Top 10 Cross Dressers in History

5. Shi Pei-Pu

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

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

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

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

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.

Leave a comment

Your email address will not be published. Required fields are marked *