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, 19yrs 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 outlawed cross-dressing as early as 1851.