HI, everyone, and thanks for accepting me on this board.
My interest in heels stems from an interest in skirts which started when I was a Boy Scout. Occasionally I'd see photos of Scottish scouts wearing kilts and that fascinated me. But alas, in the United States, there was no place to buy one.
In the 1960s, when I was in high school and college, I gravitated to "Mod" clothing: frilly shirts, bell-bottom pants, that sort of thing. To go along with that I bought some men's shoes with maybe 1 or 1-1/2 inch heels but they were no big deal.
In the early 1970s I was in the army stationed in Germany and discovered a pair of men's high heels for sale on the PX! I guess there was still some Mod fashion going on. They were medium-brown 3" block-heel oxfords and although I got some funny looks wearing them, that was part of the fun.
In the following years I occasionally tried various items of women's closing, mostly underwear and pantyhose so it wouldn't show. Then utility kilts came out and I thought my search had ended except for the price. $250-300 was just too much. But eventually some lower-cost providers appeared and I bought one for $75.
My first outing was at a tattoo show that I attended wearing a black utility kilt and everything else black as well. Tattoo shows, of course, are very counter-cultural and I encountered no negativity at all. In fact, I won first prize for the elaborate piece on my back.
After that I occasionally wore the same kilt around the neighborhood and what do you know: no fashion police, no black helicopters, no circles of people pointing and laughing. So after a while I bought some more kilts, and later some out-and-out skirts from thrift stores.
My wife was incredulous at first but put up with all of it as long as she could set certain restrictions. Her attitude is still grudging tolerance and those restrictions are still in place but as long as I can be skirted 95% of the time I can deal with it.
As time passed I graduated from wearing just utility kilts erywhere to sometimes wearing skirts and then to wearing tights. And that was great except it didn't look right with big clunky men's shoes. So I bought a pair of women's 2-inch lace-up oxfords and that looked much better.
That first pair tended to cut into my right ankle, though, so I experimented with a few more styles, returning those that weren't comfortable within the first minute. (I'm a size 11B, which is easy to buy online but rare in brick-and-mortar stores. Thank goodness for free returns.)
Wearing heels in public was pretty nervy at first but I'd already been through that sort of thing with earrings about 25 years ago, and then with kilts, skirts, and tights. The worst part was the click-click-click constantly advertising my quasi-deviant footwear. But of course I got over that. Occasionally I get, "WTF, hmm, oh well,"reactions but I make that part of the fun.
Since then I've graduated to 3" heels and own about a dozen pairs all together. I do have one pair of 3-1/2 inch heels, and I can walk pretty well in those, but I don't see going any higher anytime soon. I wear skirts and heels 95% of the time except when my wife and I are out together. (That's one of her restrictions.) I have a beard and male-pattern baldness, though, and therefore always present as a man.
I find it curious that so many photos of men in heels show nothing but ankles and feet. I guess the wearers are just interested in the shoes and not in whole outfits. That might be interesting to discuss. Like, when you go out, aren't you concerned about your entire look?