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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 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 bought my first pair when I was in high school in the early 90's. It was a navy blue pair of pumps from Payless with a silver decorative piece on the front. The men's shoes were on the wall directly across from the larger women's sizes. I must've pretended to look at men's shoes for twenty minutes before I got the courage to go to the cashier with them.

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.

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…

Well today just happens to be a stiletto day, knee high suede Jessica Simpson's. ===== Not even one second look at my knee boots. Must be normal now.

Yes, an interesting, non-judgemental and literate article which could indeed promote the look. The boots themselves are not very appealing - a rather heavy 'shoe' with a wader shaft attached - but I suppose that was to get away from the look of the typical female thigh boot which some men would find off-putting. Maybe something like these would be better - sleeker but still discreet, and with potential for a higher heel if desired:

I think I got my first heels when I was 16 and able to drive. I went to a Payless shoes, and the only memorable part of that trip was me awkwardly feeling I -had- to spew out my fake back story the clerk did not ask for. I kept those shoes and a stack of Mad magazines in a metal lock box in my closet. I think my parents were worried I was doing something illegal as when I returned from a trip to Michigan the magazines were in my closet, no box or heels. Sometime in my tween years I figured out something was up with my gender identity. I liked some girl things, and did not understand why your gender limited your life experiences. By 13 I was hitting a crisis point, and decided to just ‘be me’, and live on my own terms. Back around 1990 non-binary was not a thing. If it had I might have been far more comfortable mixing up my appearance in public.

Heyo. Decided to try a pair of Sneex. Kinda clunky to look at, but they are comfortable to walk around in.

After shattering my ankle nearly a year ago and finally finishing physical therapy, I've been making up for lost time. I've been shopping quite a bit on Mercari and Poshmark over the last couple of months. I've picked up some Lucky Brand sandals, Torrid mary janes, Nine West open toed pumps, Vince Camuto sandals, some Tom's wedges, and my favorites by far, Vince Camuto Frasper heeled sandals in black. I like them so much I got a second pair as backup. Wedges aren't normally my thing, but I still struggle to walk properly in heels. After trying them, I'm really starting have a change of heart.

