How to Fight a Cross-Dressing Charge
It helped to say you were a preoperative transsexual
Did cross-dressing bans hurt people who identified as the opposite sex? Well, sure. But they targeted other misfits, too. And in the 1970s, judges in some states exempted “transsexuals” from them even if they hadn’t medicalized.
In this post I’ll cover the major quaalude-era court cases on impersonating the opposite sex. I’ll also sketch the broader history of the statute that New York City cops (NYPD) used to arrest gay and gender-nonconforming people, so you can see what we miss when we view everything through a gender lens.
The Vagrancy Statute (New York, 1845)
The nation’s most notorious cross-dressing law said nothing about sex or gender. Passed by the New York state legislature in 1845, it was, in the words of a 2004 federal appellate court, “indisputably aimed at deterring violence and facilitating the apprehension of wrongdoers[.]”
In the years leading up to the law’s passage, wealthy landowners in the Hudson Valley – a bucolic region between the Bronx and Albany – were squeezing the farmers who worked their land. Citing two historians, the 2004 court described the scene:
“Their livelihood threatened, tenants organized anti-rent associations to muster funds for litigation and to exert pressure on legislators. Some anti-renters formed bands of so-called ‘Indians,’ disguised in calico gowns and leather masks, who forcibly thwarted landlords' efforts to serve farmers with process or to conduct distress sales. The operations of the masked Indians commonly involved intimidation, and sometimes tarring and feathering, but also caused three deaths from 1844-45, including the death of a sheriff.”
The vagrancy statute authorized the pursuit and arrest of any person who "having his face painted, discolored, covered or concealed, or being otherwise disguised, in a manner calculated to prevent him from being identified, shall appear in any road or public highway, or in any field, lot, wood or enclosure."
The sociologist Clare Sears, writing for Jacobin in 2023, described the lead up to the law’s passage differently. Sears claimed it was enacted “in response to rural workers who wore women’s dresses and masks while participating in anti-rent protests.”
I’m not a real historian, just a Substack historian – worse, a legal historian – so I can’t determine which account best captures the truth of the matter. Were the state reps of 1845 concerned about violent rebels disguised as Indians or did they fear gender-fluid peasants waving signs? I don’t know; I can only point out that Sears prefers they/them pronouns.
People v. Archibald (NYC, 1968)
Over time New York’s vagrancy law was turned against cross-dressers. In 1913 cops arrested a woman for “masquerading in men’s clothes.” The magistrate tossed the case because the law was only meant to criminalize costumes used as cover for another crime. The cops tried again, and a different magistrate convicted her because “No girl would dress in men’s clothing unless she is twisted in her moral viewpoint[.]”
Arrests of cross-dressers ramped up in mid-century New York City as cops used the vagrancy law to hassle gender-nonconforming people and patrons of gay bars. In 1968, a state appellate court considered People v. Archibald:
“[W]hile patrolling a subway station platform at 4:00 A.M., [the police officer] observed three people engaged in a loud conversation. The officer testified that after he passed the group, ‘the defendant turned around and over the right shoulder winked at me with his eye and again turned around and continued walking away from me’ … The officer spoke briefly to the defendant and when asked whether he was a boy or girl, the defendant replied ‘I am a girl’. … the defendant was wearing a white evening dress, high heel shoes, blonde wig, female undergarments, and facial makeup.”
The panel of judges upheld the defendant’s conviction as a vagrant. He’d argued that the law was unconstitutionally vague, but the panel rejected that without discussion.
A dissenting judge, however, took a more cosmopolitan view:
“If appellant's conviction was correct then circus clowns, strangely attired ‘hippies', flowing-haired ‘yippies' and every person who would indulge in the Halloween tradition of ‘Trick or Treat’ ipso facto may be targets for criminal sanctions as vagrants. … a young man or woman could possibly be convicted … as a vagrant merely for venturing into the street in his or her normal attire, which is otherwise acceptable in society today.”
Soon after Archibald, the 1969 Stonewall uprising in Manhattan’s West Village quelled NYPD’s targeting of gays and cross-dressers.
And New York tweaked the statute. Vagrancy was out, replaced with “loitering.” A loiterer was someone who, while “masked or in any manner disguised by unusual or unnatural attire or facial alteration, loiters, remains or congregates in a public place with other persons so masked or disguised.”
Other Cities
Outside New York, laws that cops used against cross-dressers tended to be city ordinances enacted in the mid-1800s. These laws explicitly banned impersonating the opposite sex. Some were ostensibly aimed at thwarting tricksters and fugitives, but they smacked of Victorian moralism and were used to hassle gender-nonconforming people in the mid-20th century.
City of Columbus v. Zanders (Ohio, 1970)
Columbus, Ohio’s ordinance read:
“No person shall appear upon any public street or other public place in a state of nudity or in a dress not belonging to his or her sex, or in an indecent or lewd dress.”
In City of Columbus v. Zanders (1970), a trial court judge quoted the sexologist Harry Benjamin for eight paragraphs about the nature of transsexuality before concluding that the cross-dressing male defendant’s desire to be a woman constituted a “mental defect” – in other words, the judge acquitted him by reason of insanity.
City of Columbus v. Rogers (Ohio, 1975)
A few years later a challenge to the same statute made it to Ohio’s highest court. In City of Columbus v. Rogers, these judges picked up where the Archibald dissent left off:
“Modes of dress for both men and women are historically subject to changes in fashion. At the present time, clothing is sold for both sexes which is so similar in appearance that ‘a person of ordinary intelligence’ might not be able to identify it as male or female dress.”
The court struck down the cross-dressing ban on the grounds that it was unconstitutionally vague. Cross-dressers who lived or partied in Columbus could thank the fashion industry for selling clothing that perplexed judges.
