The thing you have to remember is that most pirate Captains were not captains before they joined pirate crews. Some would have been officers in the Royal or Merchant Navy, others might have been a part of privateer ships and worked their way up to the rank of pirate Captain. A few may have simply mutinied and become Captain this way.
How did pirates captains dress?
It’s very likely that a Pirate Captain would dress much like their crew which was, of course, according to the times. Especially on pirate vessels, where Captains shared the heavy work with their men, this would mean practical seafarers clothes.
Despite the impracticability of finery, some pirate Captains were known to take great pleasure in dressing themselves in the latests fashion, particularly when they were celebrating ashore. In such circumstances their clothes would have been influenced, most likely, by the military or naval fashion of the day. Instead of canvas or wool, however, you can be sure you would have seen some silks, brocades and damasks. It is doubtful that these clothes would have been worn at sea, but certainly the clothes worn at sea would have been practical adaptations of the fashions on shore. This mean that tarred canvas coats would have been worn rather than heavy wool, and light linen might have been favoured over silk by pirate captains, especially in the Caribbean.
There has been some evidence to show that this adaptation of fashion was, indeed, a reality. When long coats with large cuffs were fashionable in the 1680s, for example, shades of this could be seen on board naval and pirate ships. This is shown by pictures of officers wearing long coats with a more practical mariner’s cuff rather than the long ones.
One interesting thing that was reported about pirate Captains and their dress codes; upon capture by Naval forces they would alter their clothes in order to blend in with the rest of the crew, especially if they were in danger of being captured. The pirate captain would want to pass of as a member of the crew.