With respect, that's the wrong question. We can't not judge. Every day, every single decision we make, from the time we wake to the time we fall asleep again, involves judgement.
A better question might be something like, "Is it wrong for me to think poorly of the man in a dress?" To that question, I would answer "perhaps." It depends on why you disapprove. A lack of fashion sense or basic slovenliness? Those are fair game. Not comporting himself in the manner "we" think a cross dresser should? Maybe not so much. Yes, yes. I hear you. His presentation reflects poorly on the rest of us, it's true, but I am me and he is... well, whatever he's trying to be. If others judge me by the slovenly man in a dress, it's their mistake. I can whine about it and leave them with their prejudices, or I can do the best I can to show them that "we" are not all like that, that I am someone else, someone quite unlike that.
