With so many other places to "express himself", it blows my mind that someone would jeopardize their job and their income and their reputation, by expressing themselves at their place of employment. Your job is where you go to work for someone, and earn your living, not to express yourself! It appears I am not the only one who feels that way. I would invite the original poster to get back to us and let us know how it all worked out, both now and six months from now.
If someone asked you the best way to jump off a bridge, would you try to tell them. Or would you tactfully suggest that it might not be such a good idea?Umm WRT to the OP that was not the burning question asked by Gale but your interpretation . . . her question was about "how would we advise about outing herself at work (see below). That is what people (myself included) responded to.
Playing devils advocate for a minute here. If one of my strongly male employees showed up in a dress, I might think he was setting me up for a lawsuit, or trying to get a reaction out of me. In any case, it's his decision to make, and live with. I'm done here.