The most recommended books about cross-dressing

Who picked these books? Meet our 6 experts.

6 authors created a book list connected to cross-dressing, and here are their favorite cross-dressing books.
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Book cover of Masquerade: The Life and Times of Deborah Sampson, Continental Soldier

Linda Collison Author Of Star-Crossed

From my list on 18th and 19th century crossdressers.

Why am I passionate about this?

The custom of Masquerade, of dressing as Other, has long fascinated me. In writing Star-Crossed, I set out to investigate how and why one girl might pass as a boy in an era when gender roles were sharply differentiated. I once crossed an ocean working aboard a wooden, three-masted ship – a 20th-century replica of the Bark Endeavour, circumnavigating in 1999. Sleeping in hammocks and working aloft in the rigging, I discovered this life required teamwork, stamina – and a sturdy, practical costume. Trousers, not petticoats! I have worked as a registered nurse and I earned a degree in History; these experiences combine in Star-Crossed. 

Linda's book list on 18th and 19th century crossdressers

Linda Collison Why did Linda love 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, and it gives a good picture of colonial life at the time of the American Revolution. 

By Alfred F. Young,

Why should I read it?

2 authors picked Masquerade as one of their favorite books, and they share why you should read it.

What is this book about?

In Masquerade, Alfred F. Young scrapes through layers of fiction and myth to uncover the story of Deborah Sampson, a Massachusetts woman who passed as a man and fought as a soldier for seventeen months toward the end of the American Revolution.

Deborah Sampson was not the only woman to pose as a male and fight in the war, but she was certainly one of the most successful and celebrated. She managed to fight in combat and earn the respect of her officers and peers, and in later years she toured the country lecturing about her experiences and was partially…


Book cover of The Thousand Names

Reese Hogan Author Of Shrouded Loyalties

From my list on cross-dressing women in wartime.

Why am I passionate about this?

As a nonbinary trans guy, I grew up obsessed with novels about women disguising themselves as men. I loved everything about the trope, and always felt disappointed when they had to go back to living as women. It is a trope I eagerly embraced when I wrote Shrouded Loyalties, and though I didn’t yet know the term “transgender,” I was already exploring my own gender identity through my reading and writing of this theme. The books I’ve chosen to highlight here are ones that became some of my very favorites, and also feature action-packed wartime settings like the one used in Shrouded Loyalties.

Reese's book list on cross-dressing women in wartime

Reese Hogan Why did Reese love this book?

The Thousand Names has one of the most unique protagonists and refreshing settings I’ve seen. Winter Ihernglass is disguised as a male soldier in a world of gunpowder and muskets, and ancient demons that can be released with the right magic. I loved watching Winter advance through the ranks and prove her brilliance time and time again. She continues to disguise herself throughout the series, even as women are allowed into the army and more people become aware of her gender, leading me to believe that the look is less a disguise and more her actually living as she truly wants to: as a transgender man in a world that doesn’t yet have a name for it.

By Django Wexler,

Why should I read it?

1 author picked The Thousand Names as one of their favorite books, and they share why you should read it.

What is this book about?

Set in an alternate nineteenth century, muskets and magic are weapons to be feared in the first "spectacular epic" (Fantasy Book Critic) in Django Wexler's Shadow Campaigns series.

Captain Marcus d'Ivoire, commander of one of the Vordanai empire's colonial garrisons, was serving out his days in a sleepy, remote outpost-until a rebellion left him in charge of a demoralized force clinging to a small fortress at the edge of the desert.

To flee from her past, Winter Ihernglass masqueraded as a man and enlisted as a ranker in the Vordanai Colonials, hoping only to avoid notice. But when chance sees…


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

Linda Collison Author Of Star-Crossed

From my list on 18th and 19th century crossdressers.

Why am I passionate about this?

The custom of Masquerade, of dressing as Other, has long fascinated me. In writing Star-Crossed, I set out to investigate how and why one girl might pass as a boy in an era when gender roles were sharply differentiated. I once crossed an ocean working aboard a wooden, three-masted ship – a 20th-century replica of the Bark Endeavour, circumnavigating in 1999. Sleeping in hammocks and working aloft in the rigging, I discovered this life required teamwork, stamina – and a sturdy, practical costume. Trousers, not petticoats! I have worked as a registered nurse and I earned a degree in History; these experiences combine in Star-Crossed. 

