Top 10 Historical Cross Dressers


Dressing as a member of the opposite sex has a long and varied history. In the past, men and women cross-dressed to assume new roles, to enable them to do things they otherwise couldn’t, or because they just plain wanted to. Here are some individuals who for whatever reason decided to adopt the clothing of the opposite sex:

10. Mary Read, Pirate (1690 – 1721)

Ann Bonny and Mary Read

Ann Bonny and Mary Read

Raised as a boy by her mother in England, Read joined the British military at a young age. On a trip to the West Indies, the ship she was traveling on was captured by pirates, and Read decided that a pirate’s life was for her. When she later joined a new crew, a female pirate by the name of Anne Bonny took a liking to her. In a scene straight out of a movie, Bonny attempted to seduce Read, only to discover that she, too, was a female pirate. The two became lifelong companions. After being captured in 1720, Read and Bonny became the only two women to ever be convicted of piracy.

One story tells of Read winning a duel by ripping her shirt open, and then taking advantage of her opponent’s surprise to defeat him.

9. Elagabus, Emperor (204 – 222 AD)

Elagabus was made Emperor of Rome at the age of only 14, after successful political maneuvering by his maternal aunt. During his reign as Emperor, he preferred women’s dress. He had his whole body depilated, wore makeup, and referred to his chariot driver Hierocles as his husband. He even made an offer of money to any doctor who could perform surgery on him to make him biologically female.

None of this exactly made him popular in the highly traditional Rome of the time. His popularity also wasn’t helped by the fact that Elagabus married a priestess who’d been sworn to virginity, and instituted controversial sun-worshiping religious practices. He was assassinated in 222, at the age of only 18.

8. Francois De Choisy, Writer (1644 – 1724)

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French author Francois De Choisy was dressed as a girl by his mother until the age of 18. Her reasons might have been political: De Choisy’s playmate, Philippe I, was also encouraged to dress as a girl, possibly so that he would not be seen as posing a threat to his older brother, King Louis XIV. As an adult, De Choisy took up male dress for a while but soon went back to his preferred female clothing. Many young women of the day visited him for fashion advice, encouraged by their mothers. He enjoyed their company: so much, in fact, that one ended up pregnant by him. Although he later wrote a number of historical and religious works, De Choisy is most famous for his tell-all book The Transvestite Memoirs, published in 1737.

7. Queen Christina of Sweden (1626-1689)

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Christina’s father wanted to make sure his daughter was tough enough to rule, and so gave her a ‘masculine’ upbringing: her favorite childhood hobby was bear-hunting. Christina assumed the throne at age 18, but abdicated only ten years later under increasing pressure to marry and produce an heir. Instead, she left Sweden dressed as a man, a practice she continued on and off for the rest of her life. She converted to Catholicism and moved to Rome, where she received special permission to dress in men’s clothing. She is one of only two women ever buried in St Peter’s Church in Rome.

6. Deborah Samson, Soldier (1760-1827)

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At the age of 21, Samson dressed in men’s clothing and enlisted to fight in the American Revolutionary War under the name of her deceased brother. Things went remarkably smoothly until she was wounded in battle: Samson was so scared of being found out that she instructed her fellow soldiers to leave her on the field to die, but they refused. She escaped from the hospital, and removed a bullet from her own thigh. Another hospitalization in 1783 finally revealed her secret, and Samson was given an honorary discharge. Although she later married and had children, Samson did several speaking tours wearing her old military uniform. She was the first known American to pass as a male in war, but definitely not the last. Up to 400 women are thought to have fought in the Civil War while dressed as men.

5. Charles D’Eon, Diplomat (1728 – 1810)

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A French soldier, spy and diplomat, D’Eon was sent to Russia in 1756 to reestablish diplomatic relations between the countries: he achieved this by dressing as a woman and becoming a maid of honor to the Russian Empress. Later, he worked as an ambassador in London, where at one point there was so much speculation on whether he was male or female that people actually placed bets on the London Stock Exchange. On his return to France, D’Eon demanded that he be recognized as a woman, claiming that he had in fact been born female and raised as a boy because of an inheritance dispute. The French King agreed, providing that he wear ‘appropriate’ women’s clothing. Posthumously, medical examinations revealed D’Eon to be anatomically male.