City of Chicago v. Wilson (Chicago, 1978)
In City of Chicago v. Wilson, Illinois’ highest court considered a Chicago ordinance that, in the words of the judges, “prohibits a person from wearing clothing of the opposite sex with the intent to conceal his or her sex.”
The court described the alleged offense:
“Defendants were arrested on February 18, 1974, minutes after they emerged from a restaurant where they had had breakfast. Defendant Wilson was wearing a black knee-length dress, a fur coat, nylon stockings and a black wig. Defendant Kimberley had a bouffant hair style and was wearing a pants suit, high-heeled shoes and cosmetic makeup. Defendants were taken to the police station and were required to pose for pictures in various stages of undress. Both defendants were wearing brassieres and garter belts; both had male genitals.”
The City of Chicago defended its ban. The court recapped its arguments:
“[T]he city has asserted four reasons for the total ban against cross-dressing in public: (1) to protect citizens from being misled or defrauded; (2) to aid in the description and detection of criminals; (3) to prevent crimes in washrooms; and (4) to prevent inherently antisocial conduct which is contrary to the accepted norms of our society.”
Finding those arguments unsupported by evidence, the court turned to the defendants’ contention that they were transsexuals getting ready for genital surgery, and their doctors had required them to “wear female clothing and to adopt a female life-style.”
Citing a 1976 US Supreme Court decision about police uniforms, the Illinois court applied a balancing test: “the degree of protection to be accorded an individual's choice of appearance is dependent upon the context in which the right is asserted.” Considering the defendants, the court declared:
“[W]e cannot assume that individuals who cross-dress for purposes of therapy are prone to commit crimes. … There is no evidence … that cross-dressing, when done as a part of a preoperative therapy program or otherwise, is, in and of itself, harmful to society. In this case, the aesthetic preference of society must be balanced against the individual's well-being. … It would be inconsistent to permit sex-reassignment surgery yet, at the same time, impede the necessary therapy in preparation for such surgery.”
The court overturned the convictions on the grounds that they violated the defendants’ constitutional “liberty interests” – a theory known as substantive due process that protects important rights that aren’t spelled out in the Constitution, like the right to have consensual sex.
The judges let Chicago’s cross-dressing law stand so it could be used against other gender criminals who weren’t slated for castration.
The defendants’ claim to be prepping for genital surgery seemed like a ruse, according to a dissent joined by three judges. There was no evidence for it except their own sketchy testimony. Defendant Wilson, for example, “didn't know what sex-reassignment surgery would involve and said he did not know the doctor who would perform it.”
This is the earliest case I’ve encountered in which the ACLU represented a trans client (though it was reportedly involved in the matter of Paula Grossman, the elementary school teacher). I imagine the ACLU was eager to argue that the cross-dressing ban violated the First Amendment right to free expression – a point that the defendants made and the court dodged.
Doe v. McConn (Houston, 1980)
In 1980 a federal court in Texas applied the same reasoning to a similar ordinance in Doe v. McConn. Citing Wilson and Roe v. Wade, among others related to “liberty interests,” the court found that Houston’s ordinance was unconstitutional “as applied to individuals undergoing psychiatric therapy in preparation for sex-reassignment surgery[.]”
The judge rambled for 15 paragraphs about the diagnosis, etiology, and treatment of transsexuality, without citing a single source. Despite this remarkable lack of rigor, in 2019 a federal court in California cited McConn as authority for the idea that “gender identity is biologically determined.” (Gender identity is not biologically determined.)
The Demise of Cross-Dressing Bans
After McConn, the cross-dressing courtroom trail goes cold. I guess local officials stopped enforcing their bans by the 1980s; maybe some cities repealed them. If the ordinances landed in court today, they’d be struck down for violating the constitutional right to free expression (and other rights). As to recent restrictions on drag shows – we’ll get there when we get there!
Back in New York, a Brooklyn criminal court judge in 1974 found, through an elaborate analysis, that the state’s law on impersonation didn’t ban cross-dressing (“the human species is the only one in which true gender can be more or less successfully concealed”). That was the last gasp of gender prudery in the big apple.
But the loitering law powered through the decades as a cudgel against protestors. In 2004, the NYPD denied the Ku Klux Klan a permit to rally in lower Manhattan because the klansmen planned to disguise their faces. The ACLU’s New York affiliate, the NYCLU, represented the KKK in challenging the permit denial, arguing that the mask ban violated the KKK’s right to free expression. The federal Second Circuit of Appeals upheld the law, reasoning that KKK members could fully express themselves using robes and hats. The panel included future US Supreme Court justice Sonia Sotomayor.
In 2011, NYPD arrested Occupy Wall Street protestors for wearing Guy Fawkes masks. In 2012, NYPD arrested Pussy Riot supporters for rallying in balaclavas outside the Russian Consulate. The defendants retained a former NYCLU bigwig to defend them and challenge the law – but prosecutors dropped the charges before they got their chance.
Progressives took over New York’s legislature in 2019 and moved to repeal the loitering statute. By the time it came up for debate, in May 2020, ambulance sirens were blaring almost continuously in Brooklyn. New York’s governor had suspended the 1845 mask ban by executive order. In Albany, masked democratic legislators spoke for repeal while unmasked republicans fretted about the prospect of hate groups and criminals marauding anonymously. The media outlet City and State chronicled the pattern:
“Not only were many Republican lawmakers opposed to the measure – they expressed their opinions with barefaced appearances on a video livestream … To be fair to GOP lawmakers, Assembly Democrats were also going maskless at times during the session on Wednesday, including Assemblyman Jeffrion Aubry, who proceeds over the chamber with a booming voice that likely projects droplets all over the place.”
Clothing is about so much more than gender.
This post was lightly edited on Sept. 28, 2024.