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Hi All; This question builds on another semi-active thread but with a different theme of sorts. My question is, if you have encountered another man in heels, have you complimented him and if so, what was the response? The Backstory... Yesterday, I was grocery shopping and as I was exiting, I noticed a young man, maybe in his early 20's, dressed in a cropped tank top, mini-pleated skirt, black leggings, and a pair of black, faux leather knee high boots with a relatively small heel. For those old enough to remember, it reminded me of an outfit from an early Madonna video - not that there is anything wrong with this, it's just where I mind placed it). As I walked by him, I was absolutely delighted by the sight of another man visibly wearing heels in public said, "Great outfit!!" He offered a slight smile, a slight nod of his head, and muttered a hardly audible "Thank you." I really wanted to engage this person to let him know that I, too, wear heels in public, but due to that fact it was rather warm in my part of the world, was not wearing such for the sole reason of keeping cool. I then complimented him on his boots which drew even less of a response. Seeing that he was more interested in looking at his phone and appeared to be waiting for someone else, I moved on and left the store. This was the first time I have ever encountered another male in heels outside of a drag show. Thanks! G

I have no idea how much such shows influence pop culture. I haven't owned a TV for 12 years, and I haven't watched any kind of series for much longer than that. I will say that at least his heels are real heels, unlike those of some other male stars (Harry Styles comes to mind). In other words, even if he hadn't pointed it out, one would kind of notice that he's wearing heels. Even at that, they aren't crazy, and they go with the rest of the outfit.

Totally agree. You just can’t

Sadly, I am learning this the hard way. Whenever someone compliments me on my heels, outfit, or color of my nails, I always stop and cheerfully acknowledge it because I truly do appreciate it. I do not mind briefly speaking to that person as it has led to many positive encounters, which, not to get up on my soapbox, I hope makes for a better world. Sometimes my compliments to another have been met with enthusiasm but other times with only a simple thank you and nothing more. Due to this and a few other recent developments in my life, I have come to the conclusion that trying to nice, polite, and helpful are vices rather than virtues. I know this is a horribly cynical disposition but it is the reality of today's society. Why this is, however, is for another forum.

Over the years that I have been wearing my girls shoes in public, almost all of these infrequent inquiries have been made by women. My wife used to handle them without any comment from me. As for seeing other men wearing girls shoes, I can count on one hand the number of times that I have seen another man wearing female footwear. Then, mostly flat sandals here at the beach.

Nope, nope, nope, nope. You gotta let it go. Do not approach either man or woman in heels and expect to talk. Women are allowed to do this and get by with it. We are not. It's just the way of the world. MAYBE if you're actually wearing heels yourself, and discernible heels (in other words, you'd better be wearing something 3 inch or higher), you get to compliment and walk away. Otherwise, you're just a creep. I've been on the giving and receiving end of that situation. Sorry if I seem a little harsh, but this is a hard and fast rule.