Many pirate captains had not been captains before they became pirates. Some had been officers on merchant, privateer or naval ships, some worked their way up through the ranks of the pirates to achieve command, some led mutinies and became pirates that way. However they became a captain though it is likely that many pirate leaders dressed in a very similar fashion to their men, according to the time they lived in. On small pirate vessels particularly the captain still had to do his fair share of work so would be more likely to dress in practical seamen’s clothing than fashionable finery.
On the other hand, some captains we know took great pleasure in dressing themselves as richly as they could, particularly when celebrating ashore. Their clothes in these circumstances would have been influenced by the naval or military fashion of the day, which in turn was influenced by the prevalent civilian fashions. Instead of canvas and wool their clothes were made of silks, brocades, damasks and calicoes.
Whether they often wore these fine clothes at sea is doubtful. Far more likely they wore clothes similar to the prevailing fashions, but cut from cloth more suitable life aboard ship. Tarred canvas coats perhaps covered brocade waistcoats, light linen breeches were perhaps considered more practical in the Caribbean than silk. Similarly there is evidence to show that some sea officers adapted fashionable clothing styles for use at sea. In the 1680s for example, when long coats with large cuffs were fashionable, we see pictures of officers wearing long coats but with the cuffs removed and replaced by the more practical mariner’s cuff. A portrait of Admiral Leake from a little later shows a mariner’s cuff incorporated into the fashionable turn-back cuff of the time.