The best books about 18th & 19th century crossdressers

Perhaps the most famous of the 18th-century crossdressers is Hannah Snell. Hannah was a British woman who passed as "James Gray" and became a marine in the Royal Navy, following the death of her infant daughter. During her military career of more than four years she was wounded in battle and later was officially recognized and pensioned for her service. Hannah's is only one of at least twenty authentic accounts of females serving aboard Royal Navy ships, according to editor Tom Grundner, who writes the preface to The Lady Tars; the Autobiographies of Hannah Snell, Mary Lacy and Mary Anne Talbot. Three entertaining, informative accounts in one book.

The notable Victorian physician, Dr. James Barry, was born female. Aided by her family, she passed as a young man in order to enter the University of Edinburgh to study medicine. Barry's true parentage remains unverifiable, but a good deal is known about the doctor's long career as a British Army Surgeon. Dr. James Barry is remembered for improving conditions for wounded soldiers, reforms in hygiene (revolutionary, at that time), and for performing one of the early successful caesarian surgical deliveries, in which both mother and infant survived. There have been several biographies written about Barry but June Rose's The Perfect Gentleman cuts to the known basics of Barry's life in a straightforward, interesting story.

It took Americans a very long time to honor the ordinary foot soldiers and seamen of the Revolution. It took even longer to recover the women of the Revolution, historian Alfred F. Young tells us. The author parses through various historical records to present a realistic picture of the female soldier Deborah Sampson. Deborah was not the only woman to volunteer as a soldier – dressed as a man. Her record was exemplary. Sampson became known only after the war was over, and then only to a few people. This biography is among the most thorough of crossdressing fighting women, and it gives a good picture of colonial life at the time of the American Revolution. 

This was the first nonfiction book I read that fired up my interest and started my research for my own historical novel. Stark gives a picture of the females to be found aboard ships in the British Royal Navy, most of whom were not posing as men but were wives of warrant officers. One chapter is devoted to women in disguise in naval crews. The last chapter is devoted to the crossdresser Mary Lacy, who passed as William Chandler, and worked as a shipwright. With illustrations and endnotes, Female Tars sheds light on the women who are seldom mentioned in official naval records, but were there, a part of history. 

Who was s/he – a man, a woman masquerading as a man, or a gender fluid person?

The Chevalier d'Eon was a French courtier and diplomat, decorated military officer, writer – and a cross-dressing spy for Louis XV in a clandestine foreign policy organization known as the Secret du Roi. A well-researched account, Kates' political "thriller" is quite unlike any other crossdresser's biography I've read; it kindles a conception of 18th-century gender fluidity that reflects perception, influence, and political power in a European age when clothes indeed, made the man.