He looks like Conan O'Brien in the face.
I get that he wants to do this (become a woman) and shouldn't be given grief for it, so that's fine, and I get that since he's a public figure he might want to do some of this publicly in the name of enhancing public understanding and thereby helping out similar people that don't have the advantage of being famous so that's fine too. But there is a line between all that on one hand and personal indulgence on the other and I think that doing photo shoots with Annie Lebowitz on the cover of Vanity Fair may be on the other side of that line.
"Look at me so you'll learn about people like me" is one thing, "Look at me just because, well, I want you to look at me" is another. This feels like the latter.