well, this is a fashion forum. it's very much about aesthetics here (altho it seems to be more about models these days...). so when you can make it aesthetically pleasing, alright!
some of those members who posted earlier in the post, they're simply not aesthetically pleasing. that one guy wearing a loose fit t-shirt with a wide, ankle length denim skirt and high heeled boots? questionable, and it has less something to do with him not being the most athletic looking and rather bald. i'd find it questionable on a woman too.
other members get fully into it, i've yet to see Alejandro looking absolutely ridiculous and i've seen what he wears these days. thing is, he knows how to dress, how to make things work, even high heels he's chosing to be just right. it just goes well with him and his personality and it never looks like he's desperate for attention.
when you can present a well rounded package that makes everything play well together, awesome. if you can't, you can't.
and yes, being able to wear high heels as a man is very much dependent on how you look.