This previous thread discussing how gay bars in New York were predominantly run by the mafia has the following section:
In San Francisco, Sal Stoueman's Black Cat Cafe (made particularly famous by Jack Kerouac and Allen Ginsberg) handed out "I'm A Boy" nametags to patrons, so undercover cops could not arrest its drag performers, "gay screaming queens" (TM Ginsberg), or even "gray flannel suit types" for female impersonation with intent to defraud or deceive someone into sex.
In the present day, GLADD's website condemns the notion of "trapping someone" as defamatory to transgender individuals, stating:
Gender identity is an integral part of a person's identity. Do not characterize transgender people as "deceptive," as "fooling" or "trapping" others, or as "pretending" to be, "posing" or "masquerading" as a man or a woman. Such descriptions are inaccurate, defamatory and insulting. (See "passing" and "stealth" as problematic terms above.)
This particular form of pejorative language appears to have originated in its application to transgender and transvestite individuals in the early 1990's if not earlier.
Is there any direct, causal link between the laws prohibiting female impersonation in the 1960's and the defamatory language directed toward transvestite and transgender men in the 1980's and 1990's?
In addition, are there any activists that addressed this issue of sexual entrapment directly in ways similar to the Black Cat Cafe in the mid-to-late 20th century?
(Note: By nature this post deals with police harassment toward people we would now call LGBTQ, as well as homophobic/transphobic violence.)
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Incidents like Stoueman's name tags were pretty atypical in the history of gay bar ownership and female impersonation in the 1950s and 1960s, but this points toward something pretty significant about the LGBTQ experience in these decades. Legal statutes prohibiting crossdressing were common across the United States well through the 1970s -- many of these statutes were a product of the second half of the 19th century, and were interpreted broadly almost a century later to roust drag queens appearing in private venues, gay and bisexual people meeting in public, crossdressers, and what we would now call transgender individuals, regardless of whether the people being rousted for crossdressing could be reasonably described as attempting to trick anyone, sexually or otherwise, or even as attempting to present themselves compellingly as something they were not. Such statutes could be applied even when other methods of entrapment were unsuccessful, or if no other "disorderly" acts had taken place -- often they served as a pretense for raids on establishments where gay men and lesbians gathered amongst themselves, and where no truly unwitting heterosexual was likely to spend much time.
The enforcement of these statutes was degrading. Busts on gay bars and gathering-places were an occasion for police brutality, and detained individuals might be verbally harassed and forced to strip, or to have their genitals examined by police officers. Standards for attire were often employed indiscriminately, with police officers rounding up individuals who could be described as only partially crossdressed. The conceit that gender impersonation was a sort of disguise was an (im)polite fiction used by law enforcement even if an individual was involved in nothing nefarious enough to warrant a disguise, or an individual's secondary sex characteristics were highly visible and they openly acknowledged that they were crossdressing to everyone present, or if an individual's other attire was otherwise typical of what was expected of them and a genuine misunderstanding was unlikely.
In Queer Law and Order: Sex, Criminality, and Policing in the Late Twentieth-Century United States Timothy Stewart-Winter writes,
In a February 1961 raid on the C&C Club, a blue-collar lesbian bar in Chicago, more than fifty women were arrested along with the bartender. At the police station, “those women wearing ‘fly fronts,’ regardless of whether they wore lipstick, long hair, or earrings, were made partially to undress in order to determine whether they wore jockey shorts,” according to one account.
Laws regarding crossdressing varied by city and state, though almost every community had some form of codified standard for appropriate and inappropriate dress. Some city and state statutes explicitly mentioned attire specific to gender and sex; other statutes referred more broadly to "disguise" or "unlawful purposes", and the enforcement of these statutes adapted accordingly. Just the same, so did individual practices. Maneuvers like the Black Cat Club's name tags were not commonly adopted across the United States; there were other defensive maneuvers adopted by individuals whose dress made them a target for police interference. Individuals might avoid certain venues, meet in private homes, or wear a mix of gendered clothing in order to skirt a real or perceived legal technicality. In midcentury New York, the informal threshold between a non-crossdressed individual and a crossdressed individual who was then in violation of the law was commonly understood to be three (sometimes two) articles of clothing belonging to the "correct" gender -- this was not enshrined in law at a state level, but was applied to both male and female impersonators. In Boots of Leather, Slippers of Gold, Elizabeth Lapovsky Kennedy and Madeline D. Davis write:
We have not been able to find a New York State law about what constitutes male or female impersonation, despite the unanimity of narrators on the subject. [...] An 1845 vagrancy law defines a vagrant as a person who disguises herself in order to prevent identification. This law was adopted in response to antirent demonstrations by farmers who masqueraded as Indians and served as the basis for criminalizing cross-dressing until 1967. After 1967 the police prosecuted cross-dressing under the loitering law which prohibits disguise in public places. In 1974 the courts found such prosecution outside of the intent of the loitering law and all arrests on cross-dressing have ceased in New York State. See Nan Hunter, “Gender Disguise and the Law,” unpublished paper presented at the Eighth Berkshire Conference on the History of Women, Douglass College at Rutgers University, June 1990.
This footnote comes after a passage wherein a butch woman describes being harassed by police officers in Buffalo, NY for being seen wearing a men's shirt and trousers:
"I’ve had the police walk up to me and say, ‘Get out of the car’. I’m drivin.’ They say get out of the car; and I get out. And they say, ‘What kind of shoes you got on? You got on men’s shoes?’ And I say, ‘No, I got on women’s shoes.’ I got on some basket-weave women’s shoes. And he say, ‘Well you damn lucky.’’Cause everything else I had on were men’s—shirts, pants. At that time when they pick you up, if you didn’t have two garments that belong to a woman you could go to jail… and the same thing with a man.… They call it male impersonation or female impersonation and they’d take you downtown. It would really just be an inconvenience. … It would give them the opportunity to whack the shit out of you.”
There is indeed no mention of "three articles of clothing" in the vagrancy statutes of New York state or anywhere else I could find, but this figure recurs in midcentury American LGBTQ writings as a guideline for the evasion of criminal charges even outside the New York area. Another woman, Reba Hudson, said of San Francisco, CA in the 1950s:
"They were plainclothesmen that were out to hassle gay bar owners, and we just happened to be in there. They’d conduct little raids, right? And now we know that the bar owners that were running gay bars that weren’t bothered were paying off the cops. We fell into the vice squad category, right along with the whores and the pimps and other vice squad victims. But that’s the only time that I was ever actually personally harassed. Others got harassed more often, like the dykes that dressed up in men’s clothing. But they always wore women’s underpants, because if you wore one article of feminine apparel—the same thing was true of drag queens—they couldn’t book you for impersonating a person of the opposite sex. I think that was the way they phrased it. Seems incredible now."
(So the "x items of clothing and you can't get in trouble" thing seems to have been a piece of gay lore, almost, rather than a reflection of a legally mandated reality.)