Top 10 Historical Figures Known For Wearing Clothes of the Opposite Sex

10:00 am 8 Apr, 2013

Cross dressing of men as women and women as men has been in process since time immemorial. The men and women have cross dressed to take up new roles, responsibilities, to hide their identities or simply for the sake of being different. While there are many examples of historical figures known to have worn clothes of their opposite sex to take up different roles and identities, here we have listed top 10 of such historical figures who have been known to wear clothes of the opposite sex.

10. Stanislawa Walasiewicz:

Polish Olympian and US athlete and sprinter, Stanislawa Walasiewicz or Stella Walsh as she was better known, had been one of the very successful female athletes. It was however revealed at her death that she had actually been a man, disguised as woman in clothing (there really weren’t any gender tests for athletes then). Not really a man though, Stella Walsh had mosaicism, that gave her ambiguous genitalia.

Stanislawa Walasiewicz - Historical Figures Known For Wearing Clothes of the Opposite Sex

9. Anne Bonny and Mary Read:

Raised as a boy Mary Read was once travelling by ship was captured by pirates, she was really fascinated by pirates and decided to become one. She joined the crew of another female pirated Anne Bonny and together they gained a lot of significant notoriety as male disguised female pirates. The two (along with their male crew) were captured in 1720, only to become first two women ever to be convicted of piracy.

Anne Bonny and Mary Read - Historical Figures Known For Wearing Clothes of the Opposite Sex

8. Deborah Sampson:

There aren’t many women who have fought brave battles, but Deborah Sampson was a little different. In the American Revolutionary War, Sampson fought disguised as, and in name of her deceased brother. It wasn’t known she was a female until she was hospitalized the second time because of war injury.

Deborah Samson - Historical Figures Known For Wearing Clothes of the Opposite Sex

7. Billy Tipton:

Billy Tipton born as Dorothy Lucille Tipton in 1914 was so fascinated being a man that 16 years later, in 1930 she began to live like a man. Known best as Billy Tipton hence, he was married five times and had three adopted kids. It’s believed that none other than his birth family, until his death, knew of his cross dressing and cross living.

Billy Tipton - Historical Figures Known For Wearing Clothes of the Opposite Sex

6. Pope Joan:

There haven’t been many female Popes; therefore this one does go down as an epic. It is alleged that Pope Joan was female pope who disguised and dressed like a man and reigned from 855 to 858. Historians in the modern era regard her as a mystical figure of the 13th Century who originated from the anti-papal satire.

Pope Joan - Historical Figures Known For Wearing Clothes of the Opposite Sex

5. Amandine-Aurore-Lucile Dupin:


Another women who really fancied being dressed as a man, and living the cross identity all her life was Amandine-Aurore-Lucile Dupin – French novelist of the 19th century. She liked writing under the pseudonym name George Sand and preferred to wear men’s clothing. Dupin has vividly explained her experience of cross dressing in her autobiography.

Amandine-Aurore-Lucile Dupin - Historical Figures Known For Wearing Clothes of the Opposite Sex

4. Emperor Elagabalus:

I didn’t know a Roman Emperor who preferred to dress up like a women, until I read about Elagabalus. Elagabalus was made Emperor at the age of 14, during his reign he wore make up and dressed like a woman. It is alleged that he referred to his chariot driver Hierocles as his husband. It is also believed that he offered to pay money to doctors to make him a female biological. Now, I just wish the Roman Empire lived to the 21st century and Elagabalus was the emperor now, his wish would have been granted.

Elagabalus - Historical Figures Known For Wearing Clothes of the Opposite Sex

3. Shi Pei-Pu:

Male Peking Opera or Beijing Opera singer, Shi Pei Pu can be termed as real life James Bond and master of disguise. Spying on behalf of the Chinese Government, he convinced Bernard Boursicot, a French diplomat that he was actually a woman dressed as man. The two are believed to have married for 20 years. It is alleged that Boursicot even started providing secret documents to the Chinese for Shi.

Shi Pei-Pu - Historical Figures Known For Wearing Clothes of the Opposite Sex

2. Catalina de Erauso:

The brave Catalina de Erauso also known as La monja alferez (or the nun lieutenant) was a Spanish female officer who enrolled as soldier in the Spanish army under the name Alonso Díaz Ramírez de Guzmán. She served under various captain, including her own brother, but here identity was never discovered. She was a brave soldier disguised as man and was very famous in America until she confessed her reality to a Bishop, well before her death.

Catalina de Erauso - Historical Figures Known For Wearing Clothes of the Opposite Sex

1. Joan of Arc:

If we know history, we for sure know Joan of Arc. For others, Joan of Arc was a French heroine and Catholic saint, who joined the French army to fight the British forces in France. On being captured by the English, Joan was burned at the stake. She was convicted by the religious court of dressing in male clothing (a major reason for her execution). But it is believed that Joan of Arc said, ‘she wore male clothing because she feared the guards would rape her.

Joan of Arc - Historical Figures Known For Wearing Clothes of the Opposite Sex

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