Five years ago, menswear was all classic suits, stiff denim and a beard that birds could nest in. Masculinity was ‘in’ as designers tapped blue collar professions for inspiration, to assuage the modern man’s guilt about his soft hands. But then, things changed. Edges began to blur. Silhouettes softened, women turned up on menswear runways and the two were suddenly tricky to differentiate. And slowly, ever so slowly, androgynous fashion went from industry buzzword to high street rails.

It’s an idea that’s recurred throughout fashion history, but in the last few seasons the look has diversified. Rick Owens sparked a ‘genderless’ fashion movement in 2015 with flowing, oversized silhouettes that hid the body inside them. The ensuing ‘health goth’ trend blew up so hard even Selfridges launched an Agender department.

But sexless fashion, with its neutral pieces that come without gender baggage, proved a precursor to something more radical. There’s been a shift in recent seasons from shapeless clothing to overt femininity; though the man skirt is a regular feature at menswear weeks, it’s now joined by pussy-bow blouses, cut-out tees, even high heels, courtesy of designer Andreas Kronthaler at what used to be Vivienne Westwood’s Gold Label.

And unlike earlier attempts to blur gender boundaries, which were arguably geared more towards garnering column inches than sales, this time it seems it might stick. When Louis Vuitton cast Jaden Smith as the face of its womenswear the ensuing headlines were overwhelmingly positive. Elsewhere, Alessandro Michele’s androgynous bohemian aesthetic has turned Gucci into fashion’s most desirable label. There’s a chance that, this time around, ‘dressing like a girl’ could infiltrate the mainstream.

Alessandro Michele’s androgynous aesthetic has turned Gucci into fashion’s most desirable label

We’ve been dressing to our gender since the 14th century, according to fashion historian Benjamin Wild. Before then, both sexes wore takes on the same clothes, styles dictated by the most practical way to cover up. But with the birth of fashion, garments began to reflect the bodies that lay beneath them. Mens- and womenswear split and ideas of what constituted masculine dress were cemented over centuries. What we wear became shorthand for social notions of what it meant to be a man.

Androgyny is taboo because it’s unexpected. “It challenges social and political conventions,” according to Wild. “[It doesn’t] become the clothing convention.” Which is why gender-blurring on runways has always felt shocking, and never managed the transition out of fashion week. “As humans, there’s a level of conformity that comes with dressing,” says Nik Thakkar, one half of London design duo Ada + Nik. “We have to adhere to what society expects – sometimes for your job, sometimes to avoid being murdered by a narrow-minded bigot.”

But why should our wardrobes stay gendered as some other divisions that have historically separated the sexes begin to dissolve? As women moved into the world of work and cast off domestic burdens they adopted traditionally masculine clothes – suits, trousers, a mode of power dressing – to grasp some of the patriarchy’s power. But femininity has been synonymous with powerlessness for so long that to adopt its markers means lowering your social status. The thinking goes, if you dress like a girl, you can expect society to treat you like a girl.

Jaden Smith was cast as the face of Louis Vuitton womenswear

Hence the confusion between androgyny and drag, a style entwined with a gay culture that society has long seen as equally feminising. Our clothes say things about us that veering from masculine markers challenges. It confuses an audience primed to put people in boxes according to their gender, their class, their standing in society. An androgynous look on Gucci’s runway exists within a context of challenging convention. Translate that to the street and it unsettles narrow minds.

It’s why androgyny’s icons have served up their gender-bending with a dose of virility. Prince may have favoured a jumpsuit and high heels, but he put accusations of femininity to bed along with scores of young women. And although David Bowie’s sexuality seemed as liquid as his personas, his androgyny was filtered through characters; Ziggy Stardust might be a cross-dressing bisexual alien, but as he told Rolling Stone, David Bowie was, “a closet heterosexual”.

Their looks were an extension of their confidence and the overall aura that made androgyny palatable, and attractive, to a broad spectrum of men. And rock ‘n’ roll, whose stars are expected to be showman and swordsman, has often been androgyny’s safe space. No surprise that gender-blurring’s most successful infiltration of the mainstream, the skinny jean, was ripped from stages.

“It all stemmed from the days of Hedi Slimane, where boys had to be resourceful and often resorted to women’s high street collections,” says stylist Alexis Knox. It’s a look that still offers a socially acceptable way to dabble with femininity.

But as any man who’s tried to squeeze into their girlfriend’s jeans can attest, the sexes are not shaped the same. Which poses a challenge for designers trying to steer genderless. “It can work for separates, lightweight material tops and even jackets,” says Thakkar, “but the male and female form are different shapes. If you want a form-fitting piece, it needs to be designed with a specific demographic in mind.”

High street giant Zara reinforced this earlier this year with their ‘Ungendered’ range, which essentially saw baggy jeans and shapeless tees rebranded in order to appear progressive.

High street giant Zara recently launched its unisex Ungendered range

A man in a pussy-bow blouse and a dress remains an aesthetic loaded with cultural and political implications despite society gradually broadening its views on gender politics. Designers may be introducing new alternatives to traditional menswear, but these alternatives usually stay in the metropolises, places where prevalent gay cultures and arts communities have inured their fellow commuters to convention-flouting clothes.

But so long as designers like Ada + Nik, Charles Jeffrey, Craig Green, and Alessandro Michele fight against expectations, the menswear industry will become more progressive, more feminine, and far more interesting.

Gradually, these softer silhouettes, these androgynous styles, will filter down. We’re still some distance from men in heels being de rigeur in your local. But you can wear skinny jeans and a sheer tee without a second glance.