It’s official: the gender divide has never been thinner. With unisex fashion lines, trans celebrities and androgynous beauty all making waves like never before, we take a look at 10 key moments that helped make this happen.

While androgyny has long been a part of the fashion landscape, from cross-dressing rock stars to tomboy-ish models, a new breed of designers refusing to conform to traditional binary notions of gender are challenging (or in some cases, completely shattering) our preconceptions of what men and women should wear. With Bruce Jenner blowing trans issues wide open on the international stage and a new wave of thought challenging outdated assumptions of binary gender we thought it high time to reflect on the fashion world’s many iconic androgynous moments.

Whether it’s appropriating garments designed for the opposite sex or crafting an all-encompassing gender-neutral aesthetic, here’s 10 iconic moments when fashion refused to play by the gender rules.

Katherine Hepburn

Modern gender-bending has it’s humble beginnings with a few very daring women in the 1930s – most famously Hollywood starlet Katherine Hepburn, who pioneered wearing pants. Causing quite the furore, Ms Hepburn regularly donned a mens button-down shirt tucked into high-waisted slacks with suit jacket, while fellow cross-dresser Ms Dietrich would also opt for a full tuxedo suit complete with top hat on occasions. While this might not seem like much today, this was once considered dressing in drag, so hats off to these women (among others) who held down their own and helped shape the concept of the modern American woman.

Grace Jones

Coming in at a staggering 5’10½”, Grace Jones’ height was feeble in comparison to her ferocious, diva persona, razor sharp jawline and aggro-feminine style. A fashion model gone rogue, Grace’s gender-thwarted appearance in the ’80s made her something of an unhinged deity in the eyes of the era’s most eccentric personalities and subcultures. Now, having solidified a position in the echelon of fashion’s most grandiose of icons, Grace Jones remains influential to a number of contemporary artists – as seen via pop acts Lady GaGa and Rihanna, who’ve admittedly cited Jones as inspiration.

The New Romantics

New Romanticism started as a small scene in early ’80s UK nightlife, and was quickly adopted by leading pop musicians of the time, with singer Boy George of Culture Club the most prominent figurehead of the trend. With the key word being “flamboyant,” the New Romantics – as the trend’s followers came to be known – wore androgynous clothing alongside brightly sculpted make up looks and wild hair. Blurring gender lines where men looked more feminine and women looked more masculine, it resulted in an overall neutral effect, especially for the excessive 1980s.

Robert Smith

While there are myriad rock stars who pushed androgynous aesthetics – from KISS’s outrageous circus of hair and leather to Alice Cooper’s out and out gender bending, it’s cult Goth figurehead Robert Smith whose legacy in androgynous dressing that still echoes today. Smith’s trademark image of smeared lipstick, eyeliner, pale skin, messy black hair and all-black getup would define the Goth aesthetic and matched the Cure’s gloomy, sombre music perfectly, and while the Cure frontman hated his band’s connotations with the Goth movement, designers are still drawing on the Goth aesthetic to this day.

Kurt Cobain

Grunge style will be forever associated with disheveled flannels, battered Chucks and ripped denim, but the movement paid host to a strong androgynous streak too, with Kurt Cobain’s nonchalant cross-dressing epitomizing the movement’s rejection of machismo and effeminacy. While the Nirvana frontman never cared to elaborate, stating “if I said we do it to be subversive then that would be a load of shit, because men in bands wearing dresses isn’t controversial anymore,” his donning of dresses, blouses and eyeliner would frame androgyny as an ongoing motif in 90s fashion. Cobain’s influence can be seen everywhere from Marc Jacobs to Saint Laurent, with Hedi Slimane’s second collection for the Paris house featuring dresses that directly paid homage to those from Cobain’s wardrobe.

Calvin Klein’s 90s Campaigns

While androgyny wasn’t anything new by the ’90s, Calvin Klein’s influence brought it to the masses. Coinciding with the grunge movement, the brand popularised genderless clothing in the form of boot cut jeans, basic T-shirts and unisex fragrances. Ad campaigns that featured effeminate men, desexed women, and gay couples kissing, blurred gender lines and brought about a modern, mainstream approach to the matter.

Kanye has always pushed hip hop style into new places, famously donning a Givenchy leather kilt for the Watch the Throne tour, but it’s his appropriation of a Céline blouse at 2011’s Coachella festival that will go down as one of Yeezy’s greatest fashion moments. Brazenly wearing the silk number bare chested and accompanied by numerous gold chains, it was a flamboyant turning point that showed just how far hip hop style would go in future years – from the baggy, blinged-out nightmare of the “00s to the present day where rappers are draped in skinny jeans and slim-fitting silhouettes.

JW Anderson

While JW Anderson has openly stated “I never set out to work on the concept of androgyny…I find [it] quite a dated concept,” the London designer and Loewe creative director has taken the high fashion world by storm with his unisex aesthetic that deftly avoids of gender-specific motifs. Anderson’s aesthetic remains largely the same across both men’s and women’s lines, giving a unisex feel to the line that sees menswear pieces cut and cropped to reveal shoulders and midriff and softer fabrics and palettes.

Selfridges Announcing Genderless Collection

It may be renowned as a luxury department store in the truest sense of the word, but that hasn’t stopped Selfridges from pushing boundaries with thier “Agender” pop-up concept. Delivering a truly genderless experience where customers shop from one unisex collection, Selfridges’ buyers noticed that men and women were increasingly shopping from each other’s departments and reacted accordingly. The concept pushed androgyny into 21st century – rather than simple cross-dressing, the pop-up offered contemporary avant-garde designers like COMME des GARÇONS, Nasir Mazhar, UEG and Haider Ackermann and styled them in a unisex manner that avoided any motifs bombers with wide-legged, skirt-like shorts and graphic tees were slimmed down and cropped.

Andreja Pejic

Along with Riccardo Tisci muse Lea T, Australian model Andreja Pejic has made waves in the high fashion world thanks to her sharp androgynous features, challenging traditional conceptions of beauty and bringing trans models into the spotlight. Having previously walked both men’s and women’s shows for Jean Paul Gaultier in 2011, Pejic came out as transexual and is the first openly transgender model to star in Vogue in May 2015 issue. For professional models, a major beauty contract not only provides huge exposure but guarantees the sort of long-term financial stability that the career so often lacks, so Pejic set a new milestone for transgender models when she was named as the new face of Make Up For Ever.