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Radclyffe Hall - Reaching deep into the archives we find an original pioneer of androgynous dress. The author inherited a sum of money in her early twenties which is said to have allowed her to live independently and discard the feminine clothes chosen by her mother.

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Radclyffe Hall - Hall embraced her unique sartorial freedom and began visually expressing herself, particularly as a partner to the more feminine Una Troubridge, simultaneously championing one of the first modern examples of public lesbianism.

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Marlene Dietrich - The actress, once the highest-paid in Hollywood, genuinely loved wearing trouser suits, and said she felt more "alluring" in traditionally masculine clothes.
When she attended a 1932 film premiere wearing a tuxedo, Hollywood rippled with shock for her breach of gender norms, but mostly because she looked so compelling doing it.

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Coco Chanel - In the wake of WWI, women shed their corsets and shortened their skirts, but it was the impossibly chic Coco Chanel who put the ordinary women in trousers for the first time.

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Katharine Hepburn - The actress epitomized the independent American woman, and she was one of the first to popularize pants, commonly sporting a men's button-down tucked into high-waisted slacks, topped with a suit jacket. She once said, "Any time I hear a man say he prefers a woman in a skirt, I say, 'Try one.'"

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Bianca Jagger - Jagger was one of the first women to embrace Yves Saint-Laurent's revolutionary suit designs, proudly championing the novel silhouette for women and making it hard to argue that women shouldn't wear trouser suits. She even wore a suit jacket to her wedding!

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Twiggy - The British model and cultural icon was initially known for her thin build and her androgynous look, consisting of big eyes, long eyelashes, and short hair. Her adolescent physique perfectly fit the androgynous styles that began to emerge in the '60s, and her added *** appeal pushed the trend forward.

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Jean Seberg - Jean-Luc Godard's muse, and the Queen of French New Wave, charmed her way through cinema with her oversize sweaters, rolled-up pants, and signature pixie cut.

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Diane Keaton -

The revered actress has been a style icon since the '70s, and she’s a big fan of vintage men's clothing: well-cut shirts, high-waist baggy trousers, neckties, vests, and hats are her preferred style.

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Patti Smith - The "Godmother of Punk" famously enjoyed hanging out at the Chelsea Hotel with her great love, photographer Robert Mapplethorpe, and the two would reportedly swap clothes, which quickly ended up in Smith's signature look: collared shirts, loose neckties, blazers, pants, and boots.

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Robert Smith - While a plethora of rock stars pushed androgynous aesthetics, The Cure front man's smeared lipstick, eyeliner, pale skin and messy black hair, in addition to his trademark black-on-black attire, is a legacy that still echoes today.

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David Bowie - What Bowie did for fashion (while decked out in glittering onesies and platforms), and how he pushed the boundaries of gender and performance, is impossible to summarize in a few words. His impact on androgyny inspired an entire generation, and will continue long past his death.

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Boy George - The most famously flamboyant face of the New Romantics movement, Culture Club's Boy George crossed out gender lines with neon streaks of makeup, drowning convention with his wild hairdos and going boldly where few other stars had gone before.

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Prince - "I'm not a woman. I'm not a man. I am something that you'll never understand," Prince sings in 'I Would Die 4 U.' He explored this sentiment in four-inch platforms, bikini bottoms, curls, guyliner, jewelry, and lace, not only deconstructing conventional masculinity, but also pushing queerness and androgyny into mainstream pop culture.

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Pink - Pink's daughter once told her that her friends said she (the daughter) looked like a boy, and the singer responded by making a PowerPoint presentation of famous androgynous rock stars, from Prince to Annie Lennox, demonstrating the incredible, world-renowned beauty of androgyny. Pink said she's been criticized in the same way, but emphasized that it's the world that needs to change, not them.

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Rei Kawakubo - Japanese designer Rei Kawakubo founded her entire women's wear fashion line, Comme des Garçons, in the 1970s with the very literal motive to dress "like the boys."

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Grace Jones - The nearly six-foot-tall pop star, model, and Bond girl seamlessly and powerfully flipped back and forth from feminine seductress to executive masculinity, and she's credited with creating some of the most powerfully subversive imagery of our times.

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Jared Leto - The actor/singer has been in the spotlight ever since he was a teenager, and his style has reasonably morphed along with him, growing more and more daring, adding sequins here, some fur there. Now, with a sure footing, Leto has claimed that there is no singular definition of masculinity, and that it's "completely subjective."

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Cara Delevingne - The British model sports a style that varies greatly according to her mood and the occasion, combining her ability to balance on high heels with a love of laid-back hoodies and jeans. She even wore a tailcoat and top hat to Princess Eugenie’s wedding at Windsor Castle!

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Kurt Cobain - Cobain's nonchalance in wearing flower-print dresses, fuzzy blouses, and eyeliner only strengthened the powerful grunge movement's rejection of machismo and effeminacy, and spurred androgyny on as a fashion motif throughout the '90s.

