It’s a wonderful thing to live in a world where it is slowly becoming more and more accepting to feel free to dress and express yourself regardless of your biological sex. With celebrities such as Harry Styles, Ruby Rose, Nico Tortorella, Tilda Swinton and Cara Delvigne who are consistently seen and photographed wearing fashion that challenges traditional gender roles, it’s easy to think that this is a modern phenomenon when in fact, it’s been around for quite a while. Throughout history there are heaps of examples of celebrities and historical figures who either cross dressed, transitioned between genders and presented as a different gender than the one they were originally assigned at birth. When I started putting this article, I wanted to keep the list mainly focusing on the 1900’s to about the 1950’s but there’s a wide range of how celebrities have challenged gender. This particular post looks at vintage celebrities who challenged gender roles through their fashion and some who eventually transitioned. I hope in future posts to write about famous films featuring cross dressing genders, androgynous celebrities and transsexual celebrities so stay tuned for some of those in the near future.

Marlene Dietrich
The German star is famous for her captivating voice and distinct masculine-preferencing style (who looks absolutely fabulous in this below image from the 1940’s). Dietrich, who was also quite public about her fluid sexuality, famously wore a tuxedo in 1930’s Morocco, and blazed the trail for making menswear sexy for women onscreen. After the film, she often wore more masculine outfits which today is considered her iconic look.

Katherine Hepburn
Katharine Hepburn is another revolutionary of suit-wearing from the 20th century. Along with Marlene Dietrich, Hepburn helped to shift the view of trousers on women from a garment of necessity into a garment of fashion. She also fancied men’s haircuts and makeup, typical for those times. Hepburn famously upset her Hollywood executors who warned her not to wear pants around the filming lot or they would get rid of them; after she was spotted wearing pants again, her pants were removed from her trailer. Hepburn left her trailer with only her underwear covering her lower half. Epic.

Louise Brooks
Considered one of the first female divas of the modern century wearing men’s clothes in the cinema, is Louise Brooks. She became a style icon of the 1920s and spokesperson of a free and uninhibited femininity. Brooks played a lot about her sexual ambiguity, even off the screen.

Claude Cahun
Born Lucy Schwob, Surrealist artist Claude Cahun adopted her androgynous pseudonym in 1917. Called “one of the most curious spirits of our time” by André Breton, her work challenges identity through self-portraiture. With her lover Suzanne Malherbe (who went by Marcel Moore), Cahun also created anti-Nazi propaganda during WWII.

Edward D. Wood Jr.
After Christine Jorgensen’s headline-making surgery in 1952, Ed Wood Jr. wrote, directed, and starred in Glen or Glenda (1953). An enthusiastic cross-dresser himself, Wood’s film features a psychiatrist narrating the stories of Glen/Glenda, a closeted heterosexual transvestite, and Alan/Ann, a pseudo-hermaphrodite who identifies as a woman. Despite being described by Leonard Maltin as “possibly the worst movie ever made,” Glen or Glenda has become a cult classic. Its production is chronicled in Tim Burton’s Ed Wood.

Christine Jorgensen
With the New York Daily News headline “Ex-GI becomes Blonde Beauty” in 1952, Christine Jorgensen became the first widely known transsexual. Gender reassignment surgery had been pioneered in Germany in the twenties, but Jorgensen was the first to go public. Beginning her transition with hormone therapy in Copenhagen, she completed surgical reassignment in the states. A lifelong advocate for transsexuals, Jorgensen helped educate the public on the difference between gender identity and sexual preference.

Billy Tipton
Born Dorothy Lucille Tipton, jazzman Billy Tipton lived for more than 50 years as a male. Billy never legally married but, over the years, as many as five women identified as “Mrs. Tipton.” He told his wives that a catastrophic car accident had left him sterile. With the fifth, Kitty Oakes, he raised three adopted sons. A funeral director finally revealed Tipton’s secret to his family. One of his sons remarked: “He’ll always be Dad to me.”

Radclyff Hall
Well-born lesbian and English poet Radclyffe Hall assumed her father’s name and favoured short hair, bow ties, and smoking jackets. Borrowing the terminology of sexologist Richard von Krafft-Ebing, Hall considered herself a “congenital invert” with a “masculine soul, heaving in the female bosom.” Her 1928 novel, The Well of Loneliness, which mirrors her own life, was deemed obscene and all copies were ordered destroyed.

Keeping the list to those who emerged between 1900 and 1950 means that more modern celebrities were unfortunately omitted from this list but I would love to put together a part two very soon. These celebrities were figures that defied social norms and stood up for change in gender roles throughout a time where such actions were often met with violence, loss of work, shame and much more. Celebrities today who challenge gender roles have been able to do so with these iconic figures first paving the way. If there’s a celebrity that I should add to this list please let me know.

Note: This is not a sponsored post. All opinions and thoughts expressed are solely my own and not influenced in any way. There are no affiliate links and I do not benefit from any link clicks or purchases made.