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I can just picture a female Italian engineer touring the site, impeccably dressed and in heels. And probably extremely competent

I had a similar experience about ten years ago when I tracked down my former room mate at college, with whom I’d been very close at one time. After graduation he’d become progressively weirder - a survivalist conspiracy theorist sort and we lost touch. Decades later I wondered what ever became of him and managed to find an email address. I wrote and we exchanged a couple of emails, fairly distant in tone. He had been seriously into rock climbing and not long after I made contact, when Alex Honnold famously free soloed El Capitan I sent him a note, recalling old times rock climbing. His wife responded - in a distant tone. I took the hint and never wrote back. Best forgotten

The reason I don't see so many heels is because I spent the majority of my waking hours at a construction site. Having said that, I can remember back in the day when a building was nearly complete, the owner would give tours to groups of people (I always assumed that they were employees/bosses at the company). Invariably, there would be several women in high heels during tours through a building under construction. I can recall another job site I worked on where the female engineer would show up every week to check things out in 4 inch block heeled boots. That was the Barilla pasta plant, and the engineer was actually from Italy. That may have had something to do with not only her footwear, but her impeccable sense of style, despite being on a construction site. The concrete floors were in by that time. It's not like she was stepping over clods of dirt in heels.

I'm going to hazard a guess that nothing's ever going to come of this strange little interaction. No reply to my last transmission for two days. Just a "like." I've got better things to do.

Just an up date on some heels I purchase. These Red Croc finally came in. Unfortunately, they didn't fit. They were a size 10 because they sold out of size 11 fast. Great looking shoes!!! Wish they fit. So I exchange them for these, in size 11. Hope they fit.

Very intriguing. Did he say where he saw you? How long has it been since you guys "hung out" together? I'm sure the guy feels very uneasy asking you about wearing heels, but sure seems like the interest is there. Can't wait to hear more...

That is a bit weird. I think if it was me,I’d just leave it. It’s always curious to me how people start off by saying something like I’m not being judgmental and proceed to make clear they are being precisely that.

Got a strange message on social media a couple of days ago. It was a friend from high school who asked in a private message, "Hey look--I am in no position to judge anyone, but I was wondering when you decided to wear women's shoes... Are they comfier, because my feet hurt." This really seems a little off to me for an initial contact message. No "Hey, how's it going? It's been years and years!" or anything like that. As I had accepted his contact request maybe a month ago, I can only assume that he picked up on one of the remarklably few photos of me that show my shoes, and none of those really feature the shoes. After I came home from work, I messaged him with some short answers, and he responded to them with similarly short answers. I'm quite sure he was otherwise occupied, because the conversation trailed off rather abruptly. I'm glad I did not invest a whole lot of time into an explanation. We'll see what happens in the days to come.

@Shyheels one of the reasons I see so many high heels is because I have take on a leadership position in my line of work and take part in executive level meetings with the leaders from other sectors.

I wouldn’t say so. I think it’s fair though to mention the comments and reactions we receive. How frequently one encounters heels or tall boots will naturally depend on where you are - in my case, living on a canal, along a scruffy towpath, that will be fairly infrequently. I can’t help that. It has nothing to do with fashion and everything to do with environment. @Cali seems to encounter quite a few heels in his day to day life and mentions this in this thread.

As you will in a smaller community. I know it wasn't your intention when you started this thread, but it seems that we are the people mostly seen out and about.

That’s a nice bit of continuity!

My very first heel purchase,,,,,,,, and I still have them and wear them!!! Steve Madden Kyle patent leather hidden 1" platforms with 5" heel

I was talking to some people at the boatyard this morning and heard that in a conversation the other day I was described as the guy in the green boat who always wears tall boots. I’m getting known …

As a person who wears short shorts with knee high boots and a Hawaiian shirts occasionally in the summer, I see nothing wrong with the look, EXCEPT the height of the boots. But at 70, I could be delusional (but I doubt it).

