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

Top 10 Cross Dressers in History

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

Top 10 Cross Dressers in History

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

Top 10 Cross Dressers in History

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

Top 10 Cross Dressers in History

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

Top 10 Cross Dressers in History

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.

5. Shi Pei-Pu

Top 10 Cross Dressers in History

There’s more intrigue in this next case, featuring Chinese opera singer Shi Pei-Pu…the cross-dresser who wasn’t cross-dressing. Shi Pei-Pu was a man,  but when he met junior French diplomat Bernard Boursicot, he told him that he had been born a woman and was living as a man. Bernard Boursicot had previously had affairs with men, but was looking to settle down with a woman, so entered into an affair with Shi who he believed to be a woman dressed as a man.

He wasn’t. He was a man dressed as a man, who was interested in Boursicot for his state secrets. Still, they had a 20-year relationship, during which Shi somehow produced three children. He also passed documents to the Chinese government, containing thrilling secrets such as an order for a cheese grater. They were eventually arrested while living in France, and during their examination it was established that Shi was a man. This was, obviously, news to Boursicot, who heard it over the radio and tried to commit suicide, such was his embarrassment. They both later spent a short period of time in jail and Shi died in 2009.

4. Edward Hyde

Top 10 Cross Dressers in History

Edward Hyde had the rather grand titles of the 3rd Earl of Clarendon, Baron Cornbury and Governor-in-Chief of of New York and New Jersey under Queen Anne. Still, he is chiefly remembered for his fondness of wearing ladies’ clothes, most notably on Queen Anne’s birthday where he dressed as Her Majesty herself. When challenged on this, he said “You are all very stupid people not to see the propriety of it all. In this place and occasion, I represent a woman (the Queen), and in all respects I ought to represent her as faithfully as I can.” He also dressed as a woman for his wife’s funeral, after which he was recalled to England and thrown into jail.

A picture of unknown source (above) is said to be Edward Hyde, but there is nothing concrete to prove this.

3. Colonel Valerie Barker

Top 10 Cross Dressers in History

The theme of women posing as men to join the army is a recurrent one, but one of the longest sustained was Valerie (also known as Lillias) Barker, who posed as her male counterpart Victor for 30 years. Raised as a tomboy by her father, she joined the Canadian army as a woman, but noted how everyone treated her as one of the boys. She had a couple of relationships with men – including a brief marriage to Harold Arkell-Smith – but after one of those relationships broke up she decided to live as a man permanently. She even married a woman, and claimed that her “impotence” was due to war wounds. It was only when she was jailed for bankruptcy that the truth came out. She was released from prison in December 1929. She also used the name “Leslie” when posing as a man, as well as “Bill” briefly. Her multiple names have left a trail of historical confusion behind her.

2. Margaret Bulkley

Top 10 Cross Dressers in History

One of the most successful masquerades in history was that of Doctor James Miranda Barry who was an army surgeon in the 1800s. As a man, Barry went through medical school and a career in medicine without anyone discovering that he was, in fact, a woman. Comments had been made about the “effeminacy” of “his” manner but still, many were shocked to discover her true gender after her death, along with her original name Margaret.

Margaret first assumed the identity of James on a voyage from Ireland with her mother to Edinburgh. Having been abandoned by the men in the family, it seemed prudent to take on a male persona in order to protect her mother in the new country and to go to medical school. She was a very successful and high-profile surgeon, performing one of the first recorded caesarian sections and even her own doctor argued that she was a man. A post-mortem examination, however, showed that she was not only a “perfect female” but also had given birth at some point. An incredible story of deception.

1. Chevalier D’Eon

Top 10 Cross Dressers in History

You have to be someone special to have an -ism named after you and the Chevalier D’Eon was nothing if not special. Male by birth but female by preference, he was known variously as Charles and Charlotte. He was a French diplomat, serving Louis XVI who agreed that he could dress as a woman at court. He later moved to London where he lived mainly as a woman, with Londoners running wagers on his true sexuality. A flamboyant figure and the originator of Eonism, the Chevalier is probably the best known cross-dresser in history.

About the author

Nevzat is a passionate blogger and he loves to share fun weird stories with his blog readers.