Mel,
I think Rach had a photo in the gallery of her little boy dressed as a pirate?

You could add an eye patch, a bird to his shoulder, or just to carry around, a sword maybe attach it by tying something around his belly?
Ooh maybe a bit of mascara or something else to show a bit of a beard? just rub it in...
3/4 pants?

what about a bag of 'gold'to carry around with him? or a treasure map or one of those scopes they look for land with? can't think of it's proper name ATM!

Nic