Fascinating True Stories From the Flip Side of History

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Dressed Like a Man for Halloween

Back in 1921, New York City resident, Etta Caulfield decided to dress up as a man for Halloween. She borrowed her brother’s shirt, tall-stiff detachable collar, pants, and an overcoat to complete the costume.  

As she set out along Broadway en route to a Halloween Party, men started to follow her and a crowd soon gathered. Shortly after that, a patrolman was summoned and he arrested Ms. Caulfield on the spot. It’s unclear what the charges were, but she was released the next day after spending a night under the supervision of a police matron.

Halloween Card from 1910

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