The 38 wildest outfits Harry Styles has worn over his decade-long career

Gabbi Shaw
·13 min read
harry styles
Styles at the BRIT Awards. Samir Hussein/WireImage/Getty Images
  • Harry Styles is a man of many talents, but he's also known for his bold fashion choices.

  • In the decade since he appeared on "The X Factor" as part of One Direction, he's become a fashion icon, worked with Gucci on ad campaigns and a fragrance, and even co-chaired the Met Gala in 2019.

  • To celebrate him becoming the first male solo cover star in Vogue history, we've picked 38 of his wildest outfits over the last 10 years.

  • Visit Insider's homepage for more stories.

Harry Styles rose to fame a full 10 years ago as a 16-year-old singer joining the newest boy band on the block, One Direction. The rest, as they say, is history.

But over the years, Styles has proven himself to be more than a teen idol. He's released two critically and commercially successful albums, starred in a Christopher Nolan film, collaborated with Gucci, and became a bona fide fashion icon.

And this December, Styles broke the internet when he was named Vogue's cover star, the first solo male cover in the magazine's history. To celebrate, we've chosen 38 of his truly wildest outfits, from extreme bell-bottoms to gingham suits — and who could forget the sheep sweaters?

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.

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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 One Direction. They'd go on to place third.

Two years later, One Direction had essentially conquered the world ... and were coordinating their outfits.

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Niall Horan, Liam Payne, Harry Styles, Zayn Malik, and Louis Tomlinson of One Direction. Scott Barbour/Getty Images

While his bandmates kept it simple, Styles opted for a baby blue jacket, bow tie, and Converse at the 2012 Logie Awards.

He was quickly making it known that he was the bold fashion risk-taker of the group.

At this point in his style evolution, Styles would frequently go for a bold print, like this heart shirt at the premiere of One Direction's movie, "This Is Us," in August 2013.

One Direction: This Is Us - World Premiere - Red Carpet Arrivals
Harry Styles and Niall Horan of One Direction. Karwai Tang/WireImage/Getty Images

Even though he was always down for a printed top, Styles mainly stuck to black skinny jeans. That would soon change.

His look at the 2014 BRIT Awards showed he had a bit of an edge to him — did you notice the skull in the center of his shirt?

Harry Styles attends The BRIT Awards
Harry Styles attends the BRIT Awards on February 19, 2014. Karwai Tang/WireImage/Getty Images

One Direction took home the award for British Video of the Year for "Best Song Ever" and the Global Success Award.

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.

When he walked the red carpet of the American Music Awards in 2014, he experimented with an accessory that would soon become a favorite — a fedora.

Harry Styles - American Music Awards 2014
Harry Styles American Music Awards 2014 Los Angeles, CA November 24, 2014 Kurt Krieger/Corbis/Getty Images

The embellished collar is also a sign of things to come — although in 2020, he rarely wears an all-black ensemble like this.

For their 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.

At the Capital FM Summertime Ball in June 2015, he went for an informal vibe, with a half-unbuttoned shirt and loose scarf/tie situation.

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Harry Styles of One Direction attends the Capital FM Summertime Ball at Wembley Stadium on June 6, 2015. Karwai Tang/WireImage/Getty Images

Again, Styles wore a loud print, boots, and black skinny jeans.

When the band performed on "Good Morning America" in August 2015, Styles went for a silk bomber jacket with an animal design.

One Direction Performs On ABC's "Good Morning America"
Harry Styles of One Direction performs during ABC's "Good Morning America" on August 4, 2015, in New York City. Kevin Mazur/WireImage/Getty Images

The jacket is Saint Laurent and retailed at the time for $2,690, according to GQ.

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.

He tried out a pair of bolder, more loose-fitting pants at a performance on "Jimmy Kimmel Live!" in November 2015, a trend he continues to rock to this day.

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Harry Styles of the band One Direction is seen performing on "Jimmy Kimmel Live" on November 19, 2015. RB/Bauer-Griffin/GC Images/Getty Images

The band had just released their final — for now — album, "Made in the AM." It was clear that Styles and the rest of the band were all itching to branch out, both musically and stylistically.

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 bright 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.

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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.

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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 solo tour in March 2018, he wore a sparkly suit on stage for a performance in Paris.

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Harry Styles performs during his European tour at AccorHotels Arena on March 13, 2018, in Paris, France Handout/Helene Marie Pambrun/Getty Images

As you'll see, Styles pulled out all the stops for his first solo tour.

A week later, during his concert in Copenhagen, 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.

Next up, in Oslo, Styles experimented with a patchwork-esque suit.

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Harry Styles performs a live concert at Oslo Spektrum in Oslo, Norway, on March 21, 2018. Gonzales Photo/Tord Litleskare/PYMCA/Avalon/Universal Images Group/Getty Images

He kind of looks like a rag doll, but we like it.

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 during Harry Styles: Live On Tour — New York at Madison Square Garden on June 21, 2018, in New York City. 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

In fact, Styles got his ear pierced just for the occasion.

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.

At Capital's Jingle Bell Ball, 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.

In one of his last appearances of 2019, to host "The Late Late Show," Styles performed in a navy and red polka dot suit.

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Harry Styles guest-hosts "The Late Late Show with James Corden" on December 10, 2019. Terence Patrick/CBS/Getty Images

Styles began the promo cycle for "Fine Line" with typically bold choices, as seen here.

The very next day, the "Watermelon Sugar" singer popped up at a Spotify event wearing a cardigan that featured Babar the elephant.

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Harry Styles attends a Spotify private listening session for fans on December 11, 2019, in Los Angeles, California. Rich Fury/Getty Images for Spotify

According to Twitter, the cardigan is Lanvin and retails for a cool $1,365. You also may notice his string of pearls — they became big in 2020.

On Valentine's Day in 2020, Styles chose a bold green jacket with red and white stitching.

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Harry Styles leaving BBC Radio 2 on February 14, 2020, in London, England. Neil Mockford/GC Images/Getty Images

Unfortunately, this day was overshadowed by the news that he had been mugged at knifepoint later on that night.

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."

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 "The Today Show" at the end of February.

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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.

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