13 Groundbreaking Gender Bending Celebs

Whether androgynous, trans, gender fluid, or anywhere in between-- gender bending is where it’s at. From men not shying away from a little guyliner to women taking a page out of the Katharine Hepburn pantsuit, gender bending is the newest wave of social activism. Rock stars like Mick Jagger, Justin Bieber, Russell Brand, Adam Lambert, Annie Lennox and Miley Cyrus really know how to bend the rules… They didn’t make the list, but these folks did. Enjoy! 

Former Olympic swimmer turned model, Casey Legler, is the first woman to land a male modeling contract. Even more remarkable, in an industry dominated by our worship of youth, she started her modeling career at age 35. It was an easy fit for her at 6’2”. Legler is currently repped by Ford Models and is also hot as what. 

TIME magazine cover model, Laverne Cox, is the first of two from Netflix's Orange is the New Black to make the list. Cox has become an outspoken advocate and role model for the trans movement, having openly discussed the bullying she endured as a child and the slow process of embracing androgyny. Becoming a trans-lebrity and a straight up bada** actress are her latest additions to her storyline.

You can’t have a list of gender benders without including pop culture’s favorite lady-gent, Ruby Rose, who rose to fame with her role on the Netflix series, Orange is the New Black. Now you can’t turn on the internet without running into an article about her, and for good reason. Ruby identifies as gender fluid and lets her gender flag swing both ways. Love it. 

Before there was Ruby Rose, there was Kate Moeninng, the original boyish girlish panty-dropper. Moeninng starred in Showtime’s The L-Word as Shane. I’m not the first to draw a comparison between the two, and with their similar aesthetics and equally high status on the “hot-meter,” it’s easy to see why. Despite remaining relatively private about the details of her personal life, her role on the L-Word brought futch to the forefront of American pop culture. 

Amanda Lepour is nicknamed “the most expensive body on earth,” and from looking at photos, I wouldn’t be suprised if she actually sh** diamonds. Lepour is a mainstay in the New York nightlife. In Milan, they call her La Silicona. In my world, we call her, “Yas, gurl!” Lepour’s aesthetic is less about being seen as a woman and more about being seen as a goddess. She's had more plastic surgery than a Kardashian party, and is all kinds of wonderful to behold. 

The modeling industry makes a number of appearances on this list, so it’s safe to say gender androgyny is totes fashion forward. Rain Dove can be seen strutting the runway both in men’s and women’s wear. If ever you wonder why, she summed it up perfectly in an interview with Buzzfeed: “The gender thing doesn’t exist; it’s a social construct you don’t have to fit into.” Preach. 

Speaking of the modeling industry, Andreja Pejic has been on hormone blockers since puberty. She landed a modeling contract in her teens while working the register at a McDonald’s in her native Bosnia, and within a couple of years rose to No. 18 on the Top 50 Male Models list on models.com. Three years later, she underwent gender reassignment surgery and her modeling career didn’t skip a beat. At 24 she’s one of the model industry's "it" girls. 

One of the pioneers of gender fluidity, David Bowie, will forever live as a gender bending legend for his disregard for traditional gender norms. One of Bowie’s greatest gifts was the voice he gave to these underrepresented and often misunderstood sexual and gender fluid communities. In an era when talking about being gay was taboo, Bowie broke boundaries by talking about being pansexual. RIG, David Bowie: Rest In Glitter. 

Talent runs in the family, gurl. The Wachowski’s are Hollywood big wigs who rose to fame with their work The Matrix, which they co-wrote and co-directed. Lana hinted at her trans identity starting in 2000, while Lilly stayed out of the limelight until being outed byin 2016. 

NY Times Bestselling author and all around bada**, Janet Mock, served as a Staff Editor for People Magazine and lived full time as a woman until revealing her trans identity in 2011 in Marie Claire. She had undergone gender reassignment surgery at 18 in Thailand. She is the founder of the #GirlsLikeUs movement and is currently the host of MSNBC's weekly pop-culture show So POPular! 

Buck Angel has the name of a porn star. He also has a giant tattoo that says “pervert,” probably because he is a porn star. But he’s actually a lot more than that. Buck Angel is a transman who, along with a successful career in the industry of adult films, has made a name for himself as an advocate for positive, personal, and sexual self-identity.  He has a documentary about his transition on Netflix called Mr. Angel. Not only is he a rare crossover artist stradeling careers in porn and mainstream media, he's intelligent, well spoken, and cute as a gender queer button. Thank you, sir, may I have another?

Eddie Izzard is the perfect example of “what can’t he do?” in showbiz. He got famous as a stand up, and then came out as a transvestite. Afterwards, he transitioned into film and television, becoming a two-time Emmy award winner. And most recently, he ran 27 marathons in 27 days in commemoration of the 27 years Nelson Mandela spent in prison. Izzard identifies as male, but in the male dominated industry of comedy where homogeny is king, he has the balls to wear a bra. 

Talk about the quirky new girl, Candis Cayne made history on the ABC series Dirty Sexy Money in her role as Carmelita, becoming the first transgender actress to have a recurring role on a prime-time series. Her presence in the drag world is legendary, her contributions to the trans community are great, and her friendship with Caitlyn Jenner has her all up in the docu-series world of I Am Cait right now. Also, cheek bones? Yes, please! 

Jazz Jennings is a YouTube star, but don’t hold that against her. At just 15, she's made a name for herself in the growing movement to acknowledge and support trans youth. She has a docu-series on TLC called I am Jazz, and came out to Barbara Walters in an on-air interview at only six years old as trans. In a world where 40% of all homeless youth are LGBT, perhaps we do need another hero.