Top 10 Cross Dressers in History

Think that cross-dressing is a modern phenomenon? You could not be more wrong. It only takes a quick breeze through some Shakespeare plays to see that people cross-dressed all the time – and in those days, apparently sticking a false beard on was not only an effective disguise but also caused women to fall in love with you. And if you’re part of a pair of girl/boy identical twins, the potential for chaos is almost unlimited once you stick a dress or a pair of breeches on.

But it also happened in real life. Whether it was because of gender confusion or for practical/career-minded reasons, people have often cross-dressed and sometimes it’s only been after their deaths that their true gender has been revealed. So don a wig of your choosing and enjoy our Top 10 Cross Dressers in History.


10. Joan of Arc

Probably the most famous of our list, Joan dressed as a man in order to lead the French army into battle, a job that just wasn’t deemed fit for a woman to do. As a 12-year-old girl in rural France, she had been receiving visions from past saints and became convinced that her destiny was to free France from the English invaders. She was rejected as a woman, but dressed as a man and petitioned Charles VII directly to be allowed to fight. Surprisingly, he allowed the farm girl to lead his armies and she won some great victories, although she never fought directly. She was later burned as a heretic and the charges were partly due to her “male attire”, which was said to be disrespecting the laws of God and nature.


9. Frances Clayton

Another woman who cross-dressed to go to war, Frances Clayton disguised herself as a man and served on the Union side in the American Civil War alongside her husband Elmer. According to one account, he was killed in front of her at the Battle of Stones River and she stepped over him to carry on fighting.

Her disguise was fairly effective – she took care to swear, smoke and gamble, none of which would have been acceptable for a lady of the time. There is some murkiness over how she was discovered – some say she confessed to her commanding officer and was dismissed, while others say she was wounded in the hip and so was revealed that way. But it is sure that she, along with other women who did something similar in the Civil War, proved just how brave women could be.


8. Dorothy Tipton

It’s not just the military that has been traditionally male-dominated. The world of jazz music was also hard for a woman to break into, hence Dorothy Tipton performing as a man named Billy. Binding her breasts and dressing as her male alter ego Billy, Dorothy soon began living as a man in private too, and by 1940 was effectively a man. Only a few relatives knew her secret and even girlfriends she lived with believed that she was male.

One such girlfriend was Betty Cox. “Billy” told Betty that he had sustained rib and genital injuries in a car accident and so had to bind them at all times. We can assume the relationship was never properly consummated, but in all other senses they had a heterosexual relationship. Tipton later settled down with Kitty Kelly, a stripper, and they adopted three boys. It was only after her death that Dorothy was revealed to have been female all along.


7. Hercules

Of course, not all historical figures are, strictly speaking, historical. And so it is with Greek hero Hercules, also known as Heracles, who appears in mythology performing tasks of amazing strength and courage. One of which included cross-dressing. As punishment for the murder of Iphitus, Hercules was enslaved to Omphale, Queen of Lydia. She made him perform what would be traditionally women’s tasks and dress as a woman while doing it. A surviving mosaic (above) shows Hercules holding a basket of wool, dressed as a woman, while Omphale wears his lion skin and carries his club. An early (and probably apocryphal) subversion of gender roles.


6. Ulrika Eleonora Stålhammar

Another example of a soldier that turned out to be a woman was Vilhelm Edstadt, aka Swedish woman Ulrika Eleonora Stålhammar. The daughter of a soldier, she found herself orphaned and penniless, so dressed in her father’s clothes and went to join the army in order to avoid a forced marriage. She later fought in the Great Northern War against Russia (above)

She also married a woman, Maria Löhnman, but the marriage remained happy even after she revealed her true sex. The pair were later publicly revealed and charges with crimes against God – Ulrika for posing as a man and Maria for homosexuality – but received only short jail sentences due to the chaste nature of their relationship, and lived the rest of their lives peacefully.

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