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8 most fashionable gender benders of all time

By Jackie Mallon

Apr 12, 2019


In 1994 Jean Paul Gaultier, the Parisian designer known for wearing a kilt with a peroxide short back and sides, created JPG by Gaultier, the first collection that promoted the idea of fluidity of the sexes outside of the space-age 60s when genderless clothing meant his and hers shaved heads and matching synthetic jumpsuits. A decade later, Gaultier sponsored an exhibit in the Costume Institute of New York's Metropolitan Museum of Art entitled "Braveheart: Men in Skirts.”

Gender non-conformity might seem like the current fashion industry buzzword. But before merchandisers offered us murses, guyliner, man buns, and boyfriend blazers; before Billy Porter posed on the red carpet; before gender was defined on a spectrum, the word “queer” was reclaimed and masculinity turned “toxic,” disruptive elements were at play––and oh, what play! Whether to redefine themselves, or confound society’s perceptions, or simply to be outrageous on the dancefloor, people have been swapping their panties with their pants for kicks and giggles throughout history.

So to coincide with the explosion in the market of unisex clothing and the first major exhibit to examine the relationship between fashion and gender entitled “Gender Bending Fashion” at the Museum of Fine Arts in Boston, we have gathered the 8 most influential gender bending pioneers. It’s an equal sprinkling of traditionally male and female presenting, with examples ranging from subtle code switching to utter flamboyance, at least by the standards of the day.

Joan of Arc

The victorious female warrior dressed in male armor, becoming a martyr for her beliefs, provides a timely symbol for contemporary feminists and social justice warriors who connect with her heroism and strength. Debates rage on the gender identity and sexuality of the persecuted Maid of Orléans who was executed by the English in 1431, burned at the stake. Legend has it that she believed presenting as male was in accordance with God’s wishes but also prevented her from being violated in the night by guards. Hailed and vilified in equal measure, as a witch, a saint, a heretic, this androgyne’s story shares parallels with the contemporary LGBTQ+ struggle, and has inspired designers like John Galliano and Alexander McQueen, and fashion photographers such as Tim Walker and Herb Ritts

Patti Smith

Patti Smith describes in her memoir Just Kids her search for identity and self-expression through poetry, sketching, photography and music, but it is on the cover of her 1975 album Horses, photographed by another fashion favorite Robert Mapplethorpe, that her self expression epitomizes gender fluid chic. Dressed in a white open-necked man’s shirt, sleeves rolled up, with a black tie unknotted, blazer slung over one shoulder, and black hip-clinging pants, she oozes effortless female empowerment while looking like a boy. Already the breadwinner in her relationship with Mapplethorpe, she found being the lead singer of a band in 70s male-dominated New York City punk era challenging and has recounted the difficulties of finding band members who weren’t threatened to perform behind a woman. Hedi Slimane has devoted his design career to attempting to emulate Smith’s rock star nonchalance on runways from Dior to Saint Laurent to Celine.

Katherine Hepburn

Katherine Hepburn’s strong-shouldered blazers and roomy pants complete with loafers lent her a hands-in-pockets swagger both onscreen and off when this was still an unorthodox look for women. In 1951 Claridges of London reportedly forbade her from wearing slacks in the lobby, so she entered by the staff door. The ease with which she styled menswear classics managed to be both sporty and provocative, paving the way for Diane Keaton’s Annie Hall and Mary Kate and Ashley Olson’s The Row. An independent spirit with a passion for tennis, golf, and cricket, she once declared, “If you obey all the rules, you miss all the fun.” But in 1935, when she chopped her hair to play a cross dressing con artist in the movie Sylvia Scarlett which ultimately flopped, she gained the reputation of being box office poison. How’s that for toxic masculinity?

Boy George

When Boy George emerged in the early 80s, with his meticulously applied graphic make-up, colored ribbons braided though his hair, and soulful voice, the world struggled to process what it was witnessing. But his Dietrich-defined eyebrow, colorful kimonos, pirate headwear and coy smile were intended to perplex. He has said, “I look at myself at 19 and think I would never do what I did then now! I was so brazen, so confident, so fearless in a way. And remember, the world was a very aggressive place then. People would punch you in the face [for looking different] — and that happened a lot to me.” Originally spotted by music entrepreneur Malcolm McLaren, then partner-in-punk of Vivienne Westwood, Boy George became a regular at London nightclub, Blitz, where milliner Stephen Jones and a young John Galliano also partied. “Being with other creative people like Boy George was a crucial experience for me,’ Galliano has said. Boy George’s fashion credentials were established early.

