Someone's already beat you to it. The head of York's Philosophy faculty/department, Michael Gilbert is a crossdresser and even started a movement. He's actually a really interesting dude & a pretty big contributor to international argumentation theory.
He walks around York as a woman (his alter-ego's named "Miqqi Alicia" sometimes lol. It all sounds like one big successful troll, but he's perfectly straight (or so he claims). He just gets some sort of release from dressing up like a woman. Only in Toronto can you hold tenure like that and get away with an extremely "abnormal" personal life.
I wonder if this is the same dude I used to have classes with... how long's it take to become head of a faculty these days? ****, I think I'm getting old.