Photo: Daniele Venturelli/WireImage ; JMEnternational/JMEnternational for BRIT Awards/Getty ; Dimitrios Kambouris/Getty
Harry Styles' fashion sense is incredibly unique.
Whether he is sporting feather boas on stage or statement suits on the red carpet, the “Watermelon Sugar” singer always delivers out-of-the-box looks. However, the multi-hyphenate star’s wardrobe wasn’t always this way: During the early days of his career withOne Direction, he was often clad in plain white tees and skinny jeans.
A budding style icon, the pop star founded hisown beauty brand, Pleasing, in 2021 and was the first man toland a solo coverofVoguethe previous year. Styles told the outlet that he views fashion as another way to express himself, embracing gender-fluid garments that feed his creativity.
“Clothes are there to have fun with and experiment with and play with. What’s really exciting is that all of these lines are just kind of crumbling away,” he said. “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.”
While the star has developed a signature retro style, often turning to brands like Gucci for custom looks, he’s likely to continue to surprise us with his eye-catching ensembles. Keep reading for a look back at some of Harry Styles' best outfits.
Harry Styles at the BBC Radio 1 Teen Awards in 2011
Dave Hogan/Getty
Fresh off the release of their first single, “What Makes You Beautiful,” One Direction hit the red carpet at the 2011 BBC Radio 1 Teen Awards in coordinating outfits. Styles wore his signature look at the time: a white button-down shirt, a grey blazer with a red pocket square, a matching bow tie, grey pants and white sneakers.
Harry Styles at the BRIT Awards in 2012
One Direction.Dave M. Benett/Getty
Styles attended the 2012 BRIT Awards with his fellow band members wearing matching suits. Taking home the award for best British single, the pop singer kept it classic in a grey three-piece suit, which he accessorized with a black bow tie, matching pocket square and dress shoes.
Harry Styles at the VMAs in 2012
Steve Granitz/WireImage
One Direction made their VMAs debut in 2012, once again putting a modern twist on traditional menswear. Styles walked the red carpet in a speckled grey blazer and vest, which he paired with a white button-down shirt, black skinny jeans and a red polka-dot pocket square.
Harry Styles at theOne Direction This Is Uspremiere in 2013
Dave M. Benett/WireImage
Starting to get a bit more playful with his style, the star attended the London premiere of his concert film,One Direction This Is Us, donning a black button-down shirt with white hearts. He kept the rest of the look simple with a black blazer, skinny jeans and ankle boots.
Harry Styles at the Teen Choice Awards in 2013
Taking a break from classic suits, Styles showed off his chest tattoos at the 2013 Teen Choice Awards in a loosely-buttoned white shirt. His casually cool ensemble also consisted of black skinny jeans, a brown belt, black ankle boots and a tan wide-brimmed hat.
Harry Styles at London Fashion Week in 2013
Gareth Cattermole/Getty
Harry Styles at the British Fashion Awards in 2013
Stuart C. Wilson/Getty
Styles attended the 2013 British Fashion Awards in another bold shirt choice: a black sheer button-down. He finished off the monochromatic look with skinny jeans, a blazer, ankle boots and a patterned scarf.
Harry Styles at the BRIT Awards in 2014
One Direction.David M. Benett/Getty
Keeping it consistent, Styles donned his favored skinny jeans, a patterned shirt and a blazer for the 2014 BRIT Awards. His lace button-down shirt had a skull embroidered on the chest, which added some edge to the look.
Harry Styles at the AMAs in 2014
Axelle/Bauer-Griffin/FilmMagic
It was all about the accessories for the pop singer’s look at the 2014 AMAs. His leopard print boots and wide-brimmed hat perfectly complemented the simple all-black ensemble, which included a tunic shirt and blazer with embellished collars.
Harry Styles at the British Fashion Awards in 2014
Mike Marsland/WireImage
Harry Styles onGood Morning Americain 2015
Stephen Lovekin/Getty
For his performance onGood Morning Americain August 2015, Styles wore a silk Saint Laurent bomber jacket in an animal print. While the jacket was a statement piece, he stuck to a simple vibe for the rest of his ensemble with black skinny jeans, ankle boots and silver rings.
