Pirate John Rackham, famously know as "Calico Jack," is most remembered for his female crew members and his outlandish clothing, rather than his exploits as a pirate.
Rackham took on the nickname "Calico" for opting to wear cotton clothes instead of the more common silks and velvets in fashion at the time. His career as a pirate began when he was elected captain of a ship in 1718. The choice to fire on a French ship, against the wishes of the original Captain, Charles Vane, is what landed Calico Jack the job, and resulted in the crew dismissing Capt. Vane. Now considered a pirate, he sailed the Caribbean for several months, attacking smaller ships and taking their treasures. Calico Jack is also known for coming up with his own version of the Jolly Roger flag, with a skull and two crossed swords instead of two crossed bones.
Calico Jack soon settled down in New Providence in 1719. He was granted a pardon by Woodes Rogers, and soon after began an affair with a married woman, Anne Bonny. In order to be with Bonny, he ignored the pardon and took to the sea again, this time stealing a vessel known as the Curlew. He took his lover onboard with him, along with her husband James Bonny. While James worked as part of the crew, Anne dressed like a man to blend in with the pirates. Since James was mostly concerned with receiving part of the pirate's treasure, he looked the other way when his wife and Rackham had a child. Eventually they left the child in the care of pirates living in Cuba, so Anne could continue to ride with the pirate ship.
This odd arrangement lasted for over a year while they attacked smaller vessels along the West Indies. Calico Jack took on a new sailor whom he felt was spending too much time around Anne. He soon found out that this new sailor was a woman, named Mary Read, who was integral part of Calico Jack's crew. Near the end of October 1720, a British Navy ship led by Captain Barnet went after Calico Jack and his crew. They caught up with the pirate ship in the Jamaican waters. The crew were reportedly so drunk under deck that the two women were left to defend the ship alone. Soon the women were overtaken and the ship was captured. The entire crew were arrested and taken to Jamaica for trial. Both women were pregnant, so they escaped hanging, but Calico Jack and the rest of his crew were hung on November 27, 1720.