Pirate

What most people think of as a pirate - tricorne hat or bandanna, wooden leg, gold dubloons, skull and crossbones flag, rum, etc, didn't exist until at least the 17th century. However raiders or pirates certainly plied their trade earlier. They just looked like a slightly more outrageous version of a courtier of the time, or when at sea were fairly indistiguishable from other seamen or mariners.

Here's a lot more information about medieval period pirates: http://www.skraeling.sca.org/xiphias/newsletter/V4-1-pirate.html

Your persona is a pirate

• You might call yourself a pirate, raider, adventurer (a captain who finances the expedition), but not bucaneer or privateer
• Letters of Marque were given in 16th C England, so you can opperate freely against Englands enemy's for a small percentage tax to the crown (and what cargo they don't know about they won't miss the tax on)
• your weapon might be a cutlas or sword
• You are probably male, but could be a female captain if you had the money (and didn't care about your reputation)
• This is probably not a full time career - you're either a seaman on merchant trips or a gentleman when not on expedition
• At sea you dress sensibly like a mariner of the day - warm clothing, long shirt, canvas slops (baggy breeches), leather or canvas sleeveless jerkin, warm thrumm cap
• When you go ashore you display the sucess of your mission - wearing the most outrageous and expensive clothes you've managed to plunder, or bought with your booty. These might be drawn from differnt cultures, but all reflect the styles available in your chosen region and time.
• If you are a gentleman, your expedition pirating might give you some wonderful stories to tell at dinner parties for the next year.