My DD (6 y/o) want to dress up at Breakfast with Cinderella, so of course so does DS (3 y/o). He wants to be a pirate. I am planning on letting him do it, cuz it is DW and he can do whatever he dreams of, right? But, do boys usually dress up and as what? Do you have any other ideas for him? Thanks so much 

Moms kept asking me if they could take their daughter's picture with him! He was loving all the attention! He is a bit if a ham.
I would let your ds dress up in whatever he wants. That's the beauty of being young and really enjoying yourself.