Hi all: Allow me to set the situation. Today I was wearing a pair of 3”/3.5cm, dark blue, block heel pumps at the office - a pair of shoes that are very appropriate for a professional setting if one wants to wear heels (see photo). Around noon, I decided that I wanted to stretch my legs and clear my mind prior to having to switch gears from one monstrous case to another monstrous case. I figured that I would step out of the building and possibly walk to the medium sized park across the street. I stepped on to the elevator/lift and as it stopped on the floor below mine, two women stepped into the car. The conversation that followed was very close to the following: Woman #1: “It just started raining.” Woman #2: No or not heard response. Me: Oh man…that stinks! I wanted to go outside and walk around for a bit.” At that point, woman #2 looks down at my feet and says, “How can you wear those? I can’t wear heels." The manner in which the comment was delivered did not seem to be challenging me on my wearing of heels or the pair I was wearing was somehow inappropriate. Moreso, it seemed that she was expressing a general disbelief that any person can walk in heels. Regardless, the comment caught me off guard as, usually, comments given by women are very much along the lines of the fact that they love my heels and if I can wear them, then do so! Not to digress, but I often respond to compliments with a very warmly stated, "It never goes out of style to have style" which often gets a laugh or at least a smile! Me: “Oh, they’re very comfortable. The material is canvas, so there is a lot of stretch to them,” which was/is true. At that point, the doors opened and I held out my hand to signal for them to exit first and as they did so, I wished them both a good afternoon. I stepped outside and it was raining hard enough to prevent me from walking to the park. As I thought about it, I should have responded along the lines of “You should see what I consider to be high heels” or moreso, “Because I can!” Not wanting to create a scene, I responded in a nice and professional capacity. Just for clarity, woman #2 was approximately in her mid to late 40s, about 5’ 6”/167cm, and a proportional frame to her height - not heavy but not thin. She was wearing thong style sandals but not flip flops and jeans - effort level of the outfit, about a 2.5 (on a scale of 1-10). Later in the afternoon when my spreadsheets were giving me headaches, eye strain, and seizures, I decided to ask some of the other females in the office, both of whom told me they “can’t” wear heels, why such was the case. I explained to each the situation, and that I was truly curious and sought an understanding of why some women may be able to wear 5”/12-13cm heels at age 80 and others cannot wear 2”/5cm heels at age 20. I was not at all wanting to be judgmental but was only seeking knowledge. The responses I received were not only enlightening but quite helpful. It seems that foot shape and size are the primary reasons they do not wear heels. One woman explained that she has small but wide feet, as well as a low arch, which makes finding a well fitting pair very difficult while the other indicated that she had narrow feet, especially in the heel area. The latter, who is my colleague, added that if she wore a pair of pumps, her foot would not be wide enough to remain in the shoe, and she would walk right out of them regardless of height. She added that she often wears lace-up shoes or those with a strap across the top of foot so as to keep her foot in place. In a sense of friendship and humor, my colleague stated that she has often seen me wearing heels and wondered how I do it as to her, they look very uncomfortable. It is important to note that only one other person who works in my building on a regular basis (my big boss!) ever puts any effort whatsoever into presenting him/herself in a professional manner. As I have expressed on many past occasions, lounging and/or frump (or both) is often the 'style du jour' throughout the entirety of my office building. Likewise, only once in the two-and-one-half years I have worked in my building have I seen a woman wearing heels (higher than 2”/5cm) and/or a skirt for the day. Thus, the only person who wears heels on a regular basis is me, and there are time where I wear my trainers rather than heels to mix up the look a bit. So, was the question posed to me inappropriate or not? Thoughts? Can't get my photo to upload.... This is an on-line photo of the pumps I was wearing. "Midnight" by Aerosoles.

I too have wondered why I have heard that same comment over and over again, "Oh, I can't wear heels." Or, alternatively, "I can't wear heels anymore." I understand that there are some valid physical reasons why somebody can't wear heels, or at least not for very long. However, thinking back to my own experience, I think a lot of these obstacles can be overcome. It's just that overcoming the physical challenge of wearing heels requires a lot of work, and I don't think most women want to put in that kind of effort. Or perhaps it would never occur to them that it's a skill rather than just a fashion choice. In any case, it's generally a conversation that can't go well. This is why I tend to say very little in reply to such comments, and do much as you did, saying something like, "Ehhh, they're really not all that bad."

I have been wearing heels to work (and almost everywhere else) for over 10 years. I have heard the “How can you wear those? I can’t wear heels" statement hundreds of times. Here are some on the reasons I have heard and some I have reasoned myself. (1) Their feet got wider when they got pregnant and they can't get heels that fit, now. A very valid reason. (2) They ruin their feet when they were young by wear ill fitting heels. (3) They never learned how, they have weak ankles, never ran or played sports, so they never strengthen their ankle. (4) They wore running (trainers for the Brits) their whole life and never developed the balance needed to wear heels. I watched a college graduation 10 years ago and you could see those women have trouble walking in heels. (5) They buy heels solely on looks and not fit, so they look pretty but never fits right. Result: the heels hurt their feet when they walk. That leads to them to equating heels with pain.

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.

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.

Tough to remember, because i progressed gradually. All started with 2" block heeled Frye Campus boots and cowboy boots, always looking for cowboy boots with taller heels. I made many thrift store purchases also. My first actual purchase was online, a few pairs of Pleaser boots.

