On Sunday at 11:00 am, January 13, 1929 Police Chief William O'Connell (above) observed two odd looking men at the corner of Barcelona and Romana Streets. Convinced that they were women, he questioned them. When they admitted their sex, he took them to the police station as suspicious characters. They said Thomasville, Georgia was their home and gave their names and ages as Grace Allen, 23, and Dorothy Allen, 20, sisters. They said they had been working in the cigar factory in Thomasville and were on their way to Mobile, Alabama to seek work in a cigar factory there. They started hiking from the Georgia city Friday and said they were wearing the men's clothing because they were easier to walk in and offered protection from other tramps. (Pensacola News Journal 1-24-1929)
Many states including Florida had laws about women dressing in men's clothing during this period of time. My grandmother Carrie Otis Majors told me how she had been forced to dress like a man so she could walk out on the Pensacola Bay railroad trestle to fish. Women were not allowed on the trestle. If caught she said she would have been arrested for violating the law." Many of these laws during this period of time were associated with prostitution whereas a woman's clothing may suggest something sexual in nature.
Chief William J. O'Connell, 1885-1947, Buried in St. Michaels' Cemetery. Chief of Police Pensacola 1927-1947.
Pensacola News Journal 1-14-1929