But if you're thinking about doing this to your dog, you need to be smacked.
Your dog doesn't want to dress up like Princess Leia and all the other dogs are going to make fun of him. Even if it is the only day your dog can dress like a whore and get away with it.
I don't care how cute you think it is, it's just wrong. He won't even be able to look the other dogs in the eye as they sniff his butt. And no one wants a dog with low self esteem.