Using the word "delusional" is a translation from my wife's English to the King's English, but I think it's a pretty accurate one. The only thing that has changed in the last decade is the scope and intensity of her disdain. Before, she believed that every single person was staring at me every minute we were in public, and probably pointing and laughing. Now, she believes that every person who gives me a compliment is merely teasing me. There is, of course, a kernel of truth to both of these. I'm sure that a small percentage of the time, both are true. Let's face it, I'm not for everyone.

I would like to visit Toronto someday. It just hasn't been a priority. I even have relatives there, some of whom I've never met.

I see the Bata Shoe Museum in Toronto is putting in an exhibition in the history and culture if the cowboy boot. https://batashoemuseum.ca/rough-and-ready/

It needn’t have been anything physical, like her fitness level or body shape, nor about her age. It was probably just a look that didn’t suit her. That happens. Maybe it was something that jarred just your personal aesthetic, or perhaps it would have jarred lots of people. The point is, it’s no good projecting that into yourself. There’s no way you can make such comparisons. I certainly don’t think you’re delusional, or if you are then I happen to share the same delusion as I think you look quite presentable in heels, always thoughtfully put together - and I say that as someone whose own personal tastes do not run to sandals or pumps. telling someone they are delusional in terms of their style or appearance and its affect on others is undermining and cruel. And irrelevant as the only opinion that matters in this situation is you. If you like the way you look, or how it makes you feel that’s what matters. And the same with the woman in the boots and shorts. If that look expresses what she feels about herself or wants to say, that’s what matters.

Yes those social norms are strangling - and they serve no useful purpose. Like you, I look pretty good in boots and feel even better because I am expressing myself.

Same here. So many years wasted with self doubt. I guess one benefit of my advancing age is that I am much less affected by "what others might think". For the most part, I think I look great in boots and jeans. "Too little too late" I guess, but that is OK. I punished my young self so severely, such a waste. My life would be complete if I could help at least one guy get over these silly "social norms" that seem to have a strangle hold on us.

Don't do that to yourself. You have taken good care of yourself and look better than many younger folks. So sorry the wife isn't a bit more supportive, I have similar issues with my better half.

While out shopping the other day, I saw a woman wearing shorts with knee high boots. The boots are what I would call flat, but they did have modest separate heels maybe 1 1/2" tall. Her top was long sleeved and sort of flowy. The shorts were short, but not shockingly so. I approved of her outfit in theory, but something seemed a little off. It was when I met her in another aisle that I realized that the woman had to be at least 60, and possibly more. She was with another younger woman who appeared to be her daughter. The daughter was dressed normally for an American in sweatpants and a t-shirt at least one size too big. Because of hair dye and good physical appearance, I had at first assumed the woman was much younger, and yet there was this indescribable quality that made me think, "Why does this outfit look less than awesome on her?" Don't get me wrong, I'm not being ageist, I don't believe there is an age when women should dress a certain way, or stop dressing a certain way, but this was not really happening for her, even though I cannot point to any one thing. I wouldn't have thought another minute about this encounter, which did not involve any conversation or contact, but here I am, days later, thinking about it for one rather selfish reason: Do I look like that when I'm out and about? I know I shock people for a completely different reason, but I think I do the shorts thing rather better. Perhaps I am delusional, as my wife has insisted I am for some time.

My desire for a pair of go-go boots came from this same time frame - c.1970. It was a general blurring of gender lines in fashion in those days. Which is why, funnily enough, I didn’t actually grasp at first that go-go boots were only for girls. I nearly asked my parents for a pair. I don’t remember quite what it was that clued me in, but I was mortified to find I fancied girls boots. That embarrassment stayed with me for years.

I was in my teens back in the early 1970s. Modest heels for men were quite common then. I bought 2 pairs of boots (high ankle or mid calf) with approx 2" heels. I think from Dolcis, now long gone. I still have one of the pairs, black patent with a gold ring decoration. They're rather fragile now but I still wear them occasionally.