It depends on the person. I have several trans friends who wear heels all the time and I think that it looks awesome. I believe that people should rock whatever they want, and whatever they feel most comfortable in. That being said, I feel like for straight, heterosexual everyday men to wear them it might look very out of place in the state where I'm from as most people here are fairly conservative and do not even know luxury brands but in NYC I could see where it would be considered more acceptable. I wouldn't want my boyfriend to wear them (even if I was comfortable with it, and if he was comfortable with it which he wouldn't be, other people in public would probably be mean to him and I am not ready for that.), but as I said, for trans woman and other people, I think it is cool. As much as I become obsessed with shoes and clothes and the like, at the end of the day, a pair of shoes is just a pair of shoes--I never understood why strangers could be so harsh about that kind of thing.