A guide to Harry Styles’ always evolving personal style
Silky PJs, Gucci suits, the One Direction era floppy hair – the musician is an evolving sartorial sign of the times
image Anthony Pham
words Louis Staples
Harry Styles has come a long way since he first stepped on to The X Factor stage in 2010. Today, he’s the man the world’s most famous designers would fall over themselves to dress. One of his on-stage costumes or photoshoots has the power to spark days of discourse on social media. And this week, he somehow managed to make patterned silk PJs look like the coolest thing ever. (On CBeebies, of all places).
But this didn’t happen overnight. From judge’s houses to hippy communes on the beach and Harryween, behold: the style evolution of Harry Styles, music’s most fashionable man.
With big floppy hair and a bubbly personality, Styles wowed the judges in his X Factor audition. And we all know what happened next. In the 2013 One Direction movie, This Is Us, the rest of the band said that Styles – who we first saw in a cardigan, an All Saints tee, and a skinny scarf – was the inspiration for the group’s early aesthetic. Thankfully, he soon waved goodbye to the Topman plimsolls (shudders) and Jack Wills tracksuits for an enviable selection of Saint Laurent, Burberry and, most notably, Gucci.
Breaking the mould
It was in 2013, when Styles was 19, that his approach to fashion moved in a different direction (pun intended) to his bandmates. Tattoos began to cover his body and skinny jeans and patterned Burberry shirts became wardrobe staples. His bandmates continued to sport boyish trainers and hoodies, but Styles walked his own style path. At the end of that year, he collected a British Fashion Award for his personal style.
A new direction
When One Direction took to the road in 2014 for the Where We Are tour, Styles’s status as the most directional dresser of the group was confirmed. He was rarely seen without a piece of Hedi Slimane’s Saint Laurent. Tuxedo jackets, Wyatt boots and silk scarves (much fancier ones than his X Factor audition) became regular features of his wardrobe, both on and off stage.
Going it alone
Styles’s first time on the road as a solo artist was when his approach to style and aesthetics became noticeably bolder. Brandishing his guitar and LGBTQ+ Pride flags on stage, he donned an array of custom Gucci suits, with the occasional Saint Laurent too. These weren’t run-of-the-mill suits, think: florals, leopard print, geometric patterns and sparkly fabrics. There was a clear 1980s influence here, with big hair and pussybow blouses. (And in Glasgow, he even wore a custom black kilt). Here, we start to see Styles referencing music icons from decades gone by, from a young Mick Jagger to David Bowie. (Though Jagger disagrees with these comparisons, claiming he’s much more androgynous).
As time has gone on too, he leaned into the happy hippy commune feel of the 60s and 70s, denoted in his high-octane ‘Watermelon Sugar’ video and off-duty flares and billowing candy-coloured shirts. Breathe it in.
The 1970s moustache
Styles clearly has an affinity for 1970s looks, so it seemed inevitable that he would grow a moustache at some point. We first saw this in 2020, when he visited chef Massimo Bottura while on holiday in Italy. He showed off his moustache while sporting a pair of baggy jeans, a green and white T-shirt and a pair of tinted Aviator sunglasses.
Styles is known for referencing adrogynous music stars, but here, there’s a hint of Robbie Williams – a British icon he grew up with – in the laddish flamboyance on display. (Suddenly, we’re craving balsamic vinegar?)
The Vogue cover
It was the cover that launched a million discourse-heavy tweets. It sent right-wing grifters into a full-blown moral panic and even Billy Porter took umbrage with it. But when Styles wore a dress on the cover of American Vogue, photographed by Tyler Mitchell and styled by Camilla Nickerson, it was clear that he plays by his own rules. Perhaps in years to come images like this won’t be unusual, but it’s hard to argue the Vogue cover won’t be one of his most important style moments.
When Styles joined forces with stylist Harry Lambert, his outfits on stage, in photoshoots and on red carpets became exaggerated, costumic and camp. From suggestively eating a banana wearing theatrical ruffles by androgynous, high-drama menswear brand Palomo Spain in Variety, to performing at the Grammys in a feather boa, here we can see the influence of a young Elton John on tour. His Met Gala 2019 look too was camp done Harry's way, in a sheer, black blouse by Gucci’s Alessandro Michele. Continuing this with his collaboration with Lambert, their partnership is defined by fearlessness, as well as playful provocation. These are outfits they want everyone to be talking about.
Dazzling for Dazed
2021 saw Styles branch out even further by launching Pleasing, his own beauty brand. To mark the launch, he graced the cover of Dazed. The former face of Gucci channelled his famously unfiltered fashion sense with lilac flairs and a cut-out tank top – which he paired with Comme des Garçons kitten heels. Other garments in the shoot included psychedelic Prada jumpsuits, a Swarovski choker and custom Gucci, plus archive pieces by Jean Paul Gaultier and John Galliano. Significantly too, he was styled by Dazed editor-in-chief, and Off-White art and image director Ib Kamara. If Styles’ status as music’s male fashion leader and key collaborator was ever in doubt, here it was underlined.
This year, Styles returned with a new album – and another new look. Ditching his staple frilly sleeves and metallics, he sported a more laidback ensemble for the new release, wearing head-to-toe Molly Goddard. The designer shared the image on her Instagram, writing that she had customised pieces from her spring/summer 2022 unisex and menswear collection for Styles. The outfit is somewhat of a departure for Styles, but it stays true to his playful approach when it comes to breaking down “barriers” in gendered dressing. Soft power for an album of loved up bangers and ballads.
Love on tour
For his mammoth 2021-2023 stadium tour, ‘Love On Tour’, Styles shines bright in all out ‘70s glitter and glam. Think sequin jumpsuits, feather boas and lots of purples, pinks and blues. This maximalist, stadium-ready style is Styles at his very best. But as the poster boy for Alessandro Michele’s Gucci era, his aesthetic might change as the brand welcomes its new creative director. Who will be the next designer to strike the jackpot by becoming a Styles fav? We’ll have to wait and see.