The best books about cross-dressing

2 authors have picked their favorite books about cross-dressing and why they recommend each book.

Soon, you will be able to filter by genre, age group, and more. Sign up here to follow our story as we build a better way to explore books.

Shepherd is reader supported. When you buy through links on our website, we may earn an affiliate commission (learn more).

She Who Became the Sun

By Shelley Parker-Chan,

Book cover of She Who Became the Sun

This Asian historical fantasy is no simple Mulan retelling, but a deep dive into fate and desire, and the thin line that separates them from each other. Zhu Chongba disguises herself as a male because she decides to steal her dead brother’s destiny of greatness. Though some elements of needing to disguise her gender come up, the story is centered on a strong-willed character’s determination to become exactly who she deserves and wishes to be – a male warrior who takes fate into her own hands to make the world hers. For her, the male appearance is not a disguise, but a destiny. It’s an incredibly powerful story that I couldn’t put down. Parker-Chan is also on the nonbinary spectrum, and writes this queer character with expertise and passion.


Who am I?

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.


I wrote...

Shrouded Loyalties

By Reese Hogan,

Book cover of Shrouded Loyalties

What is my book about?

Naval officer Mila Blackwood is determined to keep her country’s most powerful secret – shrouding, the ability to traverse their planet in seconds through an alternate realm – out of enemy hands. But spies are everywhere: her submarine has been infiltrated by a Dhavnak agent, and her teenage brother has been seduced by an enemy soldier. When Blackwood’s submarine is attacked by a monster, she and fellow sailor, Holland, are marked with special abilities, whose manifestations could end the war – but in whose favor? Forced to submit to military scientists in her paranoid and war-torn home, Blackwood soon learns that the only people she can trust might also be the enemy.

Female Tars

By Suzanne J Stark,

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

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 am I?

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. 


I wrote...

Star-Crossed

By Linda Collison,

Book cover of Star-Crossed

What is my book about?

Patricia Kelley has been raised a proper British lady--but she's become a stowaway. Her father is dead, and her future in peril. To claim the estate that is rightfully hers, she must travel across the seas to Barbados, hidden in the belly of a merchant ship.

The plan works—for a time. Patricia's secret is revealed, and she is torn between two worlds. During the day, she wears petticoats, inhabits the dignified realm of ship's officers, and trains as a surgeon's mate; at night she dons pants and climbs the rigging. And it is there, alongside boson's mate Brian Dalton, that she feels stunningly alive. In this mesmerizing novel of daring, adventure, tragedy, and romance, Patricia must cross the threshold between night and day, lady and surgeon, and even woman and man.

The Perfect Gentleman

By June Rose,

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

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.


Who am I?

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. 


I wrote...

Star-Crossed

By Linda Collison,

Book cover of Star-Crossed

What is my book about?

Patricia Kelley has been raised a proper British lady--but she's become a stowaway. Her father is dead, and her future in peril. To claim the estate that is rightfully hers, she must travel across the seas to Barbados, hidden in the belly of a merchant ship.

The plan works—for a time. Patricia's secret is revealed, and she is torn between two worlds. During the day, she wears petticoats, inhabits the dignified realm of ship's officers, and trains as a surgeon's mate; at night she dons pants and climbs the rigging. And it is there, alongside boson's mate Brian Dalton, that she feels stunningly alive. In this mesmerizing novel of daring, adventure, tragedy, and romance, Patricia must cross the threshold between night and day, lady and surgeon, and even woman and man.

Self-Made Man

By Norah Vincent,

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

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).


Who am I?

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. 


I wrote...

Gender Fraud: a fiction

By Peg Tittle,

Book cover of Gender Fraud: a fiction

What is my book about?

In a near future, 'gender recognition' legislation is repealed, and it becomes illegal for males to identify as females and females to identify as males. However, due in part to the continued conflation of sex and gender and in part to the insistence that gender align with sex, it also becomes illegal for males to be feminine and females to be masculine. A gender identity dystopia.  

Gender Fraud: a fiction was a Finalist for the Eric Hoffer Award 2021.

Masquerade

By Alfred F. Young,

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

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. 


Who am I?

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. 


I wrote...

Star-Crossed

By Linda Collison,

Book cover of Star-Crossed

What is my book about?

Patricia Kelley has been raised a proper British lady--but she's become a stowaway. Her father is dead, and her future in peril. To claim the estate that is rightfully hers, she must travel across the seas to Barbados, hidden in the belly of a merchant ship.

The plan works—for a time. Patricia's secret is revealed, and she is torn between two worlds. During the day, she wears petticoats, inhabits the dignified realm of ship's officers, and trains as a surgeon's mate; at night she dons pants and climbs the rigging. And it is there, alongside boson's mate Brian Dalton, that she feels stunningly alive. In this mesmerizing novel of daring, adventure, tragedy, and romance, Patricia must cross the threshold between night and day, lady and surgeon, and even woman and man.

The Thousand Names

By Django Wexler,

Book cover of The Thousand Names

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.


Who am I?

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.


I wrote...

Shrouded Loyalties

By Reese Hogan,

Book cover of Shrouded Loyalties

What is my book about?

Naval officer Mila Blackwood is determined to keep her country’s most powerful secret – shrouding, the ability to traverse their planet in seconds through an alternate realm – out of enemy hands. But spies are everywhere: her submarine has been infiltrated by a Dhavnak agent, and her teenage brother has been seduced by an enemy soldier. When Blackwood’s submarine is attacked by a monster, she and fellow sailor, Holland, are marked with special abilities, whose manifestations could end the war – but in whose favor? Forced to submit to military scientists in her paranoid and war-torn home, Blackwood soon learns that the only people she can trust might also be the enemy.

New book lists related to cross-dressing

All book lists related to cross-dressing

Bookshelves related to cross-dressing