A Letter to Jemima Wilkinson (November 29, 1752 – July 1, 1819)
Dear Public Universal Friend,
In 1776, clothing was never just fabric…
It was law.
Class.
Religion.
Gender.
Authority.
Permission.
A coat could open doors.
A dress could close them.
A hat, boot, or pair of trousers silently announced where society believed you belonged.
And stepping outside those expectations carried risk.
Because colonial America depended heavily upon visible order. People were expected to look the part society assigned them:
men masculine,
women feminine,
servants modest,
elites refined.
Identity itself was supposed to remain legible.
So when someone crossed those visual boundaries, society reacted with fascination, suspicion, fear, curiosity, or punishment depending entirely on circumstance.
And there you stood, Public Universal Friend, one of the most extraordinary figures of Revolutionary America, rejecting both male and female identity after a near-death illness and emerging into public life dressed in androgynous clothing while refusing gendered pronouns altogether.
In the 1770s…
Let that sink in for a moment…
At a time when many people still believed disease came from bad air and dancing too closely risked moral collapse, you announced:
“I am beyond gender.”
History occasionally hides lightning bolts inside dusty archives.
Of course, most cross-dressing in Revolutionary America emerged less from identity exploration and more from survival, mobility, or necessity.
Women disguised themselves as men to access worlds closed to them otherwise.
The most famous example would come slightly later with Deborah Sampson, who enlisted in the Continental Army disguised as a man named Robert Shurtliff and fought for over a year before discovery.
Imagine the courage required.
Military camps.
Battlefields.
Shared quarters.
Constant danger of exposure.
Every morning began not merely with war…
but performance.
And she was not alone.
Women occasionally wore male attire for espionage, nighttime travel, message delivery, or economic survival. Riding clothes, coats, hats, and boots allowed movement through spaces otherwise inaccessible to women traveling alone.
Meanwhile enslaved individuals sometimes used clothing strategically to escape bondage. Passing visually as white laborers, sailors, or men could create precious moments of mobility within systems designed to cage human beings permanently.
Clothing became camouflage against oppression.
And that truth matters deeply:
cross-dressing often emerged not from spectacle…
but from constraint.
People crossed gender presentation because rigid societies left them few alternatives.
Still, colonial America remained deeply suspicious of everyday gender nonconformity.
Theatrical cross-dressing existed in masquerades and stage performances inherited from European traditions. Audiences tolerated male actors dressing as women for comedy or performance.
But outside theatrical spaces?
Far less accepted.
The law itself often focused less on gender and more on preserving social hierarchy and public morality. Earlier colonial sumptuary laws attempted to regulate who could wear what based on class and status.
Yet by the late 18th century, gender presentation increasingly became moral territory too.
Public deviation invited scrutiny.
Because societies obsessed with rigid order tend to panic whenever categories blur.
Then came the 19th century.
And cross-dressing spread more widely…
while punishment intensified simultaneously.
America expanded westward.
Cities industrialized.
Opportunities widened unevenly.
For many women, dressing as men became practical route toward:
economic independence,
safer travel,
higher wages,
or participation in male-dominated professions.
On the frontier especially, flexible gender presentation sometimes escaped intense scrutiny simply because survival mattered more than social purity.
A person who could work, ride, shoot, farm, or survive often mattered more than strict conformity in remote environments.
Yet urban America moved sharply toward criminalization.
Starting in the mid-1800s, cities began passing anti-cross-dressing ordinances making it illegal to appear publicly in clothing “not belonging to his or her sex.”
St. Louis pioneered such laws in 1843.
Others followed rapidly:
Chicago,
San Francisco,
New York,
and dozens more.
These “masquerade laws” gave police enormous power to harass anyone challenging gender norms.
And importantly:
the laws rarely targeted wealthy elites equally.
Like many morality laws, enforcement focused disproportionately upon marginalized people:
poor individuals,
queer communities,
sex workers,
immigrants,
and gender-nonconforming people already living precariously.
Clothing became criminal evidence.
Yet paradoxically, cross-dressing flourished simultaneously in entertainment.
Vaudeville stages exploded with male impersonators and female impersonators alike.
Performers like Ella Wesner built successful careers playing with gender presentation theatrically.
Audiences packed theaters enthusiastically to watch gender boundaries blur…
while supporting laws punishing those same boundaries outside performance spaces.
Human beings possess astonishing ability to consume transgression as entertainment while fearing it socially.
Then came the late 19th century’s emerging field of sexology.
And this shifted everything again.
Gender nonconformity increasingly became medicalized.
