While at first I find this concept a little bizarre, for a non-trans male, (for a trans male, is there even a point to the discussion - of course he would wear heels) I don't know if I can't get over that. There are a lot of clothing items only females (or female-identified males) usually wear, but for many of them, there doesn't seem to me to be a clear reason to have it that way.
Now here is my thoughts for male-identified males. If you are the lone wolf sporting high heels and your pants aren't concealing what you're up to, be prepared for people to find it jarring and to question your gender identification and sexuality. BUT, if you are in the right context, (goth club, catwalk), you can probably look daring and cutting edge to the people around you. As well, it IS the kind of thing I could see becoming a SMALL trend at some point for guys...maybe in the next 10 years. When this happens, there will be less and less eyebrows raised and "lemon sucking" expressions on people who notice. It could get to a point where it is a generally accepted look for males to sport (hey, it's okay already to have heels on cowboy boots, so we're getting there), and I think that would be just great.
But, I have to go another step, because of the outfit posted above. When I look at that outfit I think of my trans friend (male to female). I have a hard time seeing a male-identified male wearing shoes like that. Stilletos will probably never become mainstream for guys. It really better suits the smaller, daintier, and more curvy feminine body type. Males are simply built in a more stocky, angular, linear kind of way, and "chunky" heels undoubtably are much more appropriate to flatter this body type. When you wear stilletos (and the pointy toe seems to bring this out even more), you seem to be saying "I don't like my male build, I want a female build", because the shoes you are wearing are not flattering to a male build.
So there you go. I feel stilletos are like lipstick. I think men can look wonderful in eye makeup, nailpolish, and probably several other cosmetics, but I draw the line at lipstick - Men, you are not supposed to have the full pout that we women do, and if you're not trans, I wouldn't sport any other lips than "au natural" or perhaps a clear gloss. Chunky heels on a chunky shoe? Yeah, I think you can look hot and manly in them. Stilletos? I'm sorry, it will just scream "trans" and I will be wondering how much you have saved up for the surgery.
Just one opinion, but I would like to think I'm rather open-minded.
