He’s one of the biggest stars in the world, and yet, ahead of the Love On Tour party rolling into town, Hannah Collins’ deep dive into Harry Styles’ career so far reveals an artist who splits opinion almost as much as he divides it, and as effortlessly as he breaks sales records and gender norms.

It’s hard to imagine a time that Harry Styles – one of Spotify’s most-streamed artists ever, the first man to grace the cover of Vogue, and founding member of one of the biggest boybands of all time – struggled to make it to the top. But he did, and very publicly. 

Thirteen years ago, a 16-year-old Styles, urged by a proud mother and his Battle Of The Band-winning mates back home in Cheshire, auditioned for The X-Factor. Despite obvious nerves – butchering Train’s Hey, Soul Sister – there was an ease with which he bantered with trouser-hoister Simon Cowell, a goofiness to his smile, and humbleness in the way he accepted that his mum’s view of his singing talents was biased: he was there to get a professional opinion.

Easy, goofy, humble. These are words that often come up in the same breath as Harry Styles, the 2010s teen heartthrob turned 2020s glam rock icon. A revolutionary in men’s fashion. The next Bowie. The man who maybe spat on everyone’s favourite Hollywood Chris. How true any of these things are makes Styles a more complex idol than he appears; a career that’s as divided as it is celebrated.

Even Styles’ time on The X-Factor was complicated: splitting the judging panel at his audition, being knocked out in the next round, and then being forced into a boyband to survive on the show. After barely two weeks of getting to know one another, the group performed weekly on live TV, and after all that, finished third in their season.

It’s rare, if not unheard of, to be privy to the very moment a band that became as absurdly famous as One Direction (1D) came into being. Seeing the gears so plainly turn under the hood of the machine should have made us impassably cynical about them. But perhaps it was this transparency that was the key to their early success. After all, we got to watch them bond, learn how to function as a group and navigate the music industry, the press and the public eye from scratch in near-real time. There was no pretence, no attempt to manufacture authenticity. It was all refreshingly honest – raw, even. However, as is so often the trajectory of the teen idol, with age came the desire for maturity and freedom. 

In 2016, Styles wanted to go solo again, having been subject to strict “cleanliness” clauses with 1D. Conversely, intimately invasive media and fan scrutiny accompanied this. “Suddenly, the screaming stopped,” Styles told Better Homes & Gardens. “In lockdown, I started processing a lot of stuff that happened when I was in the band.” He explained that he felt pressured to “get people to like [me]”. The cathartic release from striking out alone was aided by therapy to prevent himself from “emotionally coasting”.

This was the first big divide for Styles, one between Harry the One Directioner and Harry the One Man Band. In spite of the obvious launchpad a preexisting fanbase gives you, going solo must also feel like jumping out of a plane and scrambling for the parachute cord. Having described starting his solo career as liberating to the point of tears, Styles’ body of work and branding has, deliberately or not, personified this idea ever since. His music increasingly harks back to 60s and 70s rock and folk (Joni Mitchell, The Beatles, Pink Floyd, Van Morrison, Fleetwood Mac), eras famous for their seismic cultural shifts towards societal liberation. 

These are dated references you might think put a wall between Styles and his legions of young fans. But on the contrary, these are generations who communicate pejoratively via reference points, and for whom dad rock jams are a mere Shazam away. Sure enough, Styles’ debut single in 2017, Sign Of The Times, went quadruple platinum in Australia and triple platinum in the US; As It Was, the lead single from 2022’s Harry’s House, meanwhile, was the biggest song of the year according to Billboard.

You might also think this would make Styles far too mainstream for the ‘real’ music press. Wrong again. Rolling Stone inducted his second solo album Fine Line into its 500 Greatest Albums Of All Time list in 2020. Commentators were also giving Styles props for having legit indie sensibilities very early on: “Meet Me In The Hallway would be praised even more widely if it were by Bon Iver or Fleet Foxes,” the Observer’s Jude Rogers wrote in 2017.

Six years on, Styles reached a comfortable (and profitable) intersection between pop and rock star that continues to satisfy the masses and the critics; authentic and accessible. But not everyone’s ready to hail him as the Second Coming in British music.

Responding to David Bowie comparisons following Styles’ performance at this year’s Grammys, longtime Bowie collaborator Tony Visconti scoffed he wasn’t “worthy of shining [Bowie’s] shoes”. More than his music and performance skills, nowhere is the Thin White Duke more prominent than Styles’ wardrobe, from patchwork jumpsuits to frilled shirts and flared trouser suits. This affinity for the flouncier side of fashion, plus a refusal to pin his sexuality down into a neat little box, has also earned Styles plenty of critics, thus marking another divide in his career.

