Do you care what other people think of you? Your parents, your wife, your children? Your co-workers and boss? Potential employers?
If not, the "dude in a dress" look is fine. If you care, you are outing yourself to the world and once you do that you will not be able to take it back.
Personally, I would not do it, I would be all woman or all man and if all woman, I would do it in such a way and such a place where I would not be recognized as my male self.
