Anne Bonny was an infamous pirate who lived during the beginning of the 18th century. Born in Ireland as the result of an illicit affair, she moved to the Bahamas with her father when she was young. There, she developed a love of adventure and rebellion. She defied the status quo for young ladies by drinking, playing with a sword, and general swashbuckling late into the night at local watering holes. Anne grew a reputation for having a fierce temper and being the lover of notoriously feared (and flamboyantly dressed) pirate Calico Jack. At his side, Anne quickly rose through the ranks to become one of the most feared pirates in the Caribbean.

Anne dressed as a man on board, but revealed her true identity to a shipmate that she developed feelings for, only for him to reveal that he was also a woman dressed as a man. Thus created the dynamic duo of legend, Anne Bonny and Mary Read. The two of them were eventually captured, but only after holding off British forces long after every one of their male shipmates had forfeited. Anne and Mary were spared the death penalty because, even while slinging swords and hauling masts, both women were pregnant. After this the two disappeared into history.... and they were roommates ;)

Check out the dress Anne inspired here.