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Kristen Stewart - On a daily basis, the actress prefers comfortable and relaxed clothes, with leather jackets, suits, t-shirts, and beanies as seemingly immovable staples. On the red carpet, she rocks chic and unique suits like this one.

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Young Thug - One of the more modern manifestations of androgynous fashion, the rapper once explained that he doesn't really believe in gender, which makes it easy for him to dress however he pleases. On the cover of his 2016 album 'Jeffery,' for example, he chose to wear a dress by Alessandro Trincone. "You could be a gangster with a dress, you could be a gangster with baggy pants," he said.

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Annie Lennox - The Eurythmics singer had a playful relationship with gender performativity, and its peak was probably at the 1984 Grammys when she showed up in drag (dressed as Elvis, no less). She explained,"It's a powerful thing when a woman wears something less feminine. It's saying: you must look at me slightly differently, I'm not just going to be a s***** object for you."

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Ellen DeGeneres - The TV host has been known for her "tomboy" style since the '90s, and despite criticism, she continues to wear what she loves: suits, tailored pants, and sneakers.

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Chloë Sevigny - The actor was an adorably androgynous trend-setter of the '90s, sporting a shaved head, boyish style, and an unapologetic rejection of femininity.

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Tilda Swinton - The actress has a highly fashionable and gender-neutral style, where suits are an essential and makeup is a rarity. Swinton also projects a timeless look with her tailored wardrobe of loose trousers, silk blouses, and impeccable knitwear.

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Agyness Deyn - The British style chameleon, instantly recognizable thanks to her punk-pixie cut, seemed to naturally gravitate toward more "manly" styles. In 2014, she launched fashion line Title A for Net-A-Porter, featuring dressy separates that perfectly balance the coquettish and the boyish.

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Janelle Monáe - The singer has always straddled the line between feminine and masculine, but she views her androgynous style as a political and social statement against s****m, as a stand against oppression and against other people's imposing belief systems.

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Andreja Pejic - Before coming out as a trans woman in late 2013, Pejić was known as the first completely androgynous supermodel, revolutionizing the fashion industry by appearing on both men's and women's runways. Today, she is one of the most recognizable transgender models in the world.

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Eliot Page - Eliot Page's Hollywood uniform is a suit and tie, but when he's off-duty he loves button ups, bomber jackets, and sneakers. He looks so comfortable!

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Rain Dove - The American model, actor, and activist has become the quintessential androgynous figure in fashion. Dove, who prefers non-gendered pronouns, is best known for posing as male and female models in photo shoots, productions, and runway shows.

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Jaden Smith - Will Smith’s son is doing a lot for younger men’s androgynous wear, combining traditionally masculine clothes with more feminine skirts, dresses, and accessories. He was also the first male to ever be cast in a Louis Vuitton women’s campaign.

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Ruby Rose -

The gender-fluid actress loves wearing gender-neutral clothes, favoring oversize suits, t-shirts, hoodies, and sneakers. She even launched a gender-neutral clothing line, Scallywags, with her former fiancée Phoebe Dahl.

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A$AP Rocky - The babushka scarf made waves in the fashion world, but the rapper has been making steady changes to his wardrobe, including colorful knit sweaters, mesh tops, flower-print jeans, handbags, and other traditionally feminine pieces.

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Lena Waithe - The actress/writer known for her work on shows like 'Master of None' and 'The Chi,' is similarly known for embracing the opposite of a conventionally feminine silhouette and getting playful with layers, prints, hats, and hairstyles.

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Harry Styles -

The singer cemented himself as a fashion icon in 2019, from his frilled Gucci shirt and Vermeer-esque pearl earring at the Met Gala to his unapologetic openness about his love for "women's" clothing. 

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Kid Cud -

Kid Cudi's campaign to normalize dresses in menswear has taken another step forward! The rapper appeared wearing a custom wedding dress designed by Eli Russell Linnetz to the CFDA Fashion Awards. It's an event that encourages guests to push the boundaries of fashion, and Kid Cudi clearly understood the assignment. He paired the white lace dress with a white tuxedo jacket, a veil, white sneakers, and grungey black eyeliner. The look seemed to be a tribute to Kurt Cobain, as Cudi Tweeted a picture of the late artist wearing a frilly white dress. 

This isn't the first time Cudi has paid homage to Cobain by wearing a dress. He performed on 'Saturday Night Live' in June 2022 wearing a floral gown with an identical pattern to one worn by Cobain in the past. During his appearance he made a statement about his androgynous style: “For me, it represents personal empowerment despite any social norm." He went on to say, "It vehemently represents confidence. It’s Cudi knocking on your television screen saying, ‘Hey! Be yourself.’” 

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Ezra Miller -

The up-and-coming Hollywood star has proved himself as something of a fashion icon, rocking incredible red carpet looks, from a floor-length puffer jacket gown to this shimmery look with glitter, silver-streaked hair, and a fluffy white coat.

See also: The many suits of androgyny icon Evan Rachel Wood

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