Doctors, psychiatrists, and early psychologists began categorizing cross-dressing, homosexuality, and gender variance as psychological abnormalities or “inversions.”
What had once been viewed primarily as moral deviance increasingly became framed as pathology.
Which may sound more compassionate initially…
until one realizes medical systems can police people just as aggressively as legal systems.
Then the 20th century arrived.
And cross-dressing entered one of its harshest eras of criminalization.
Anti-cross-dressing laws spread nationwide.
Police enforced rigid gender binaries aggressively through arrests, interrogations, and humiliation.
Many cities informally enforced the infamous “three-article rule,” harassing people if they failed to wear at least three articles of clothing associated with their assigned sex.
Imagine that:
human identity reduced bureaucratically to sock-counting morality.
Police raids targeted queer bars, drag venues, and gender-nonconforming communities routinely.
Newspapers sensationalized arrests.
Mugshots were published publicly.
Lives were destroyed through exposure and shame.
And psychiatric institutions often became extensions of punishment systems. Some gender-nonconforming individuals were institutionalized rather than jailed.
Yet resistance kept growing underground.
Drag flourished secretly in nightlife scenes.
Queer communities built hidden social networks.
Ballroom cultures emerged as sanctuaries for self-expression and survival.
During World Wars I and II, soldiers routinely cross-dressed theatrically in camp performances to entertain troops.
Which means America simultaneously criminalized gender nonconformity publicly…
while cheering it enthusiastically for military morale.
History is wonderfully inconsistent sometimes.
Then came the breaking point.
In 1966, the Compton’s Cafeteria Riot erupted in San Francisco after transgender women and drag queens fought back against police harassment.
Three years later came Stonewall.
And suddenly the culture shifted.
Drag queens,
trans women,
queer youth,
and gender-nonconforming people resisted openly against police violence and legal oppression.
The modern LGBTQ+ rights movement accelerated dramatically from those confrontations.
By the 1970s and beyond, courts increasingly struck down anti-cross-dressing laws as unconstitutional.
The criminal framework slowly weakened.
And now we arrive in 2026.
Where gender expression exists in one of the strangest paradoxes in American history.
Visibility reached unprecedented levels.
Drag became mainstream entertainment partly through RuPaul’s Drag Race, transforming what was once underground nightlife into global pop culture industry.
Fashion itself blurred dramatically.
Men wear skirts, makeup, pearls, crop tops, painted nails, and flowing silhouettes publicly with increasing normalization. Gender-fluid fashion dominates runways, streetwear, celebrity culture, and online aesthetics.
TikTok, Reddit, Instagram, and online communities created global support networks where people experiment safely with presentation, identity, style, and self-expression.
A teenager in rural America can now instantly find thousands of others sharing similar experiences.
That matters profoundly.
And yet…
the political backlash intensified simultaneously.
Across the 2020s, hundreds of bills targeting drag performances, transgender healthcare, public gender expression, and identity protections appeared across state legislatures.
Some framed themselves as “protecting children.”
Others focused on bathroom access, sports participation, or public performance restrictions.
The legal environment became wildly uneven depending on geography.
In one city, drag brunches sell out joyfully beside mimosas and glitter.
A few states away, legislators debate restrictions broad enough to create fear around public gender nonconformity itself.
America currently lives inside competing visions of freedom:
one emphasizing expressive liberty,
another emphasizing traditional social structure.
And beneath all the politics lies something deeply human:
people trying to decide who gets permission to exist comfortably in public.
Public Universal Friend, if you could walk through America in 2026, you would surely marvel at how visible gender experimentation became:
drag performers filling theaters,
celebrities challenging fashion norms,
young people treating identity with remarkable fluidity,
and online communities supporting people across continents instantly.
But We suspect you would also recognize familiar tension beneath the progress.
Because every century struggles with bodies refusing easy categorization.
And every era eventually asks:
Who gets to decide what is “normal”?
Who defines legitimacy?
Who controls presentation itself?
Perhaps that is why your story still resonates.
You did not merely change clothing.
You challenged the assumption that society possessed automatic authority to define your existence for you.
And that remains revolutionary.
With admiration, caution, curiosity, and one aggressively judgmental colonial wig glaring disapprovingly from the corner,
—The Radical Left 👞🖤
And dear reader, perhaps the deeper question after 250 years is this:
Why does clothing provoke such powerful reactions in the first place?
Why do societies become so emotionally invested in who wears what?
Because fabric alone cannot threaten civilization.
But identity can.
Visibility can.
Freedom can.
And perhaps every generation must eventually decide whether individuality represents danger to social order…
or evidence that human beings were never meant to fit perfectly inside rigid categories to begin with.