Yahoo LifestyleThe 38 wildest outfits Harry Styles has worn over his decade-long career
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.
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.
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.
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.
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?
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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."
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.
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.
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.
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.
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.
He rocked the loafers again, as well.
He brought Halloween vibes to an October 2017 show with his orange suit and black blouse.
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.
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.
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.
Also making an appearance, another bow shirt.
Next up, in Oslo, Styles experimented with a patchwork-esque suit.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
His pants just keep getting looser and looser.
Styles made a rare appearance in jeans on "The Today Show" at the end of February.
Rarely do we see this particular pop star in a pair of blue jeans.
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