Not bad at all!
Well, for one everybody should dig pirate chicks... So that's a plus. The outfits were really well done, except for the lack of variety, I think she could've used more tops to choose from.
I can't really give any points for originality, but that may be a problem with dress up games in general. But, the art work was very impressive! Especially for your first flash. (I don't see any other of your submissions on Newgrounds, so please excuse me if I'm wrong about this being your first.)
Some tweaks that'd help from a dress up game point of view, you could find a better way to organize the clothing so the player doesn't have to dig through it all. Also, it could stand to be a bit larger. From an art perspective, the pirate girl seems dwarfed by all the clothing, and it was hard to make out the details of her face.
Over all, I'm still impressed, and would like to see what, if any, improvements you could make on it.