With a penchant for skirts, sequins and pussy-bow blouses alongside tailored suits and skinny jeans, singer and actor Harry Styles has become the poster boy for gender-fluid fashion. Melissa Twigg explores this gradual shift in cultural norms and what it means for the rest of us

Last November, Harry Styles made fashion history by being the first solo man to grace the cover of American Vogue – and he did so while wearing a rather lovely frock. Dressed in a full-length gown designed by Gucci’s Alessandro Michele, paired with a tailored black jacket, Styles looked every inch the superstar he is for this dreamy shoot on the cliffs of West Sussex in England.

While the singer and actor is far from being the first man in the public eye to test gender norms, he is one of the biggest stars to do so. The decision by Vogue to photograph him in pieces we would have once seen on female stars was a bold one, and a sign that Anna Wintour was determined not to let American Vogue fall behind Edward Enninful’s British edition when it comes to testing boundaries. 

Shot by Tyler Mitchell – the man who photographed Beyoncé for her 2018 Vogue cover – Styles’ own distinctive, largely genderless, look was central to the aesthetic of the shoot.  “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,” Styles said in the accompanying interview with fellow Brit Hamish Bowles. 

Michele, the creative director of Gucci, believes we shouldn’t underestimate the influence of a star like Styles and his ability to shift the way an entire generation dresses. “He’s really in touch with his feminine side because it’s something natural,” he told Vogue. “And he’s a big inspiration to a younger generation – about how you can be in a totally free playground when you feel comfortable. I think that he’s a revolutionary.”

Styles has been regularly spotted in kilted skirts by Wales Bonner, chunky chain belts by JW Anderson and pussy-bow blouses by Gucci. For the shoot, Jonathan Anderson produced a trapeze coat, John Galliano at Maison Margiela made a khaki trench with a portrait neckline and Harris Reed – a Central Saint Martins fashion graduate who ended up making some looks for Styles’s 2020 tours – spent a week making a smoking jacket with high-waisted, wide-leg trousers worn with a ballet-slipper-pink tulle skirt.

Reed himself has been central to this new gender-fluid approach to men’s fashion. The 24-year-old British-American designer believes that fashion is entering a new period of exuberance and his own collections – as well as his own personal style – are a testament to this. His bold designs play on aesthetics reminiscent of both the David Bowie ’70s era – bell-bottom suiting silhouettes, ruffled blouses, and millinery – as well as the flounces and embellishments of the Romantic period, when men regularly out-frilled women. 

“Gender-fluid clothing has become a vessel to be taken in whatever way you see fit,” Reed said in an interview with GQ. “I might wear the same blouse I made for Harry, and I might wear it in a very feminine and sweet and innocent way. Harry’s on stage, chest fully out, sweating, rocking out. He really reclaims it for his own self.”

Since his Vogue cover, Styles has only become bolder. Easing away the first hint of January blues this New Year, he released the aptly-named, wonderfully cheerful Treat People With Kindness single on the first day of the year, starring none other than Phoebe Waller-Bridge. The all-singing, all-dancing duo were dressed identically in silver glitter jackets, white slacks, diamond-print jumpers and shirts with embellished silk cuffs. The entire aesthetic felt a world away from the music videos of a decade ago, when men wore sober suits and women were either half-naked or trussed up in platform heels and revealing dresses.

Then, at the most recent Grammys, Styles wore a Gucci jacket and slacks with a feather boa flung around his neck. Later on stage – dressed in head-to-toe leather – he kicked off the evening with a captivating performance of Watermelon Sugar. Still in Gucci, he wore a cropped jacket and flared trousers with leather boots from the brand, his signature rings and a sea-green faux feather boa. Styles proceeded to shed the boa during the chorus, revealing his tattooed chest under the jacket. 

While male pop stars in the ’70s and ’80s played with gender norms, since the ’90s, men’s fashion has largely operated within strict lines of masculinity – and that has permeated the culture as a whole, with male self expression limited to either tailored workwear or street style. Now, this new gender-fluid approach to dressing has given men new parameters to play with.

And while certain people in the public eye love to rail against icons like Harry Styles (note American right-wing commentator Candace Owens decrying the “feminisation of our men”) none of this should be particularly controversial, given the fashion industry has been moving in a gender-neutral direction for a while. 

Many of the Gucci pieces Styles has worn are drawn from a unisex, rather than a womenswear, collection while JW Anderson has been pushing genderless fashion since 2013. Equally, Lewis Hamilton was shot on the cover of GQ in a skirt in 2018, and in the US Kanye West has had a similar impact on men’s fashion both through his fashion brand Yeezy and his personal style.

But mostly we should celebrate this new era for the fact it has given everyone the opportunity to wear clothes that say something about who they are, and not just their gender – including women, who are becoming less hemmed in by cultural norms as we move away from highly masculine or feminine dressing. 

“I’ll go in shops sometimes, and I just find myself looking at the women’s clothes thinking they’re amazing,” says Styles. “It’s like anything – anytime you’re putting barriers up in your own life, you’re just limiting yourself. There’s so much joy to be had in playing with clothes. I’ve never really thought too much about what it means – it just becomes this extended part of creating something.”