3 Historical women who dressed like men

Illustration by Tina Berning 

The escape from slavery of Ellen Craft, a light-skinned mixed-race woman from Georgia, and her husband, William Craft, is known as the most ingenious in fugitive slave history—even more amazing than that of Henry “Box” Brown, who escaped by mailing himself in a wooden crate to abolitionists in Philadelphia in 1849. 

Not much is known about Ellen’s mother, Maria. She is described, like her daughter, as a light-skinned mixed-race slave. This image so innocently describes what can only mean a horrifying lineage of rape and bondage. Ellen was born into slavery when her mother became pregnant by her enslaver, Major James Smith, a lawyer, surveyor, and one of the richest men in central Georgia. Because of her parentage, Ellen was frequently mistaken for white. Major Smith’s wife abhorred Ellen’s presence—she was a constant reminder of his sexual treachery, since Ellen looked more like one of her own children than the child of a slave.  

Ellen was subsequently sent away as a child, which is horrifying, and that new household was where she would eventually cross paths with William Craft. William and Ellen fell in love, and with the permission of their respective “owners,” they married. They knew in their hearts that they did not want to start a family while in bondage, Ellen knowing from experience that her children could be taken from her at any moment. This deep desire to have children—free children—led to a steely-eyed focus on how they might escape. 

Rather than utilising the Underground Railroad, which often meant running in the dead of night, in 1848, when Ellen was 22, she and William decided to flee in plain sight. Knowing that slaveholders could take their slaves to any state, even free ones, fair-skinned Ellen would pose as an infirm white plantation owner and William would pretend to be her enslaved valet, travelling north to Philadelphia. 

William was enslaved by a man who permitted him to work as a carpenter on the side and keep some of his earnings. He used that money to buy men’s clothes for Ellen. William went to different shops, at odd times of the day, and purchased the makings of Ellen’s disguise piece by piece. The night before their escape, William cut his wife’s hair to add to her masculine appearance. In the Crafts’ memoir, Running a Thousand Miles for Freedom (1860), William tells us: “We sat up all night discussing the plan, and making preparations. Just before the time arrived, in the morning, for us to leave, I cut off my wife’s hair square at the back of the head and got her to dress in the disguise and stand out on the floor. I found that she made a most respectable looking gentleman.” 

They set out on their journey on December 21, 1848. Their escape took several days by train and by ship. The pressure that rested on Ellen’s shoulders cannot be overstated for in their escape she had to perform a different race, gender, and class. Although the Crafts had several close calls on their journey, they were successful in evading detection. They arrived in free Philadelphia early on the morning of Christmas Day. As they left the station, Ellen began to cry. They were free. 

Illustration by Tina Berning 

Every woman in my book may be a badass, but not every woman in my book is a hero. In Europe during the sixteenth and seventeenth centuries there was widespread panic about malevolent Satanic witches operating as an organised threat to Christianity. The ongoing inquisitions, which spanned three centuries, saw massive witch hunts, including trials, tortures, and executions at which an estimated 40,000 to 100,000 people were killed. It might be unnecessary to point out, but witches were almost always discovered to be women. 

Between 1661 and 1662, the number of witch trials and executions reached record levels in post-Reformation Scotland, where the number of executions per capita was five times the European average—the majority of which, again, were women. During the height of the witch trials, several methods were used to “prove” that a person was a witch. Perhaps the most chilling method was the practice of witch-pricking.  

Professional witch-prickers (who were, yes, always men) earned a handsome living by unmasking witches, travelling from town to town to perform their ghastly services. The pricker’s job was to test for “the devil’s mark,” a spot where a pin or a needle could be plunged into the body without causing bleeding or pain. But what if the witch-pricker was a woman in disguise? In Scotland in 1662, that’s exactly what happened. A woman named Christian Caddell had watched one of Scotland’s most famous witch-prickers at work and thought to herself, “I could do that!” She went on to reinvent herself as John Dickson, Witch-Pricker. Talk about women not supporting other women. Yikes.

In the end, the tables turned on “John Dickson” when he pointed his pricker at the wrong person, someone who happened to be an influential court messenger. “Dickson” was not only arrested but he himself was then accused of witchcraft (game meet game) and interrogated in Edinburgh in August 1662 on the basis of “false accusation, torture, and causing the death of innocent people in Moray.” Shockingly, when Caddell’s identity was revealed, she was not sentenced to death for her transgressions but was instead deported to a fever-ridden plantation in Barbados and never heard from again. But let the record show that dressing up as a man, pretending to be a witch-pricker, and condemning innocent people to death was considered a lesser offense than being a witch—an entirely made-up thing.

Illustration by Tina Berning 

Legendary African American performer Florence Hines was known as “the queen of all male impersonators.” In 1890, the Indianapolis Freeman called her “the greatest living female song and dance artist.” Hines’s star began to rise in the early 1890s, when she started to receive attention for her performances in Sam T Jack’s Creole Burlesque Company, also known as The Creole Show. The company was wildly popular and toured the United States and Canada, including a stint in Chicago during the 1893 World’s Fair. Although it was produced by Jack, who was white, The Creole Show was a major milestone in Black performance in America because it turned the minstrel format on its head.  

The structure of the show may have been borrowed from the minstrel format, but the stage was no longer filled with white—and sometimes Black—performers in blackface, presenting what was deemed as an authentic depiction of Black life. According to Black theatre historian Marvin McAllister, The Creole Show was “a major outlet for Black artists interested in cultivating non-minstrel material and developing a comedic tradition that was racially grounded but not riddled with stereotyping.” 

The Creole Show, which ran from 1890 to 1897, was innovative for many reasons. One reason lay in who portrayed the role of the “interlocutor,” who was a sort of master of ceremonies. The interlocutor in The Creole Show was performed by a Black woman in male drag: Florence Hines. As interlocutor, Hines performed a routine that was a send-up of the “dandy”—a stylish, modern young man who liked to imbibe and fraternise with women. The songs she sang played up the dandy’s materialism and love of extravagance: “For I’m the Lad That’s Made of Money,” “Hi Waiter! A Dozen More Bottles,” and “A Millionaire’s Only Son.” 

When a white woman played a dandy, she got men in the audience to laugh at themselves or, if it was a working-class crowd, their betters. But when a Black woman played a dandy, it was a subversive act. Hines’s witty and commanding interlocutor was a bold, statement-making departure from the derogatory portrayal of Black men in traditional minstrelsy, and an even further departure from the dim-witted “Mammies” or hyper-sexualised female characters that Black women were so often expected to play. Hines annihilated these stereotypes in her awe-inspiring performance. 

A review in the February 1892 Kansas City American Citizen proclaims that Hines “as a male impersonator is perfection itself. Improvement on Florence Hines’ part is out of the question.” In 1904, the Indianapolis Freeman reported that Hines “commanded the largest salary paid to a coloured female performer.”  

This condensed extract is from Let Me Be Frank: A Book About Women Who Dressed Like Men to Do Shit They Weren't Supposed to Do by Tracy Dawson, with illustrations by Tina Berning 

Read more: 3 Pioneering women who changed history

Read more: 5 Women who changed science forever

Keep up with the top stories from Reader's Digest by subscribing to our weekly newsletter