Guys,
You do have to define the term heels and what people's perception of them is. Even the 70's disco era platform heels would cause people to point, smirk at you just as much as you wearing a pair of 4" stiletto court shoes. The difference is the gender the heels are designed for and also the connotations drawn by the style of footwear worn. It is a well known fact than many men dabble "in private" in wearing clothing and shoes designed for women. It is part of "the scene" in some cases and is seen as not normal. So wearing anything that is specifically female will label the male wearer. Of course, this does not apply in ceratin circles where it is viewed quite correctly as a fashion statement, but the Jane & John Doe don't think along those lines. But step out in disco heels and because they know they were made for men, no stigma is attached to the wearer. Because the shoes were made for men to wear, you wear them without even a thought or care for what others around you may be thinking.
It does seem to me that we are trying to go from the classic oxford laceup flat to an elegant slender heeled court shoe in one go. It is really too much of a change for J&J Doe to cope with. Happily, we are seeing albeit slowly heeled footwear appearing for men. Yes it is expensive, YSL, Gucci offerings are eyewateringly expensive, but no more than women are prepared to spend on a shoe, and there are others like Archie Eyebrows and there will be more to come.
In order to progress, manufacturers need to see a demand. A major chain shop like Russel & Bromley - high end admittedly but nevertheless high street - have a 2" cuban heeled mens ankle boot available and that is good news. Also there is a trend to make mens shoes more sleek and thankfully lighter. Drawing no doubt from the female styling.
Thing is to track down and wear the sorts of shoes that are the next step and if the whole look is good, then no one laughs, rather they wish they were wearing the same outfit. Get higher chunkier heels seen more regularly and then pushing the boundary to more slender and stylish heels is a much smaller step.
Simon.