My first heels were acquisition from my first wife in about 1977-78. It had (I think) 2 inch heels. Had them till the mid 1990's when they wore out. In 2011, I determine that my numerous ankle injuries was due to men's shoes not fitting my foot shape, so I switched to only women's shoe. No ankle issues since. I Started with mild 1.5 to 2 inch heels. It took a lot of nerve wracking to get over the clicking sound, but now I enjoy it. In February 2015 I had a (medical) need to raise a heel 4 inch, but I couldn't raise just one foot, so I went to DSW and found a pair of 4 inch heels in the clearance area. Put them on and within a minute found my balance and have been high heels since.

I remember the 90s as being some pretty dark days as far as being able to purchase decent looking shoes. My memory isn't what it used to be, but all I can remember is giant ugly platforms with lugged soles, and the jeans that girls would wear too long on purpose so that the hem would get stepped on and get all ratty looking. I also fail to remember my very first high heel purchase. I can remember my first pair of heels, but I didn't buy them, I actually found them. Inside the bass drum of the drum kit in the high school choir room. I know they were some girl's show choir shoes from a previous year, because I recognized them. I paid attention to such things. They sat in that bass drum for quite some time, probably unbeknownst to anybody but me, and I finally decided that they needed a better home. In retrospect, they were kind of ugly. I'm not going to waste a lot of time trying to recreate their likeness, but they were very 80s looking open-toed pumps with fake stacked heels, dangerously close in lack of height to being kitten heels. And they actually fit me. I remember wishing many times that they were 4 inchers, but alas, they were barely half that. I have to fast forward us about 25 years before I bought actual real heels for myself to actually wear in actual life.

Yes, even if the caption is inaccurate. Shouldn't that read "World of High Shafts?"

Precisely. Regular guys wearing nice boots and outfits that isn't some crazy over the top design for the runway. But, I guess our "carpet" is our day to day travels going about our lives in public.

The wife and I made a Costco run yesterday. Sometimes I take this approximately monthly opportunity to be a little ambitious with my outfit, and sometimes I don't. Yesterday was the latter situation--I didn't have the energy or desire to wear truly "high" shoes. I literally need to warm up for half an hour to wear "high" shoes anymore. So I chose my Söfft ivory sandals (model name unknown), which are effective 3 1/2" heels. While in the store, I was accosted (and yes, that is pretty close to the right word) by a young-ish woman, who demanded to know where I got my shoes. I told the truth, and said I didn't remember exactly. I kind of hate doing that, but these days, not only is it the truth, but I have to inform people that this particular model (pretty much the case with whatever I wear) hasn't been made for at least 15 years, and good luck finding it. Thus far I have refrained from pontificating further on the state of current fashionable footwear, which I find either boring or ugly, or both!

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

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.

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!

It seems that my shoe collection has gained some stability lately, as I haven't purchased any new shoes in about three months. With that stability, I realize that my whole philosophy toward shoes has changed somewhat. I used to say that if I couldn't walk two miles in reasonable comfort, I would get rid of the shoes. I gave lip service to this mantra for a number of years, but now I realize that I have to back off of it because I would estimate that I've never walked two miles in over half my current collection. Not all at once, anyway. It's not that I couldn't potentially walk two miles in any of my shoes, it's just that I don't want to. I pretty much don't walk in stilettos anymore because the heel tips wear out far too fast, it's way too easy to damage the heels putting that many miles on them in the real world, and it's not necessarily all that fun, paying hyper attention to every crack in the sidewalk. Sure, I do it occasionally just to prove I still can, but not on the regular. As a result, I have a whole bunch of dressier shoes that have never seen the two mile circuit, and probably never will. And I will not get rid of them.

