It is difficult being original at Halloween if you are transgender or a cross dresser. Unless you are very good, trying to out "sexy" the cis- women is difficult, especially if you are going to someplace where "sexy" isn't in vogue...like to work.
Then there is the problem I have already written about, looking like a man in a woman's costume when you desperately don't want to. In my past, I have had that happen too many times at Halloween parties. A couple times I was mistaken for a "well dressed woman." But again, just trying to be original was nearly an impossible problem for me. So I always relied upon being the sexiest or best dressed woman I could. On occasion I did get the occasional compliment but never won any prizes.
Halloween though, presents as many different ideas there are for costumes and, as always, I can count on Connie to come up with another take: