The best books about cross-dressing 📚

Browse the best books on cross-dressing as recommended by authors, experts, and creators. Along with notes on why they recommend those books.

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Book cover of Female Tars: Women Aboard Ship in the Age of Sail

Female Tars: Women Aboard Ship in the Age of Sail

By Suzanne J Stark

Why this book?

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…

From the list:

The best books about 18th & 19th century crossdressers

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Book cover of The Perfect Gentleman: The Remarkable Life of Dr. James Barry

The Perfect Gentleman: The Remarkable Life of Dr. James Barry

By June Rose

Why this 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…

From the list:

The best books about 18th & 19th century crossdressers

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Book cover of Monsieur D'Eon is a Woman: A Tale of Political Intrigue and Sexual Masquerade

Monsieur D'Eon is a Woman: A Tale of Political Intrigue and Sexual Masquerade

By Gary Kates

Why this book?

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.

From the list:

The best books about 18th & 19th century crossdressers

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Book cover of Masquerade: The Life and Times of Deborah Sampson, Continental Soldier

Masquerade: The Life and Times of Deborah Sampson, Continental Soldier

By Alfred F. Young

Why this book?

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,…

From the list:

The best books about 18th & 19th century crossdressers

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Book cover of Self-Made Man: One Womans Journey into Manhood & Back Again

Self-Made Man: One Womans Journey into Manhood & Back Again

By Norah Vincent

Why this book?

Reading much like a novel, Vincent's book is a first-person account of a woman going undercover as a man (cross-dressing drag rather than trans, per se) to discover what men are like: "I found masculinity distilled, unmitigated by feminine influences, and therefore observable in a concentrated state" (p181).  An intriguing contrast to Schilt's book, Vincent says "It was hard being a guy" (p275); "Someone is always evaluating your manhood" (p276); "I saw how degraded and awful a relentless, humiliating sex drive could make you" (p277).

From the list:

The best books to make you think about gender (and sex)

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