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Evelyn “Jackie” Bross and Catherine Barscz at the Racine Ave police station, 1943, Chicago.

From the Chicago History Museum:

Evelyn “Jackie” Bross (left) and Catherine Barscz (right) at the Racine Avenue Police Station, Chicago, June 5, 1943

In 1943 Evelyn “Jackie” Bross of Cherokee heritage, was arrested on her way home from work for violating Chicago’s cross-dressing and public indecency ordinance. Bross, who was 19 at the time, and a machinist at a WWII defense plant, wore men’s clothes and sported a man’s hair cut – that was more than enough for the Chicago police. Chicago possessed an ordinance outlawing cross-dressing as early as 1851.

For the bulk of the city’s history cross-dressing was a type of indecent exposure.  The ordinance decrees that “If any person shall appear in a public place…in a dress not belonging to his or her sex…. He or she shall be subject to a fine of not less than twenty dollars nor more than one hundred dollars for each offense”.

When Bross appeared in court, Chicago was captivated by the story. In court, Bross reportedly informed the judge that she chose to wear men’s clothing because it was “more comfortable than women’s clothes and handy for work.” She openly declared, “I wish I was a boy. I never did anything wrong. I just like to wear men’s clothes… [but] everyone knows I’m a woman.”

In the end, Bross was ordered to see a court psychiatrist for six months and Chicago’s cross-dressing code was revised. As of 1943, the code allowed for individuals to wear clothing of the opposite sex, provided it was not worn “with the intent to conceal his or her sex.” Arrests continued in spite of the alteration and the Chicago code regarding cross-dressing would not be eliminated until 1978.