Harry Styles walking in London in 2015
Mark Robert Milan/GC Images
Styles was spotted in London in September 2015 wearing a bold tailored suit. The retro-inspired look included an intricately patterned jacket and slim-cut pants, which he chose to accessorize with a plain black shirt, ankle boots and silver rings.
Harry Styles at the AMAs in 2015
Kevin Mazur/AMA2015/WireImage
Harry Styles on theTODAYshow in 2017
James Devaney/GC Images
After a brief hiatus from the spotlight, Styles embarked on his solo career, sporting shorter locks and even bolder ensembles. The star performed his debut single, “Sign of the Times,” on theTODAYshow in May 2017, wearing a hot pink suit over a black dress shirt. He accessorized the bright suit with black boots and chunky silver jewelry.
Harry Styles at BBC Radio in 2017
Jonathan Brady/PA Images
Styles loves a patterned suit on and off the red carpet. The singer arrived at BBC Radio for an appearance onThe Radio 1 Breakfast Show with Nicholas Grimshawin May 2017 wearing a red-and-white plaid suit. He finished off the “picnic chic” look with black loafers, a cross necklace and silver rings.
Harry Styles at theDunkirkpremiere in 2017
Harry Styles at the iHeartRadio Music Festival in 2017
David Becker/Getty
Dressed in head-to-toe Gucci, Styles embraced his rockstar status for his performance at the iHeartRadio Music Festival in September 2017. The designer suit included a black-and-red diamond pattern throughout, which he offset with a white pussy-bow blouse for a bold yet regal performance look.
Harry Styles onstage in New York City in 2017
Kevin Mazur/Getty
The Pleasing founder donned a custom Gucci look once again for his concert at Radio City Music Hall in September 2017. He paired his red floral suit with more classic accessories — a black pussy-bow blouse and loafers.
Harry Styles at the ARIA Awards in 2017
Scott Barbour/Getty
Harry Styles onstage in New York City in 2018
Harry Styles onstage in Paris in 2018
Helene Marie Pambrun via Getty
The pop star lit up the stage in the “City of Lights,” wearing another custom Saint Laurent suit that sparkled from top to bottom. He left the jacket open to reveal a low-cut ruffled blouse, which he accessorized with a cross necklace and an assortment of silver rings.
Harry Styles at the Rock & Roll Hall of Fame Induction Ceremony in 2019
Kevin Kane/Getty
The “Fine Line” singer opted for a royal blue corduroy suit to induct his friend and mentor,Stevie Nicks, into the Rock & Roll Hall of Fame in March 2019. He kept his accessories minimal, sporting white boots, silver rings and a low-cut white undershirt.
Harry Styles at the MET Gala in 2019
Dimitrios Kambouris/Getty
“I think everyone was expecting Harry to be in sequins, bright colors and a crown, but we decided on a different type of ‘camp’ that hopefully would surprise,” Harry Lambert, the star’s stylist,toldBritishVogue. “After such a colorful tour wardrobe it is nice to do something a little unexpected. This look is about taking traditionally feminine elements like the frills, heeled boots, sheer fabric and the pearl earring, but then rephrasing them as masculine pieces set against the high-waisted tailored trousers and his tattoos. The look, I feel, is elegant. It’s camp, but still Harry.”
Lambert also shared that Styles pierced his ears for the gala after the stylist spotted the pearl earrings on Gucci’s website a few days before the event.
Harry Styles walking in New York City in 2019
Robert Kamau/GC Images
Styles adopted a preppier style during a night out in N.Y.C. in November 2019. The star kept it cozy in a Lanvin navy-and-white sheep-printed sweater layered over a striped button-down shirt. He completed the mixed pattern look with navy pinstripe pants and light pink loafers.
