George Sand (1804-1867)
Like her British counterparts, the Brontë sisters and George Eliot, this pioneering French writer (born Amantine Aurore Lucile Dupin) took a male pen name before it was acceptable for women to publish books. But, as you can see in the image above, she also wore men’s clothes, which she felt were more comfortable, and smoked cigars — a big no-no for ladies, especially of her class. Despite her aversion to dresses, Sand managed to win the hearts of such famous contemporaries as Prosper Mérimée and Frédéric Chopin.
Radclyffe Hall (1880-1943)
The woman behind then-controversial lesbian novel The Well of Loneliness always knew she loved women. And, like some of the characters in her books, she assumed a rather masculine style of dress that suited her short haircut and strong features.
Marlene Dietrich (1901-1992)
Although no one would mistake her for a man — and she looked equally comfortable in a sparkling evening gown or a suit — Dietrich’s signature style combined a little bit of Sand and a little bit of Hall with a whole lot of glamor. She smoked, she partied, she frequented gay bars, and she seduced men and women with enthusiasm.
The Cockettes (Late ’60s)
Founded and evangelized by Hibiscus, a fellow known for mixing colorful frocks, glitter makeup, with a flowing beard, San Francisco’s own gay, hippie performance troupe didn’t just perform in drag. The group actually lived an (acid-fueled) post-gender lifestyle. In the few years before they combusted, The Cockettes inspired everyone from John Waters to Britain’s glam rockers.
Patti Smith (1946-)
This year’s National Book Award recipient first rose to fame in 1975, with the release of her debut album Horses. Smith was always an oddball and gender non-conformist, and her style reflected that — for instance, she stole her famous choppy hairstyle from none other than Keith Richards and posed for the Horses album cover (photographed by Robert Mapplethorpe) in a suit with suspenders. According to a friend who knew both of them in the early ’70s, for a while there, Smith and Mapplethorpe looked almost exactly alike.
David Bowie (1947-)
With his slight build and high cheekbones, Bowie was born androgynous. In the early ’70s, he helped nature along by wearing what he called a “man’s dress” on the cover of The Man Who Sold the World, before mutating into full-on, makeup-loving, leotard-sporting bisexual alien Ziggy Stardust. These days, the musical shape shifter is looking less ambiguous, but we’ll always remember the early ’70s as his — ahem — golden years.
Grace Jones (1948-)
You may not guess Grace Jones’s gender just by looking at her — but we’d be surprised if she didn’t dazzle and intrigue you nonetheless. The bisexual star’s striking suits, elaborate makeup, and flat-top haircut launched her to fame as a truly unusual model, musician, and actress — with a major gay following.
Annie Lennox (1954-)
Lennox’s signature look, from her Eurythmics days, is pure androgyny: close cropped hair, a business suit and tie, and a face full of glamorous makeup. Her sensual growl on classics like “Sweet Dreams (Are Made of This)” didn’t hurt, either. In her solo career, Lennox has switched things up, donning elaborate period dress for her “Broken Glass” and “No More I Love You’s” videos. Still, the thick, arched eyebrows and chic, nearly buzzed haircut remain.
Tilda Swinton (1960-)
When it came time to cast a single actor in the role of Orlando, the hero who suddenly transforms into a heroine in Virginia Woolf’s novel of the same name, director Sally Potter made a brilliant choice. Who could play the part but Tilda Swinton, a brilliant and iconoclastic actress who cut her teeth working on the gender-fucked films of Derek Jarman? She’s the ultimate thespian transformer; although her default look is androgynous, Swinton makes both a beautiful lady and a dashing gent.
Boy George (1961-)
He may be a punchline these days, but back in the ’80s, Boy George was the poster boy for New Wave gender bending. His long, braided and dreaded locks, Cindy Lauper accessories, and airbrush-y makeup gave the baby-faced Karma Chameleon a striking rock-chick look.
Marilyn Manson (1969-)
Like the other members of his band, Marilyn Manson assumed a female movie star’s first name and a serial killer’s last name. But he’s the one who brought a goth spin on androgyny to the mid-’90s mainstream. It’s not that Manson ever looked quite like a woman. In his torn corsets, plastic jumpsuits, and horror makeup, he simply transcended gender altogether.
Antony Hegarty (1971-)
The Antony and the Johnsons mastermind creates gorgeous art that thrives on gender ambiguity. Although he uses the male pronoun, he also identifies as transgender. And yet, even that term doesn’t encompass the range of Hegarty’s identity. In fact, we constantly feel like he’s clearing the way for new, non-binary gender expressions in the future.