Phillips/Getty Images

While we might all be more concerned with the behind-the-scenes drama of "Don't Worry Darling" and its premiere, we can't ignore Styles' perfect '70s-inspired Gucci suit and sunglasses that drew more than a few comparisons to Sir Elton John.

At the premiere of "My Policeman" in September, Styles wore pastel-green pants with a dark-green jacket and oversized flower on the lapel, and he carried a bright-green handbag.

Harry Styles arrives for the premiere of My Policeman during the Toronto International Film Festival in Toronto, Ontario, Canada, on September 11, 2022.
Harry Styles arrives for the premiere of "My Policeman" during the Toronto International Film Festival on September 11, 2022.GEOFF ROBINS/AFP/Getty Images

As usual, he was head-to-toe Gucci.

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