What does a pirate look like?

How should you dress if you want to represent a pirate? This is a conundrum. The contemporary pictures were not drawn by eyewitnesses. At best, they represent how a contemporary person interpreted the descriptions of others.

There are a few eyewitness accounts. From that, the average pirate dressed like an average sailor. That means either long pants or slops and a short jacket.

The problem is that, if you dress like an 18th century sailor, most people are not going to know that you are portraying a pirate.

There are some things that you can do to liven up an impression. Sailors in general and pirates specifically would have access to some exotic accessories and some affected an unusual appearance.

Gold earings and a silk skarf or bandanna can certainly be justified.

Captains dressed better than crewmen, often dressing like a navy officer. They were more likely to add extra touches. Blackbeard is the ultimate example with a long, bushy black beard that he tied up with ribbons.

Pirates fought more often than regular sailors, probably more often than seamen in the navy. They walked around heavily armed. There are several descriptions of pirates wearing a sash with a brace (pair) of pistols tucked in it. They often wore a sword on a baldric.

Pirates often went into battle with a badric holding up to six holstered pistols. This was important in hand-to-hand combat. It takes several seconds and both hands to load a pistol and you only get one shot (or none if the powder is wet). The only way to get multiple shots was to carry multiple pistols.

I'm not sure about justification for bucket topped boots. At sea, pirates tended to go barefoot to avoid slipping. On shore, at port, they might dress up.

The tricorn (a three-cornered hat) was pretty universal from the late 17th century through the early 19th century. It is not something that a pirate would wear at sea - it is too easily knocked off while climbing the rigging or simply blown off, but it is something else that a pirate might wear at port to dress up.

The parrot as an accessory comes from Treasure Island. Long John Silver kept one. They are common in the Caribbean and were in demand elsewhere. Some pirates were known to give parrots as gifts. There is no reason why a pirate could not pick up a parrot as a pet or something to be sold later.