Linda's book list on 18th and 19th century crossdressers

Linda Collison Why did Linda love 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 in official naval records, but were there, a part of history. 

By Suzanne J Stark,

Why should I read it?

2 authors picked Female Tars as one of their favorite books, and they share why you should read it.

What is this book about?

For a very long time now I have delighted in histories, letters, records, and memoirs to do with the Royal Navy in the eighteenth and early nineteenth century; but Suzanne Stark's book has told me many, many things I did not know, and I shall keep it on an honored shelf."--Patrick O'Brian

The wives and female guests of commissioned officers often went to sea in the sailing ships of Britain's Royal Navy in the 18th and 19th centuries, but there were other women on board as well, rarely mentioned in print. Suzanne Stark thoroughly investigates the custom of allowing prostitutes…


Book cover of The Perfect Gentleman

Alina Rubin Author Of A Girl with a Knife

From my list on making you glad for modern medicine.

Why am I passionate about this?

Stuck at home during the pandemic, I started watching historical fiction and fell in love with the British miniseries, Hornblower. Suddenly I found myself writing my own stories about an imprisoned midshipman and Ella Parker, a surgeon that saves him. But there was a plot hole. Women could not be doctors in 19th-century England, leave alone ship surgeons. Thus, I sent Ella into medical school disguised as a man, and Hearts and Sails series was born. Looking for interesting cases for Ella to observe and treat, I became obsessed with the history of modern medicine. I also wanted my character to overcome great obstacles and eventually prove to others what a woman can do.

Alina's book list on making you glad for modern medicine

Alina Rubin Why did Alina love this book?

I’m often asked if Ella Parker is based on Dr. James Barry. She’s not. But I was glad to confirm that history recorded at least one woman was able to disguise herself as a man and become a distinguished doctor. The biography of Dr. Barry is intriguing, well-written, and shows how brilliant and mysterious an individual he was. The best find for me was the list of classes Barry attended at the University of Edinburgh. I sent my main character into the same classes, including the optional midwifery, and the private class with a prestigious teacher. This biography gave me many answers about this remarkable doctor, but also left me with questions. 

By June Rose,

Why should I read it?

2 authors picked The Perfect Gentleman as one of their favorite books, and they share why you should read it.

What is this book about?

James Barry was one of the most outstanding doctors of the nineteenth century – a brilliant surgeon, a tireless campaigner for medical reform, and a compassionate Inspector-General of the Army.

But throughout a long and distinguished career an air of secrecy, even of scandal, always clung to Barry. The shrill voice, the diminutive build, the almost ostentatious humanity – all struck a discordant note in the stiff, conventional world of the officers’ mess. Only after the doctor’s death in 1865 did the incredible truth come to light:

Dr. James Barry was a woman.

What was her real identity? How did…


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

Peg Tittle Author Of Gender Fraud: a fiction

From my list on to make you think about gender and sex.

Why am I passionate about this?

I am the author of several novels—in addition to the one featured here, Impact, It Wasn't Enough (Finalist for the Eric Hoffer Award), Exile, and What Happened to Tom (on Goodreads' "Fiction Books That Opened Your Eyes To A Social Or Political Issue" list).  I was a columnist for The Philosopher Magazine for eight years, Philosophy Now for two years, and the Ethics and Emerging Technologies website for a year ("TransGendered Courage" received 35,000 hits, making it #3 of the year, and "Ethics without Philosophers" received 34,000 hits, making it #5 of the year), and I've published a collection of think pieces titled Sexist Shit that Pisses Me Off. 

Peg's book list on to make you think about gender and sex

Peg Tittle Why did Peg love 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).

By Norah Vincent,

Why should I read it?

1 author picked Self-Made Man as one of their favorite books, and they share why you should read it.

What is this book about?

Following in the tradition of John Howard Griffin (Black Like Me) and Barbara Ehrenreich (Nickel and Dimed), Norah Vincent absorbed a cultural experience and reported back on what she observed incognito. For more than a year and a half she ventured into the world as Ned, with an ever-present five o'clock shadow, a crew cut, wire-rim glasses, and her own size 11 1/2 shoes-a perfect disguise that enabled her to observe the world of men as an insider. The result is a sympathetic, shrewd, and thrilling tour de force of immersion journalism that's destined to challenge preconceptions and attract enormous…