Marlene Dietrich

“I am at heart a gentleman,” said Dietrich, who became known for her bold silhouette of lean masculine suiting, top hat, and cloud of cigarette smoke. This gentleman’s heart was put on display in the 1930s movie Morocco when a tailcoated and bowtied Dietrich kisses a female member of the audience on the lips. Fast forward fifty years and Madonna is mimicking her style, is kissing Britney Spears on stage. Threatened with arrest in 1933 by French police if she arrived in Paris wearing her signature pants, forbidden for women, Dietrich wore them anyway. Openly bi-sexual, her affairs with women during the 40s and 50s represented the same bravery that she demonstrated when she escaped Nazi Germany, only returning to entertain US troops on the frontline. Her gender fluidity was captured for posterity by fashion photography’s greats, Irving Penn, Richard Avedon, Eve Arnold and Cecil Beaton, and has inspired design greats such as Giorgio Armani and Yves Saint Laurent.

“Glamour,” Dietrich once remarked, “is assurance. It is a kind of knowing that you are all right in every way, mentally and physically and in appearance, and that, whatever the occasion or the situation, you are equal to it.”

David Bowie

Nods to the styles of Marlene Dietrich and Katherine Hepburn can be spotted in David Bowie’s looks throughout the years, but it is as Ziggy Stardust when he prowled the stage––like a tiger on Vaseline––in a one-legged knit leotard by Kansai Yamamoto and women’s heels, or when he reclined on a chaise in a Mr Fish dress with Pre-Raphaelite locks for the cover of The Man Who Sold The World that he still dominates the conversation on gender non-conformism. Dressed in drag in the video for “Boys Keep Swinging,” he wiped his lipstick off on the back of his hand, a gesture mimicked by singer Lorde at the American Music Awards three decades later. A major influence on Boy George, Bowie remains a beacon for gender questioning youths who, only discovering him upon his death, identify a likeminded soul who valued otherness above labels, and who placed mutation, performance, transgression, and emotion at the heart of his personal style.

Candy Darling

Immortalized in the Velvet Underground’s “Candy Says” and Lou Reed’s “Walk on the Wild Side,” the actress was a central figure of downtown Manhattan’s always fascinating late 60s, early 70s nightclub scene, a staple of Warhol’s factory and one of his Superstars having starred in 1968’s Flesh and 1971’s Women in Revolt. But while Warhol remains foremost in fashion’s consciousness, due partly to a Whitney retrospective which has just ended, and the many references made by Raf Simons through his Calvin Klein collections, this iridescent peroxide goddess in the Uma Thurman mold remains in the shadows. But not for long as a biopic of her life is currently in the works.


Virginia Woolf’s 1928 novel about a nobleman’s century-spanning journey from Elizabethan era England to modern times during which he becomes a she was adapted for Hollywood in 1992, and the fashion world was thrown into a frenzy at the sight of Tilda Swinton as the title character. The movie was a masterful merging of Woolf’s pioneering material and mesmerizing casting––look out for Quentin Crisp as Queen Elizabeth I. Swinton has continued to defy traditional gender representation throughout her career landing herself on international best dressed lists, in a David Bowie music video, and in the role of muse to Dutch design duo, Viktor and Rolf.

Fashion editor Jackie Mallon is also an educator and author of Silk for the Feed Dogs, a novel set in the international fashion industry.

Photos Joan of Arc miniature between 1450 and1500, oil on parchment, Archives Nationales; Publicity still of Katharine Hepburn in the 1942 film ''Woman of the Year,’' David Bowie shooting his video for Rebel Rebel in AVRO's TopPop (Dutch television show) in 1974, Licentie afbeeldingen Beeld en Geluidwiki, Boy George performing at Ronnie Scott's in London 2001 by Jessica Hansson, Marlene Dietrich with top hat in Morocco (film) 1930, Josef von Sternberg, director, Paramount Pictures, all Wikimedia Commons, Screenshot of Orlando directed by Sally Potter