Shyheels

It doesn’t sound to me like anyone said or thought your footwear was inappropriate, only that for reasons of their own they didn’t wear heels themselves. All of them seem to give direct physical reasons why heels didn’t work for them, not that they were somehow inappropriate for the office

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

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.

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.

That’s a nice bit of continuity!

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 …

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.

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.

My first attraction to feminine footwear was for the shiny white go-go boots worn by a very pretty red haired girl in my seventh grade class. I didn’t just admire them, I longed to have a pair too. At the same time I was also acutely embarrassed by the thought that I fancied wearing girls boots. I put such thoughts out of my mind, or at least tried to, although I still really wished I could have a pair of go-go boots and thought it grievously unfair that I couldn’t. It wasn’t an obsession, this curiosity and desire to wear feminine boots - it was the feminine styling, not so much the heels themselves that appealed to me - it was more like something I’d be reminded of from time to time. Some random style would catch my eye and send my imagination wandering down those corridors again. And always with regret that such a thing was impossible. About ten years ago, I had this damascene moment when I realised it wasn’t impossible. It was only me that was making it impossible. I decided that I didn’t want to go the rest of my life having never worn heels or feminine boots, and so I ordered a pair. I splurged and bought some beautiful black suede OTK boots from Jean Gaborit with 10cm slender - nearly stiletto - heels. They were beautiful and fit like a glove, my first feels. And from the moment I stood up in them I knew it had been worth the wait. I never did get a pair of go-go boots, but I want to…

Fashion is all about contrived obsolescence. Styles are here and gone in weeks and either you buy them or you don’t. It’s a shame but it’ll never change

Indeed walking a towpath in tall boots and jeans, jumpers and high heeled boots in the supermarket will never grab the headlines, but people here have grown used to seeing me in my tall boots - to the extent that one day when I was wearing hiking boots, one of the locals said he didn’t recognise me at first when he saw me from behind

Yes those are very nice - a bit high for my tastes, I like just over the knee, but the heels and overall styling are very nice indeed

I suspect you’re right. They need guys like us on the carpet, who actually wear boots and heels!

To be fair, there is so little style guidance out there for men in heels or tall boots. You can find no end of fashion stories and articles for women looking for inspiration on what to wear with boots and heels, how to pair things up, but for men there is nothing and the few examples one sees, on Instagram or in the catwalk, are generally bizarre, androgynous, or overtly gay and thus offer little guidance for an average Joe who fancies adding a touch of theatre to his look without going over the top.

On one of my early trips to Antarctica back in the 90s I spend several weeks on an icebreaker and during that time obviously came to know everyone - about 90 or so people (crew, scientists, tradesmen working at the bases) After spending time on the base, and changing over the staff, we headed back home again. One night at sea I found myself talking to what I thought was one of the new guys - returning home after a winter in the ice. I introduced myself and asked his name. He gave me a funny look. It was one of the marine biologists, a guy I’d played scrabble with many a time in the preceding weeks at sea - only he’d had a great bushy beard then. He’d shaved it off while we were at the base and I completely failed to recognise him.

Yes, as someone who wears tall boots a lot I always wear skinny jeans so they can fit nicely in the boot shaft instead of ruching up and/or having the fabric billow out over the top of the boot. His boots are so high though - much too high for my tastes - and so loose (again, much too loose fitting for me) he could probably get away with wearing even zoot suit trousers under them.

I saw that article too - or an article anyway. Perhaps there were others. I liked the tolerant tone of the one I read (on the CNN website) It was far from disparaging the notion of tall boots for men. I’m not a fan of the style - too much like waders - but to each their own. It was not outlandish. A positive response to them, as in the article I read, could well help to normalise the idea of tall boots on men. And that would be a great thing!

Context is everything. It had been years and he wouldn’t have been expecting to meet you - and when he did encounter you, his eyes were drawn to your sandals. That’s what his impression would have been based on, and the corridors down which his thinking went. Small wonder he didn’t recognise you. Had you been in jeans and work boots I think he might well have recognised you

I woke up before dawn this morning, noticed some interesting blue hour conditions and decided to go out with camera and tripod. On a whim I decided to be brave and wear my midi skirt and chunky heel boots. It was four thirty and no one was around. I was setting up a shot when I heard a cheery voice behind me - a woman out walking her dogs, with a camera slung over her shoulder. A fellow photographer as it turns out. She must have noticed I was wearing a skirt - the heels were less obvious - but made no comment or gave me any strange looks. We chatted about light and photography. The conversation was as natural as if I’d been in my usual hiking boots and jeans. I went from feeling momentarily embarrassed to prolonging the conversation. It was just two photographers chatting we now follow each other on Instagram

I am the same with my stilettos. I love wearing them, but worry about wear and breakage. They’ve become my office shoes. And I’m quite satisfied with that. I’m never unaware that I’m in heels when I wear them - I don’t need to be out logging my 10,000 steps a day.

Yes those are nice. I’ve seen Leviticus Boots website. More elegant than the ones in the article. I was encouraged by the tone and the hope that if tall boots in general can become accepted as men’s wear, that will open the door to a wider range of styles.

An interesting article about a Swedish actor turning up at the Cannes film festival in a pair of (low heel) thigh boot by Saint Laurent. What was interesting about the article is that the writer did not disparage the idea of men in tall boots, and indeed went into the history of boots as a masculine fashion, and threw the story forward by suggesting that maybe tall boots could be coming back into style. I certainly hope so, and found the tone of the article encouraging. The boots pictures are not to my personal taste although there is nothing outlandish about them. It would be nice if this story did indeed herald a return to tall boots for men. https://edition.cnn.com/2025/05/20/style/alexander-skarsgard-thigh-high-boots-in-cannes