The Humanity of Playing With Gender: An Abridged History of ‘Cross-Dressing’

As transphobic folks scream sentiments into the void about there “only being two genders” and ideas (not supported by science OR history) surrounding the perceived, stagnant nature of gender in relation to assigned birth sex, it’s often ignored that gender roles are ever-changing, and playing with opposite-gender and opposite-sex roles and presentation is an ancient practice, recorded throughout centuries of history.

“Cross-dressing” is plainly the practice of wearing clothes of the opposite sex or gender. In today’s terms, it’s often not so simply defined, as folks of all genders work to degender fashion, recognizing that the idea that a garment is inherently “feminine” or “masucline” is solely a societal fabrication. 

It’s more about the act itself, which is usually more fleeting, potentially for comfort, power, sex appeal, or self-expression, not a state of being; so while history sometimes has a hard time with the distinction between people who cross-dress and trans and gender-nonconforming folks, people dressing to affirm their correct gender identity is not what we’re referencing here.

In the ancient world, cross-dressing often mirrored the gender-crossing actions of deities. In this context, it was not only tolerated, it was often supported as an act of religious and spiritual devotion. Many cultures associated this transformation of gender with coming closer to divinity by deconstructing the categories surrounding the human experience.

One of the best-known examples of early gender-bending was Dionysus, who Greek literature scholar Albert Henrichs called the “most versatile and elusive of all Greek gods,” often perceived as human and animal, male and female, young and old. Depictions of Dionysus range from a more masculine, bearded version, to more feminine versions, with a woman’s tunic and saffron veil. Dionysian festivals also frequently featured role reversals that included opposite-gender dress.

The Sumerian deity Inanna is believed to be capable of either gender presentation to bridge heaven and Earth with gender-altering power. Atum of Ancient Egypt was also depicted androgynously, as said in coffin text, “I am the great He-She.” The earliest recorded historical woman to dress and act like a man was Hatshepsut, an Egyptian from about the 5th century B.C.E., portrayed in a statue wearing a symbolic, royal beard.

And we all know the story of Hua Mulan, which has existed since the sixth century C.E., when a poem called “The Ballad of Mulan” was written.

The story of Mulan also calls out to the history of women dressing as men, a practice that spans history and culture, to gain social power and privileges women didn’t have, shedding light on the lack of equity and more stringent gender roles surrounding womanhood. Women fought as men on both sides of the Revolutionary War, and at least 400 Civil War soldiers were women dressed as men. In that same era, ordinary women would wear mens’ clothing to obtain higher wages.

Joan of Arc famously fought in a man’s military uniform in the 15th century; George Eliot and the Brontës took up masculine pen names to be published and taken seriously. 

History sometimes conflates these women with early trans men from history, but the distinction is that these people were typically not dressing to affirm their correct gender but to expand the societal confines surrounding womanhood. Writer Hilary Mantel recently cautioned against imposing a trans narrative on these people—the belief that women who defied the odds to live fuller lives were simply trans men—pointing, rather, to the very binary confines of gender and the persistent human desire to dismantle those constructs early on.

Of course, there’s the famed Shakespeare era of theater, which sometimes mirrored these very acts in performance (of Shakespeare’s 38 surviving plays, seven featured “cross-dressed” characters, often a female character adopting a male identity for protection and existing in a sort of middle-ground gender category).

Women were also not allowed to perform on stage in Elizabethan England, so men were not only dressing as and playing female characters, but they would also play these roles, essentially a man pretending to be a woman, who is also pretending to be a man.

Just about 100 years later, “molly-houses,” male brothels, became part of queer subculture in England, “Molly” referring to a gay man. Employees and patrons often engaged in cross-dressing, even though they could be (and often were) severely prosecuted for it.

In the mid-18th century, laws began spreading to criminalize cross-dressing. One of the oldest laws, dating back to 1845 in New York, said it was a crime to have your “face painted, discolored, covered, or concealed, or (be) otherwise disguised (while) in a road or public highway.” It was initially intended to punish rural farmers who would dress as Native people to fight off tax collectors, but by the beginning of the 20th century, with the increasing belief that “gender inappropriateness” was a public offense, law enforcement began applying these laws (“masquerade laws”) to opposite-gender dress, even if the laws didn’t specifically mention it.

It mirrors the influx of legislation we see today, trying to criminalize the sheer presence of gender variance. “If we don’t like it, then maybe we can just outlaw it and it’ll go away.”

The U.S. fear and panic over LGBTQ people escalated through the 20th century, and arrests revolving around 19th-century masquerade laws became more commonplace. This is where the line begins to blur, as trans people, gender-nonconforming people, drag performers, and cross-dressers were essentially treated the same by law enforcement and the world at large. It was all “wrong” in their eyes, with the larger aim of policing gender-expansive expression beyond the cisgender binary.

As this reached a head through the 60s, a regular police presence at queer spaces leading to violent arrests and sexual humiliation namely in the New York scene, the 1969 Stonewall Riots changed everything. While arrests continued after the riots, they became much less widespread.

Though it’s been more than 50 years since Stonewall, and the confines of a print column can’t begin to fully dive into the dense history of people blurring gender roles, expression, and expectations, we’re still fighting against these same ideas. The gender binary and gender expression is touted as some kind of hard fact, and those who dare to question these fabricated ideas are deviants.

Even our ancestors from centuries past had that distinct need to move past a stringent, two-category system that often keeps us from pursuing a full, authentic experience on this planet. If we resonate in those ancient beliefs, those early religions, we might take a note from history and recognize the ideas around the “feminine” and “masculine” expression are inherently human and not exclusive to any gender.