When he shot to fame aged 16 as a runner-up on the X Factor, it was clear that Harry Styles wouldn't be playing by the rules of the traditional matchy-matchy boyband aesthetic. He fast showed he was the most directional dresser of the band, and charmed his way into the fashion world. By 2013 he'd won a British Fashion Award and he's since made a name for himself with his colourful aesthetic and flair for accessorising.
Now, as he turns 30, the singer has become a bona fide fashion boy, with a stake in the British brand SS Daley, a role as a Gucci ambassador and with music videos known as much as a who's-who of designers on the ascent, as they are for their catchy riffs.
The singer has many signature styles under his belt. In the early days, once he graduated from boyish hoodies and suit jackets worn with jeans, his aesthetic was inspired by Rolling Stones member Mick Jagger. He made Western boots, skinny scarves, unbuttoned Saint Laurent shirts and skin-tight jeans his staples, and was also a regular on the Burberry front row.
After he landed his first big movie role in Dunkirk he heralded in his Gucci era. In 2018 he became the face of then creative director Alessandro Michele's tailoring campaign, before he went on to collaborate on his own fashion line with the brand in 2022, titled Gucci HA HA HA.While the pandemic halted Harry's red carpet style and planned tour-drobe, his colourful music video looks for Watermelon Sugar and Golden proved his commitment to experimental looks and prints.
His commitment to playful style came into its own on his Love On Tour world dates which in spite of stretching over two years, never failed to surprise and delight his fans.
Here's Harry's style evolution in 30 looks.
Before Harry began to carve out his own style from the rest of the boys, he wore a grey three-piece suit for his first Brit Awards in 2012 — it was a far cry from his now colourful tailored looks.
When Harry had ushered in his Jagger era with a series of Saint Laurent looks, he took home a British Fashion Award in 2013.
At the world premiere for the One Direction movie a heart print Burberry shirt was the first nod to a print which has become a mainstay on his Love On Tour dates.
Harry's penchant for print continued to shine through in Burberry as he sat front row at Christopher Bailey's Spring 2014 show in leopard.
At the 2014 BFAs, Harry's hair had hit shoulder length and the suits were more daring, as he chose a double breasted red pin stripe style.
At the American Music Awards in 2015, a floral flared suit was one of his first red carpet forays away from the skinny cut.
To film his first major movie, Dunkirk, Harry's signature curls had been cut short and it matched a sharp new era for his style. He wore a sleek Raf Simons for Calvin Klein suit with a Western yoke detail on the trousers and steel-cap boots to the film's New York premiere.
At the iHeartRadio Music Festival in 2017, Harry confirmed he was in his Gucci era in a harlequin print suit and ruffle white blouse.
Having cemented himself as a Gucci muse after fronting one of Alessandro Michele's campaigns, the 2019 Met Gala with the theme Camp: Notes On Fashion saw Harry styled by the designer. He wore a custom sultry, sheer lace blouse and wide-leg trousers with patent block heels and a single pearl earring. It was simple yet considered subversive for breaking of gender norms.
To celebrate the release of Fine Line, Harry performed for fans in a kitsch silk fronted cardigan and what had become his signature accessories: a string of pearls, lashings of silver rings and a dark manicure.
Another event, another Gucci look. For the 2020 Brit Awards a plum coloured suit was contrasted with a marl knit, and blue shirt with a broderie anglaise collar.
Later that same night Harry had audiences in the palm of his hands, singing Fallen in a custom ivory lace shirt and high waisted trousers with floral embroidery, by Gucci (who else?).
A Today Show appearance which aired just before lockdown in 2020 saw Harry wear a patchwork JW Anderson cardigan. It went on to have a viral moment during the pandemic as TikTokers clamoured to crochet their own at home.
While Harry's tour had to be postponed during lockdowns, his videos became his stage. In scenes for Golden he wore a dress shirt and floral trousers both by newly graduated Steven Stokey-Daley, catapulting the designer to fame.
Harry Styles was the December 2020 cover star of Vogue US, wearing a Gucci shirred gown and black blazer shot by Tyler Mitchell.
This Harris Reed look inside the magazine was equally worthy of virality. The Brit designer crafted the smoking jacket and skirt constructed from tulle and pink satin worn over hoop skirt in less than a week. "I literally didn’t sleep. I’ve never made something faster in my entire life,” Reed said of the iconic look.
At the 2021 Grammys, Harry's latest Gucci garb channeled a Clueless' aesthetic with a texture-heavy combo of striped knit, plaid suit jacket, velvet trousers and a feather boa for good measure.
At the Brits in 2021 Harry's check print flared suit and bamboo handle Gucci 1947 Mini Bag were dressed down a touch with the Adidas Sambas poking out from his flares. He may have something to do with the shoes subsequent sell-out status.
A striped JW Anderson look was adapted into a wide-leg all in one for a performance for the Today Show in 2021. Vans trainers were his comfy footwear of choice for running around the stage.
For the Harryween event in Madison Square Gardens, the pop sensation wore a series of playful looks including this plaid blue dress.
At 2022's Venice Film Festival, Harry was promoting Don't Worry Darling and arrived in one of his Gucci HA HA HA looks; a pinstripe jacket worn over a white tank with navy trousers, accessorised with a neck scarf for some added flair.
Wearing another 1970s-look from his Gucci HA HA HA collection featuring an XL pointed collar, Harry proved that he's own best press.
For a Toronto Film Festival screening of queer love story My Policeman Harry wore expertly mismatched shades of green and his favourite Gucci 1947 Mini Bag.
A New York screening for Don't Worry Darling was another opportunity for some chic tailoring. This time nautical pinstripes and an asymmetric double breasted blazer.
As a performer and seven-time nominee at the 2023 Grammys Harry bought his best fashion game. He arrived in a plunging rainbow unitard by EgonLab, crafted from multi-coloured Swarovski crystal mesh.
While on stage Harry brought joy and movement in a silver fringed Gucci jumpsuit to perform As It Was. It was sartorial showmanship at its best.
Concluding his sparkling looks on the night, Harry scooped three Grammys gongs in a cropped tuxedo jacket, sequin chest-baring top and camel hued trousers.
Back on home soil, Harry walked the Brit awards red carpet in a Harris Reed black velvet suit with an oversized corsage as the designer had recently been appointed creative director at Nina Ricci.
On stage at the Brits, Harry wore a cropped, red, sequined jacket by Gucci over a a bare chest and navy tailored trousers. Plenty of rings punctuated his fingers as he clutched the mic.
To be immortalised in a portrait by David Hockney, Harry posed in an orange striped Molly Goddard button-up. The same designer he wore on the cover of his Harry's House album.
