The History of Gender Bending Fashion

The deep connection between queer history and the fashion we see today.

What is Gender Bending?

Gender Bending. Pushing against heteronormative ideals about gender and its relationship to the clothes we wear. Bottom line: gender is a construct, not a fact.

 This simple truth has always been at the heart of queer style. It was the queer community who first challenged society’s ideals about gender loudest and proudest, best encapsulated in the fashion he, she, or they wore, unapologetically so, sometimes even in public spaces where both civilians and the police were forced to reckon with the idea of nonconformity.

Listen, fashion has always been used as a conduit for self-expression.  Punks wore spikes and chains as symbols of rebellion.  Royalty wore tiaras to signify wealth and position, but it was the queer community who decided to challenge gender stereotypes through their choice of cloth.  And they did so to topple the prevailing sentiment that it’s the clothes that reflect one’s gender, rather than the other way around.

The revolutionary thought was really quite simple: My clothing doesn’t dictate my gender, I do.


It wasn’t easy, though, historically, to live this ethos as the legal apparatus was setup to criminalize gender bending/fluid style.

Throughout the 1940s to 1960s, “three-piece laws” meant trans people had to wear three articles of clothing that were associated with their birth-assigned gender to avoid getting arrested for cross-dressing.

Via: BBC

Everything changed with the Stonewall Uprising of 1969.  This event became THE marker for the gay liberation movement that was to follow and had great impact on queer fashion rights.  Until then cross dressing, bending gender norms, remained illegal.  Drag queens and kings were arrested frequently.  When the 200 patrons of Stonewall decided to fight back against the police, it was really the first time the queer community had publicly and in such large numbers resisted against ‘the man’.  This outward defiance led to an unprecedented societal acceptance of cross dressing, particularly, in public. Cross dressing arrests decreased subsequently (still legal in SF until 1974).

The 1980’s queer culture

Ryan Murphy, the renowned producer behind hits like Glee, American Horror Story, and Pose, said it best when he said: “Beauty and glamour and light and music. That’s how we as gay people and trans people have gotten through our pain”.

Think about the Harlem ballroom culture of the 1980s – glitz, glam, a sheer extravaganza for the senses, an opportunity for marginalized queer folk to congregate and celebrate through brazen, bold, and unapologetic style. These were elaborate pageants, complete with catwalk competitions, and vogue battles.

Via: The Rolling Stone

Runway categories like ‘Femme Queen’, ‘Butch Queen’ and ‘Sex Siren” meant that the disenfranchised had the chance to throw a big middle finger to commercial constructs of gender.

These categories often played with notions of not only gender but race and class, too. Queens walked executive looks (how well one could pass as a corporate worker), thug realness (hyper-masculine representation), and ethnic.

Through these categories, the queer community could explore themes of resistance and conformance, both breaking gender norms and acknowledging that, in order to fit into a society that condemned them, one would have to embody the archetype as well as possible.

Fashion became about escapism for the queer community, a fantasy of who they were in the deepest part of their souls. It allowed participants (predominantly black and brown folks) to construct their own worlds, spaces, and identities, and in a safe space.

Via: Vogue

Gender didn’t matter and modern constructs of it were pushed, prodded, and poked. The queer community, once again, proved itself ahead of the fashion curve, as real pop culture progressives. Think about the terms “Werk, shade, realness, slay, yas”. Queer origins!

Genderbending in the mainstream world

We have come a long, long way, and I have to say, the power of celebrity has played a huge role in exporting gender fluidity in fashion across the globe.

In the 90s, stars like Ru Paul, Grace Jones, Prince, and Boy George paved the way for new constructs of what it means, today, to be fluid (in dress).  Each also played with new understandings of the relationship between gender, sexuality, and fashion. Jones/Prince arguably straight, didn’t subscribe to gendered constructs of style, proving it’s not one’s sexuality that necessarily dictates how one dresses.  Why are we a society so obsessed with labels?

Via: Billboard

The 2000s brought us fashion design powerhouses like Marc Jacobs and icon Lady Gaga, both flirting with the idea of gender reconstruction.  Jacobs in his campaigns, his own dress sensibility, and his choice of models.  Gaga in her belief in gender fluidity and her appearance at the 2011 VMAs.  And because both of these stars have broad, commercial appeal, the masses, who ordinarily might not be exposed to alternative modes of being and of fashion, had a gateway to the other side.

Via: Billboard

Today, you can look at the most important single event in global fashion, the annual Met Gala, sponsored by Anna Wintour and Vogue, and its 2019 theme of Camp: Notes on Fashion, The Met’s first explicitly queer exhibition.

The exhibit thereafter as well as the night itself concerned itself with camp decadence, theatricality, and many of the tenets of the fashion indicative of queer culture.  At the heart of it all was an adherence to gender nonconformity and homosexuality as key foundations of camp.

Queer celebrities in attendance like Lena Waithe, Ezra Miller and Keiynan Lonsdale epitomized what the gender fluid movement is all about: clothing is not gendered.

And then take stars like Billy Porter and Harry Styles.  Billy’s 2019 Oscars tuxedo gown – man up top, woman on bottom – was a blatant refute of compartmentalizing one’s fashion, and one’s gender.  And then Styles, though not openly part of the queer community, proves that sexuality doesn’t necessarily have anything to do with gender bending.  Straight people can be fashion-fluid, too.  There are no rules, which is exactly what the movement is all about.

Via: Vogue 

Canadian designers to support

There are so many wonderfully talented designers in Canada who choose not to conform to gender stereotypes when designing. Not only is it woke and reflects where we are in society, it also makes good business sense.  Here are a few of my favourites right now:

Pedram Karimi

Iranian born, lives in Montreal. Makes more sense from a social stance to design fluidly.  It also makes sense from a business/economical perspective to have 1 inclusive, broad spectrum collection, in lieu of a menswear and womenswear line.

Sara Armstrong

Gender inclusive designer living and working in Vancouver.  Cisgender, straight woman (don’t have to be considered queer to operate in the fashion fluid space), and not everyone who dresses fluidly identifies themselves as part of the queer community (which is the point).  Her design philosophy has always been that clothes are inanimate objects void of gender amongst other things (like season and age).  For Sara, clothes are for people and bodies.  People bring gender to clothes.  The interpretation is up to the wearer.


Winnipeg-based designer/retailer, known for home goods. Their pride initiative includes these inspired slogan totes sold exclusively in-store.  100 percent of the proceeds from the sales of the bags will go to a local charity in each city supporting the LGBTQ+ community.  What’s great is that the totes sport a monochrome design instead of the rainbow as the queer designers behind the tote believe it’s about creating an item that symbolizes pride you can wear any day/year-round.  The black and white bag is also meant to reject the corporate embrace of pride

Other gender-neutral clothing designers to check out: Old Fashioned Standards and Andrew Coimbra.