Mary Read

Mary Read was born in London and was the child of an affair like her friend and fellow pirate Anne Bonny. Mary's mother hid the news from relatives, dressed Mary up as the boy, and so continued to receive money that was given for the son's upbringing.
After tiring of serving as a footboy to a wealthy French woman, she spent time as a cabin boy on a warship before eventually fighting as a dragoon, where she met her future husband during the War of Spanish Succession....
Read more at The Pirate's Realm.

'Calico' Jack Rackham

"Calico" Jack Rackham is remembered more for his favorite clothing and his female crewmembers than for his mediocre accomplishments as a pirate. His nickname is for the cheap and brightly colored cotton clothes he was fond of.
One of the first references to him finds him as quartermaster for Charles Vane's operation out of New Providence, Bahamas in 1718. Late that year, Vane fired on a French vessel that he then discovered was a warship. Although he felt discretion and retreat was the better part of valor, his crew disagreed, and the next day he was sent off after Rackham was elected captain.
Read more at The Pirate's Realm.