4. Marina the Ascetic, Monk (Fifth Century)

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Marina was born in modern-day Lebanon. When her father wanted to join a monastery, she insisted on coming with him, dressing as a man and taking the name Marinos. After her father’s death, a girl who lived near the monastery fell pregnant and accused Marinos of seducing her. When confronted, Marinos did not deny the allegations out of a desire to not embarrass the girl. The disgraced monk was forced to live outside the monastery and raise her accuser’s child for many years. When she died at around age 40, she was finally discovered to be female. Her former accuser confessed to the lie.

Marina is only one of dozens of women throughout history thought to have entered religious life posing as men. There is even a story of an undercover female Pope, Pope Joan, although that one at least has no historical basis.

3. Isabelle Eberhardt, Explorer (1877 – 1904)

 Isabelle Eberhardt (17 February 1877 — 21 October 1904)

Isabelle Eberhardt (17 February 1877 — 21 October 1904)

Born in Switzerland, Eberhardt moved to North African in 1897, where she became an explorer under the assumed name of Si Mahmoud Essadi. Male clothing allowed her to move freely in Arab society, and she eventually joined the Sufi sect Qadiriyya, impressing them so much with her piety that she was initiated as a faqir, a male member of the order. During her short life, she also acted as a spy and briefly took up arms in an Algerian revolt against France.

2. Shi Pei-Pu, Spy (1938 – 2009)

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Male opera singer Shi Pei-Pu met Bernard Boursicot, an employee at the French Embassy in Beijing, when Shi was 26. After convincing Boursicot that he was actually a woman dressed as a man, they began an affair. Amazingly, the charade continued for 20 years, with Shi at one stage claiming to have borne him a son. Boursicot even began handing over secret documents to the Chinese in order to help Shi’s position in the Communist party. In 1982, Boursicot brought Shi and his son to Paris, where they were eventually arrested for espionage. When Shi’s identity was revealed, Boursicot physically attacked him, slashing his throat. Shi survived. A successful play and then movie, M. Butterfly, was loosely based on Shi’s life.

1. Joan of Arc, Soldier (1412 – 1431)

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During the Hundred Years War, when large areas of France were occupied by the English, this young peasant girl heard heavenly voices commanding her to cut her hair, dress as a man, and go lead an army. Joan convinced Charles VII, the French claimant to the throne, that she was for real, and was given an army and supplies. She led a series of military successes that ended with Charles being crowned King.

At the age of 19, Joan was captured and handed over to a pro-English Bishop, who subjected her to an illegal trial. In Europe at the time, cross-dressing was actually condoned, providing that a woman did it for safety or protection. Nevertheless, Joan was convicted of ‘relapsed heresy’ when she took up male dress again in prison, probably after a rape attempt. She was burned at the stake. Later, the unjust decision was overturned in court, and Joan is now considered a saint by the Catholic Church and a heroine of France.

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  1. Ladies and gents……there will ALWAYS be someone that didn’t make the cut. Even historically, I’m sure that there are way too many crossdressers to count and since this isn’t ….someone will always be disappointed.

    I must say that Shi Pei-Pu was a good one though. I had to research more on that lol….that story is hard to believe…

  2. You should have at least mentioned Bonnie Prince Charlie who fled to the Isle of Skye and then to Europe after the Battle of Bannockburn dressed as a woman.

    • That should have read Battle of Culloden, not Bannockburn. A mere oversight in proof reading on my part

  3. I’d have liked less people that cross-dressed for a purpose and more that did it out of personal preference.

    No list of this nature is complete without Ed Wood, and possibly (depending on whom you believe) J. Edgar Hoover.