A pirate should dress on how they want to be know as. If they are want to be a dashing and flashing pirate, and bright clothes should do. If they want to be feared, darker colors should be worn (ex. Barbossa outfit.)
A pirate should also dress if they want to show off their rank. A captain should wear elaborate clothing to show off their riches and spoils. A first mate or boatswain should wear elaborate clothing as well but not as much as the captain if they don't want to risk offending him or her. Any other pirates in the crew should try to look as fearsome as possible to intimidate other enemies.
A pirate should also dress to repersent there fighting skill. A swordsman, such as myself, should where long coats and large hats. Despite the Caribbean heat, no trace of skin should be seen besides the hands and face. This is useful for concealing swords and sabres.
Gunners and pistol users can where anything that doesn't interfer with loading and firing guns. A signature symbol of an gunpowder worker is a bandana, used for keeping the loud sounds of gunfire from deafening one's ear.
Voodoo practinoers should expose their chests, revealing an exotic tattoo. Wearing as much tattoos as possible will sharpen the image of a terrifying voodun magican.
Long hair is admire but baldness or mohawks give off a auroa of toughness. Beards are good for intimidation as well and a simple mustache shows off a charming side to any rouge.
Follow these rules well but remember they are more like guidlines...
Do you have any rules to add?