Conservative pundits saw the singer’s choice to wear a blue Gucci dress on the cover of Vogue in 2020 as an attack on traditional masculinity. “There is no society that can survive without strong men,” controversial political commenter Candace Owens tweeted. “The East knows this. In the West, the steady feminisation of our men at the same time that Marxism is being taught to our children is not a coincidence. It’s an outright attack. Bring back manly men.” Senator Ted Cruz even drew a bizarre line between the image and a painting of Bill Clinton in a dress apparently owned by Jeffrey Epstein. 

Not all progressives were thrilled with the dress either. Queer activist and actor Billy Porter, also known for playing with gender norms in his fashion choices, applauded Styles for normalising breaking down gender boundaries while noting the privilege enabling him to do so. “I had to fight my entire life to get to the place where I could wear a dress to the Oscars … All he has to do is be white and straight.” Porter later clarified that his issue wasn’t with Styles himself but the wider problem of appropriation. Others were quick to point out that men in women’s clothing are hardly new or shocking; indeed, Styles’ own musical idols were known for doing the same thing, which is likely where his inspiration came from in the first place. 

Many of these influences, notably Bowie, were sexually fluid, compacting the perception that only men who are sexually interested in other men would want to wear women’s clothes. As a result, Styles has also been plagued by accusations of queerbaiting. Once a niche term used in scholarly circles to discuss implied but not explicit LGBTQ representation being leveraged for commercial gain or clout, lately, it’s become popular parlance as lazy shorthand for anything that ‘looks kinda gay but isn’t’; an oversimplification with messy consequences. 

The key distinction is intent. Styles might ‘look kinda gay but isn’t’, but short of him French-kissing another man on-stage ala Madonna, Britney and Xtina, it’s hard to find any real evidence of actual queerbaiting. Rather, the demand that his fashion choices and insistence on keeping his sexuality private should be quantifiably queer plays right into the conservative narrative that gender and sexuality cannot be fluid. The amount of slash fan fiction out there concerning Harry and his former bandmates also can’t be ignored in all this: enough people projecting a sexual identity onto someone can make us look for ‘clues’ where there are none. 

As for Styles’ opinion on all this? He just wears whatever “looks cool”.

Further division can be found in the latest chapter of Harry Styles’ career: Harry In Hollywood. Outside of celeb cameos, Styles got his big acting break in 2017’s Dunkirk, where, to director Christopher Nolan, he was merely one of “thousands” of young men who auditioned for the role of stranded soldier ‘Alex’, eventually cast because the director thought he had a face that fit in with the era. “It’s not a showboating role”, he told the Daily Mail, adding, “Harry shied away from being a ‘star’ in it. He’s a humble guy who didn’t want attention.” Interestingly, Rolling Stone’s EJ Dickson made a similar point about The Dress. “The goal of the shoot wasn’t any different than that featuring a female model in a similar garment. […] What really incensed conservative commenters […] was precisely how mundane the image was.”

Unfortunately, while his ‘mundanity’ serves him well in war epics and fashion editorials, others have noted Styles has struggled to extend his acting range in more recent projects, like Don’t Worry Darling and My Policeman. Once again, the spectre of Bowie creeps back up, a rock star who successfully translated his natural charisma to the big screen.

Lack of confidence and inexperience – to go back his X-Factor origin – became painfully obvious during the disastrous press tour for Don’t Worry Darling, in which Styles’ leading man performance was decried as “leaden”. Opening up about his ‘method’, the singer revealed that he opts for the ‘head empty’ technique: “What I like about acting is I feel like I have no idea what I’m doing”. Oh dear. Then there was this gem on the nature of cinema: “You know my favourite thing about the movie? It feels like a movie, like a real go-to-the-theatre-film-movie.” Cut to co-star Chris Pine (who definitely wasn’t spat on) trying to hold his sanity together.

Have any of these divisions done irrevocable damage to the Harry Styles brand? Financially it doesn’t seem so if the neverending Love On Tour’s profits are anything to go by, raking in over £300 million worldwide since 2021. But even his stumbles are styled out by his forever-boyish goofiness. That goes all the way back to him charming Simon Cowell on TV at 16, being pantsed on-stage by his 1D bandmates, and his dress-up-doll attitude towards fashion. 

His comments on acting might portray an airhead, but Styles is deceptively sharp, carrying an innate understanding and respect for his largely young female audience while others sneer at them. “They’re our future,” he told Rolling Stone. “Teenage girl fans – they don’t lie. If they like you, they’re there.” He’s also thoroughly tuned into the rest of his fanbase: an ally, at the very least, to those who numerous surveys say are the ‘queerest’ generation on record, as well as one of the most musically pluralistic when it comes to genres and eras.

New and old, queer and not queer, Hollywood star and struggling actor, these are the contradictory elements that split Harry Styles’ career so far. But for those who study the past as much as they look to the future, this easy-going controversy-starter might not be all that new, but he’s always been the real deal, dresses and all.

Harry Styles: Love On Tour, Principality Stadium, Cardiff, Tue 20 + Wed 21 June.

Tickets: £46.25-£140.25. Info: here

words HANNAH COLLINS