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History: Who wears the pants?
Special to the Online Edition of Windy City Times
by John D'Emilio

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Many of my students joke about the "gender police."

Of course, they're not talking about an actual division of the Chicago Police Department or any other law enforcement agency. Instead, they're referring to all those arbiters of behavior who force people into the straightjacket of appropriate male and female behavior. The list of culprits is long: the popular boys and girls in high school: advertisers and Hollywood celebrities; school principals and sports coaches; and many others.

What they often don't realize is that, for most of Chicago's history, policing gender did actually fall to the police. Chicago passed its first law against cross-dressing in 1851, when it was still not much more than a frontier town. The prohibition against cross-dressing was included in a broader statute that made it a crime if anyone "shall appear in a 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, or shall make an indecent exposure of his or her person, or be guilty of an indecent or lewd act."

Chicago was not alone in passing such a law. According to Bill Eskridge, author of Gaylaw, in the second half of the 19th century "cities of every size and in every part of the country" adopted laws to enforce gender-conforming dress codes.

These laws remained on the books for over a century. Then, in the 1970s, most of them bit the dust. The challenges to enforcing gender-based clothing norms became overwhelming. Male hippies were growing their hair to shoulder length. Women's liberationists were violating all sorts of gender boundaries. High school students were refusing to abide by the dress codes set by adults and were going to court to protect their right to self-expression. Even straight-as-an-arrow business executives were abandoning the male costume of suit jacket, hat and tie.

But Chicago found itself in an uproar about its cross-dressing ban a whole generation earlier. In the middle of World War II, an independent-minded 19-year-old provoked front-page news stories, judicial sermons, outraged comments from government officials, and debates among the city's alderman. When it was all over, the city's cross-dressing law had been revised in an important way.

It all began on a January night in 1943 when Evelyn "Jackie" Bross was picked up by the Chicago police. Bross was the eldest of 13 children in a Cherokee family. Her father had moved them to Chicago from Utah in order to take advantage of wartime job opportunities. Like her father, Bross worked in a defense plant and was employed as a machinist. She worked at the Chicago Die Casting Company at 2512 W. Monroe, and was walking to her home at 2754 W. Jackson when the police stopped her. According to the Tribune, Bross was "dressed in blue flannel trousers, a plaid sport shirt, a plaid mackinaw jacket and oxfords." Topping it off, she had "a mannish hair cut."

Appearing in Women's Court the next morning, Bross told Judge Jacob Braude that she wore men's clothes because they "were more comfortable than women's clothes and handy for work." She stood her ground defiantly. "I wish I was a boy," she declared. "I never did any wrong. I just like to wear men's clothes." Denying that she was trying to deceive anyone, she informed the court that "everyone knows I'm a woman." Judge Braude avoided an immediate decision by ordering Bross to see a court psychiatrist.

Coming in the middle of wartime, when millions of women were wearing pants every day in shipyards and aircraft factories and other defense jobs, the arrest of Bross hit a raw nerve. Many spoke out on her behalf. The city's leading club women supported her on feminist grounds: "Women's suffrage and slacks ought to go hand in hand," the Tribune reported them arguing. Harry Guilbert, head of the regional federal office for war-industry employment, was enraged at the arrest. "If the girl cut her hair short, she should be awarded a medal instead of a court summons," he told reporters. "Safety directors in factories everywhere have tried to encourage women to cut their hair short."

The arrest of Bross provoked action by the board of aldermen. William Cowhey of the 41st Ward spoke up at a board meeting the day after Bross was arrested. He proposed an amendment to the law in order to prohibit cross-dressing only when there was "intent to conceal his or her sex."

One can just imagine the snickers in the aldermanic chambers that day. Members were debating the city's budget in the midst of a war, and here was Cowhey asking them to take a stand on who could wear pants. But, the aldermen also didn't anticipate the level of public interest. Cowhey wrapped his proposal in wartime patriotism. "We're in a war," he told the aldermen. "Today, with the war industries calling for safe dress, we should permit women to wear comfortable clothes. If slacks are comfortable, let them be worn!"

Cowhey's proposal passed. The statute against cross-dressing was amended. Now it was supposedly okay in Chicago to wear whatever clothes you wanted—as long as police couldn't claim you were trying to deceive others or that the clothing was lewd. Milking the debate for a few laughs, the front page story in the Daily News informed readers that it was now "perfectly permissible for housekeeping husbands to wear the kitchen apron out for a dash to the grocery."

But the debate about who could wear pants didn't end with law reform. Judge Braude decided to exercise some judicial discretion and used the bench as a pulpit.

The next week, when Bross returned to court, a strange drama unfolded. Also in the Women's Court that day was Theodora Fitzpatrick. No one would mistake her for a man. The papers described her as looking "a bit like a Hollywood star." With a "mass of wavy blond hair, tied with a blue ribbon," she wore "a neat tailored slacks suit." The police had picked her up on suspicion of prostitution. In fact, she was returning from a visit to New York to see her sailor husband.

The contrast with Bross couldn't have been greater. Braude made them stand side by side, the glamorous blonde and the factory worker in "rough trousers, sweater, lumberjack shirt, and muffler."

The judge could not resist sermonizing. "Miss Fitzpatrick has a right to wear slacks," he said. "Miss Fitzpatrick shows that there should be no objection to women wearing slacks if the wearer does not intend to impersonate a male." Looking sternly at Bross, he pointedly said "there's a difference."

Given the public outrage over the arrest of Evelyn Bross, Braude was not about to find her guilty and send her to jail. But he just wouldn't let go of his gender policing role, and he put Bross under psychiatric supervision for six months.

Bross didn't give an inch. Defiant to the end, Bross told the judge directly: "I'll put on a skirt if I have to, but I won't let my hair grow. If I dress like a girl, I'll look like a boy anyway, and I'll be picked up more often—the police will say I'm impersonating a girl."

As a historian, there's so much more about this episode that I want to know. What happened to Evelyn Bross in the succeeding decades? Did Bross stay in Chicago, or return to Utah after the war? If Bross stayed, did she make a life for herself in the circles of butch-fem lesbians who patronized the bars of the 1950s and 1960s? Or did Bross, as some of the press quotes suggest, see himself as male so that today, perhaps, he might have identified as trans?

And what about Bross's Cherokee heritage? The news articles suggest that the family accepted Bross for who she—or he—was. Does this offer some insight into the traditions of many native American peoples who made space in their cultures for gender crossing individuals? The newspaper articles that I stumbled across don't give me enough information to know.

But one thing I can say for sure. Despite the public support for Evelyn Bross and the change in Chicago's cross-dressing law, in the postwar decades the police kept making arrests—at lesbian and gay bars and on the streets of Chicago—of those who pushed against gender norms in clothing. "Who wears the pants" remained a hot topic for another generation.

Copyright 2009 John D'Emilio

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