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 with One Direction, he was often clad in plain white tees and skinny jeans.
A budding style icon, the pop star founded his own beauty brand, Pleasing, in 2021 and was the first man to land a solo cover of Vogue the 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
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
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
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 the One Direction This Is Us premiere in 2013
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
Styles’ appearance at the Burberry Prorsum Womenswear Spring/Summer 2014 Fashion Show in September 2013 was one of his first notable fashion moments. While the star sported his usual black distressed skinny jeans and ankle boots, he dressed up the look with a leopard print shirt by the brand and a long black coat.
Harry Styles at the British Fashion Awards in 2013
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
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
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
The first of many patterned suits, the star coincidentally matched the red carpet at the 2014 British Fashion Awards in a red-striped double-breasted suit by Lanvin. He paired the striking garment with a black undershirt and ankle boots.
Harry Styles on Good Morning America in 2015
For his performance on Good Morning America in 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
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
Marking a clear shift in the star’s style, he walked the red carpet at the 2015 AMAs in a white floral suit by Gucci that included flared pants — a departure from his signature fitted silhouettes. He completed the look with a black bolo tie and ankle boots.
Harry Styles on the TODAY show in 2017
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 the TODAY show 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
Styles loves a patterned suit on and off the red carpet. The singer arrived at BBC Radio for an appearance on The Radio 1 Breakfast Show with Nicholas Grimshaw in 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 the Dunkirk premiere in 2017
Styles made a subtler fashion statement at the premiere of his first feature film, Dunkirk, in July 2017. While he chose a classic double-breasted suit by Gucci, the star couldn’t resist a pop of color. He topped off the look with red ankle boots that included gold embroidery on the sides.
Harry Styles at the iHeartRadio Music Festival in 2017
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
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
Continuing his streak of statement suits, Styles dazzled at the 2017 ARIA awards in a purple metallic suit with a paisley pattern by Alexander McQueen. The star also donned equally as eye-catching accessories, wearing a pair of gold chunky-heeled boots and silver rings on each hand.
Harry Styles onstage in New York City in 2018
Styles went full retro for the New York City stop of his 2018 tour, Harry Styles: Live On Tour, in a custom white floral suit by Saint Laurent. The ’70s-inspired look featured bell-bottom pants and oversized black lapels.
Harry Styles onstage in Paris in 2018
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
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
In an unforgettable MET Gala debut, Styles co-chaired the event rocking a custom look by Gucci. The all-black ensemble consisted of a frilly sheer blouse, high-waisted pants and heeled boots. He accessorized the gender-fluid look with his signature assortment of chunky rings, a polished manicure and one pearl earring.
“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, told British Vogue. “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
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
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
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
For his second look of the night, Styles switched from dark brown to bright yellow in a bold three-piece suit by Marc Jacobs. The pop star’s party look also featured a purple polka-dot shirt, a matching scarf and white loafers.
Harry Styles in New York City in 2020
A master class in mixing patterns: Styles donned a yellow-and-blue polka dot sweater vest by Lanvin over a white striped button-down shirt. Taking the patterned look one step further, he paired the bright sweater with navy-striped Lanvin trousers and red Gucci boots.
Harry Styles at SiriusXM Studios in 2020
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
Committing to his retro aesthetic, Styles sported another boa in a lime green hue for his opening performance of “Watermelon Sugar.” He kept the rest of his look simple, opting for a black leather suit by Gucci (sans undershirt) and matching heeled boots.
Harry Styles at the BRIT Awards in 2021
Styles stunned at the 2021 BRIT Awards in another custom look by Gucci. The color-blocked silk suit featured a double-breasted jacket and pleated flared pants – both in a brown macro-framed sequence print. The ensemble also included matching suede sneakers and a brown leather bag with a bamboo handle.
Harry Style onstage in Las Vegas in 2021
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
For his first weekend headlining Coachella in April 2022, Styles kept the glittering performance ensembles coming with this rainbow sequin jumpsuit by Gucci. He accessorized the disco-inspired outfit with black boots, a cross necklace and plenty of chunky rings, including two that spelled out his initials.
Harry Styles performing at Coachella in 2022
Styles took his performance look in a different direction for the second weekend of Coachella, opting for a cowboy-inspired ensemble. The hot pink vest and trousers set by Gucci included personal touches. The pants were embroidered with his initials while the vest was embossed with a cherry and strawberries — a nod to two songs on his album Fine Line, “Cherry” and “Watermelon Sugar.”
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
The budding actor attended the Don’t Worry Darling premiere at the Venice Film Festival wearing a ’70s-inspired suit from his Gucci 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
Styles wore another monochromatic look by Gucci to promote his second film of the year, My Policeman. The emerald green ensemble featured a double-breasted blazer with a silk flower brooch, light green pants and a matching bag.
Harry Styles at a Don’t Worry Darling photocall in 2022
A frequent wearer of pinstripe trousers, Styles donned a navy pair at a photocall for Don’t Worry Darling in September 2022. He sported the Gucci garment with a navy velvet double-breasted blazer, blue collared shirt and black boots.
Harry Styles at the My Policeman premiere in 2022
Trading in vintage silhouettes for modern tailoring, Styles showed up at the Los Angeles premiere of My Policeman in 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 the 65th Annual Grammy Awards in 2023
Styles walked the red carpet at the Grammys in 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.
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