This is why Halloween is so popular with adults. Once you get past the lazy Sexy _____ costumes and into the ones that took some thought, you wind up meeting some interesting people. If you take the time to come up with your costume, you naturally start becoming that character in just the decisions of what they would/wouldn't wear because you're already thinking of the back story.
Its like despite being goofier and less conspicuous, they feel so much more free