Harry Styles at BBC Radio 1 in 2019
Neil Mockford/GC Images
In a fashion-savvy move, Styles rocked a shirt monogrammed with his name for a performance at the BBC Radio 1 studio in December 2019. The white band t-shirt, which had ‘Harry Styles’ written in a red heart, was from his collaboration with Gucci’s Alessandro Michelle. He styled the piece with brown high-waisted trousers, a plaid jacket, white sneakers and a pearl necklace.
Harry Styles in London in 2020
Far from his days of skinny jean ensembles, Styles was seen leaving BBC Radio 2 sporting a pair of corduroy wide-leg pants and a green embroidered jacket. He tied the whole look together with a brown striped T-shirt, a pearl necklace and bright red nail polish.
Harry Styles at the BRIT Awards in 2020
Joe Maher/Getty
Styles brought a “grandpa-chic” aesthetic to the 2020 BRIT Awards red carpet in a masterfully layered ensemble. The singer wore a dark brown Gucci suit over a purple sweater and blue dress shirt with an oversized white collar. His accessories, a pearl necklace and black Mary Jane shoes, only added to the vintage vibe of the look.
Harry Styles at a BRIT Awards afterparty in 2020
Neil Mockford / Ricky Vigil M/GC Images
Harry Styles in New York City in 2020
Harry Styles at SiriusXM Studios in 2020
Dia Dipasupil/Getty
Styles brought back his signature string of pearls for a visit to the Sirius XM Studios in N.Y.C. in March 2020. Sporting head-to-toe Gucci, the singer wore a navy blue sweater over a light blue shirt with a scalloped collar, electric green pants and white shoes.
Harry Styles at the 63rd Annual Grammy Awards in 2021
Taking home his first Grammy for “Watermelon Sugar,” Styles made his mark on the red carpet in a vintage-inspired ensemble. Dressed in custom Gucci, the singer wore a yellow checkered blazer, a striped V-neck sweater vest, brown corduroy pants and yellow-heeled boots. The most eye-catching detail was the purple feather boa he donned to top off the look.
Harry Styles performing at the 63rd Annual Grammy Awards in 2021
Kevin Winter/Getty
Harry Styles at the BRIT Awards in 2021
JMEnternational for BRIT Awards/Getty
Harry Style onstage in Las Vegas in 2021
Anthony Pham/Getty
Styles opened his first night of the Love On Tour concert series with a bang. Turning to his go-to brand Gucci, the “Adore You” singer shined in custom hot pink trousers and a vest with fringe detailing for a bold and whimsical performance look.
Harry Styles performing at Coachella in 2022
He finished off the playful look with an oversized pink fur coat and silver boots.
Harry Styles at the 79th Venice International Film Festival in 2022
Kate Green/Getty
The budding actor attended theDon’t Worry Darlingpremiere at the Venice Film Festival wearing a ’70s-inspired suit from hisGucci HA HA HA collection. The navy double-breasted suit featured exaggerated shoulders and was layered over a light blue shirt with an elongated collar. He styled the look with white boots, oversized sunglasses and chunky rings.
Harry Styles at the Toronto International Film Festival in 2022
Amy Sussman/Getty
Harry Styles at aDon’t Worry Darlingphotocall in 2022
A frequent wearer of pinstripe trousers, Styles donned a navy pair at a photocall forDon’t Worry Darlingin September 2022. He sported the Gucci garment with a navy velvet double-breasted blazer, blue collared shirt and black boots.
Harry Styles at theMy Policemanpremiere in 2022
Trading in vintage silhouettes for modern tailoring, Styles showed up at the Los Angeles premiere ofMy Policemanin a chic black Gucci suit. The minimalist ensemble consisted of a mandarin collar jacket, slim-cut pants, a gold statement belt and black glossy boots.
Harry Styles at the65th Annual Grammy Awards in 2023
Getty
Styles walked thered carpet at the Grammysin a rainbow patchwork Egonlab jumpsuit, which was covered in Swarovski crystals. He paired the one-piece with white shoes and gold jewelry.
The outfit showed off many of Styles' tattoos, as the square neckline dipped below Styles' chest.
source: people.com
