Real pirates wore whatever they wanted, including the clothing they captured from other ships or port facilities. While many wore ordinary seaman's garb, it was not unusual for a pirate to wear velvets and silk captured from ships carrying luggage owned by wealthy people, and many pirates even wore ladies' garments.
Most pirates had been regular seamen before, so slops, standard military-issue sailor garments, were common work attire. Slops consisted of a woolen Monmouth cap, a canvas doublet, cotton pants, and linen shirts and undergarments; these clothes were practical work attire for daily life on a ship. Shoes were optional on ship, and it was often safer to go barefoot for tasks such as climbing rigging.
For captains or for ordinary pirates on shore, rules changed completely. Sumptuary laws restricted ordinary lower-class people from wearing many fabrics, including lace, silk, velvet, and brocades. Pirates, true rebels, loved flouting these laws, so they wore anything they had on hand that was rich and brightly colored. Some pirates became known for their unusual dress. Calico Jack Rackham, for instance, preferred bright calico prints for his pants and shirts. In addition, pirates often wore jewelry of all sorts they captured from their victims. Most pirates also wore at least a single gold ring in one ear, either for luck or to have at least one valuable item on their persons no matter what happened. A wide sash around the waist for holding extra weapons generally completed the pirate ensemble.