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

For me it was never so much the bell but the overall feminine styling. I never fancied cowboy boots, or cowgirl boots either for that matter. For me it started with go-go boots, which really don’t have much of a heel at all, and then sorta evolved. The heels became a part of it, since many feminine boot styles also have heels. In terms of personal style and preference I like block heeled boots. They feel more “me”. I’m ambivalent about stilettos. I love the lines - especially 120mm stilettos - but I’m not sure they are really me. And I’m not sure if that’s residual self consciousness or a sense that they don’t - quite - fit my style. i own two pair of Italian Heels stiletto knee boots - same style (Tina), one with 10cm heels the other with 12cm. I like them both very much and would never get rid of them. But I feel much more at ease in 7-9cm block heeled boots (ankle, knee and OTK)

For sure! For me, it was a gradual process I guess. Always loved cowboy boots, then progressed to higher heeled cowboy boots. Then I looked for higher heeled "cowgirl" boots. I'm trying to remember the first time I actually ordered boots with stiletto style heels, I think they were Pleasers. The progression to wearing high heel boots in public was a slow gradual process as well. So much regret wasting so many years of enjoyment due to self doubt, and lack of confidence...

Congratulations! I have fond recollections of the moment that I decided at long last to buy myself some high heeled boots - in the event, a pair of very nice (expensive) black suede OTK boots with four inch slender (not quite stiletto) heels. I decided to treat it as a bucket list thing and although expensive as boots go, vastly cheaper than the exotic travels that usually feature on bucket lists. That initial purchase has led to my buying several more pair, although nothing like your numbers. I love wearing them though and regret the years I needlessly went without

Usually I forget about the significance of this day until it is past, but for some reason I remembered it this year. Perhaps it is because I didn't realize what was happening at the time, and what significance it would ultimately have in my life. Thirteen years ago this evening, I stepped out for the first time in public wearing obviously elevated heels. In a way, it seems like much longer. In this regard, time has not flown by. It is difficult for me to remember a time when I didn't wear heels, even though that was more than 75% of my life. I'm trying to remember what I did wear on a daily basis. I remember at one time I went through a hiking boot phase. When I played with a country band, I wore cowboy boots pretty much everywhere for a couple of years. I must have worn tennis shoes for a good portion of my pre-heeled life. I really don't remember much about my footwear before 2012. I still keep the Söfft clogs I wore for my maiden outing, but I never wear them anymore. Even though they are leather on the outside, the non-leather liner makes my feet sweat something terrible. According to my records, I have not walked very many miles in these shoes, but I sure remember the first mile. I thought it would never end. Even after thirteen years, I will not pretend to be 100% comfortable in my skin. At times I still feel self conscious, especially when I have chosen very loud shoes without thinking about it, only to end up in a place where it's very noticeable. But still, it hasn't been a bad trip so far, and it doesn't really show any signs of ending.

I finally got around to taking some pictures this week. Because the leaves are back on the trees, I now have a built-in place where the sun won't wash out the pictures, so maybe this will happen more often. I have said before that I am not the type of person to walk through the neighborhood with my tripod (or a companion), looking for the perfect photo op. Having said that, I don't usually photo-bomb like I'm going to today, but somehow or other, I managed to take the perfect set. Usually when I do these things, I take at least half a dozen pictures to get one decent one. This time, I didn't delete any of them. They all came out pretty well. Therefore, y'all have to suffer as a result. Today's shoe selection marks the beginning of sandal season, and I took some new sandals for their first public outing, those being Nine West Wilia3. I have no idea what Wilia1 and 2 might be, but evidently, these are Wilia the third. It's not truly their first public outing, because I actually vetted these with a one mile walk a couple of weeks ago, just to see what category they might fit into in my shoe collection, but this is the first time that others could really see them. They were all right for a few hours, and they're all right to walk a mile. They are not uncomfortable, but neither are they a pleasure to wear. They're kind of just there. Nine West is slipping. These are disposable shoes at a disposable price. They are not leather, they are not supple, and they don't appear to be particularly durable. However, they look kind of cool. On edit: Yeah, posting five small photos instead of two medium sized ones is unsatisfactory. I will not do it again, except in special circumstances.

I just ordered these Freebird Detroit in Red Croc. I had hoped to get a size 11, BUT I waited too long, so hopefully a size 10 works. A 40% off Mother's Day sale was my incentive, $275 otherwise.

