He is going to a costume party.
He probably doesn't realize this, but I think he dressed in character of who he is on the inside. Searching for a freedom that doesn't exist today, a thirst for adventure (not really the blood letting kind), a manly man, making his own way on the high seas....
He really is a cutie! Definitely has that Johnny Depp /Pirate of the Caribbean look-a-like thing going on (that is his own hair and beard!) But I am thinking he wouldn't have enjoyed the 'full of the scurvy, missing teeth, smelly going without baths for a year', eeewwe yuck, reality of actually being a pirate.
That is what Halloween is for. Dressing a part, having a good time, an escape from the day to day. Fun.
I hope you have a great time at your costume party, Kerry Lee!