Hello, it’s been a long time since I last stopped by HHPlace but I thought I’d share my first heel purchase experience with you all again. It was during a recent conversation with my sister that I thought about this forum and in particular a post I had added back in July 2010. The topic was about the first heels that you had worn and I had responded with a post about the first heels I had purchased back in the 90s (see HERE). I had attached an image of a pair of heels which were similar to those that I had purchased but it wasn’t a particularly flattering image and the heels in the image weren’t patent leather like the pair I had bought but served as a reference to the type of style. With thanks to modern technology, yesterday I took the original image and with some help from ChatGPT I was able to reproduce a near perfect image of the first heels that I ever purchased; a pair of Ravel Black Cross Strap Patent Heels. I was a teenager back in the 90s and had had discovered that despite being male and fancying females I had developed a passion for female clothing, footwear, jewellery and makeup. I had taken a liking to black patent leather too and had nearly died when my cousin offered to let me try on her patent heels one evening after high school. I had said no when put on the spot but inside I was so wanting to try them on. Anyway, I had not long left high school and one evening whilst walking home from College with my sister, we happened to be walking behind some high school girls and I was drawn to the heels that one of the girls had on. On seeing them, in that instance I just knew that I had to have my own pair of those heels and so the hunt was on to find them in the shops. It was great back then as there were lots of shoe shops in my local town centre and so it wasn’t long before I had tracked them down with a little help from my sister to the local Ravel Shoe shop. Inside the shop we quickly located them on the shelf, my sister picked one of them up and gave me a close up view. I excitedly nodded with approval, gave her the cash and she went and made the purchase on my behalf. Pretending they were for her, she asked for a size 8 only to be told that they only had them in a size 7. She looked my way to gauge my reaction knowing I was a size 8 but I didn’t care, I’d somehow get my feet into those size 7s. I remember the sales assistant bringing them out and showing them to her and me getting all giddy inside as I battled to contain my excitement at the thought of soon being the owner of the heels I had wanted so badly. I remember it being a truly magical experience! Amazing how something as small as a pair of heels can have such a hold over you! They soon became my pride and joy too and for months on end I would wear them each evening in the privacy of my bedroom. Purchasing those heels wasn’t the start of the cross dressing but they certainly helped take the dressing to another level at that time. Eventually those block heels would soon be sidelined with my first purge. What came afterwards were heels that were much more sexier than before and now they boasted much taller heel sizes too. Care to share your first heel purchase experience? Was it as magical as mine?

Good luck to you in your recovery. It looks like you've got some pretty solid stuff there--nothing too crazy, but stylish and very nice looking. I don't love wedges either, but they do have their practical purposes!

I hope you keep up your incline ankle lifts. Practice on both side. They're great for wearing heels.

Giege, I have that same pair of pumps in your picture and I love them! Happy Heeling, bluejay

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

Gorgeous!

It almost hurts to think about, but at the time I was just an apprentice, and the year did not start with a "2." I learned a lot on that job. Not only about how to be an industrial electrician, but how to get along with people as well. There were people from all over the world on that job.

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

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 …

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.

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.

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.

Another pair that would look good on men. Believed to be by Biondini, but not sure if still available.

Sometimes I wonder if I ever got the chance to wear heels to work whether I'd regret it or not. I've come to the realization that they're not practical in all situations.

Hi all, After a long time of meaning to post but never executing, I thought I'd just start a new threat to document my adventures in heels. Nothing complicated, so dont expect wonders, but just sharing pictures and this and that. Our neighborhood is pretty progressive, and over the years, they've gotten to know me in heels. This past week, we had some cooler weather at first, so my wife and I were at the local brewery in booties: That said, boot season is pretty much over in this part of Texas, and towards the middle of the week it was already sandals weather again, so we wore these beauties from Jessica Simpson. Clearly, I need to work on a better angle, but I don't like making a scene taking pictures, so under the table / bar snapshots are mostly what happens... Case in point, this was yesterday's choice.