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You all know I go everywhere to heel, Its Monday night and its time to go out!!!!!!!!!!!!!!!!!! Here is the OOTN!

Ok, I've got some time, I might as well tell the story again. I should probably tell this story more often to people who ask me how I manage in heels so well, rather than just saying that I practice a lot. I officially "came out," so to speak, in May of 2012, when I wore my first pair of obviously elevated heeled shoes to a public function. Those shoes were effectively 3 inch, or 7.5 cm tall. All of the shoes I had at the time were platforms, so I am subtracting out the platform in order to give you a better idea of the steepness challenges involved. Later that month, I took my first real walk in these 7.5 cm heels, which was an eye-opener, because I had no idea how tired I was going to get before I got back home. Later on in that year, I moved up to effective 3 1/4 inch, or just over 8 cm heels. By about New Year's of 2013, I had bought some 4 inch, or 10 cm heels, and I thought I was doing pretty well at them. Until I made the decision to actually go somewhere in them. My wife and I needed to go to a large shopping mall, something to do with our mobile phones. I don't remember the exact reason, but it doesn't matter to the story. I proudly wore my new 4 inch ankle boots which I had just purchased the week before, and we headed off to the mobile phone store, which was probably 300 m away from our car. No problem, right? For whatever reason, the store was really busy that day, and we wound up standing and waiting to be served for the better part of an hour. After standing that long in heels, what seemed like a reasonably easy walk into the mall was incredibly painful on the way out. I literally thought I wasn't going to make it back to the car, my feet hurt so bad. I thought I was going to die. Now, 12 years later, it's hard to remember the intensity of that pain, but I remember thinking to myself, "This high heel thing is just a fantasy. Nobody can wear these things all the time!" I became very discouraged. I do not remember how I got the idea to actually start walking in heels for actual exercise, but it took root shortly after that incident, and I went back down to 3 inch heels and started walking the neighborhood, short distances at first. I didn't really try anything much taller than 3 or 3 1/4" for a long time, but eventually, the 4 inch boots which nearly killed me have become not only doable, but easy. I still have that same model of ankle boot to this day, and I really wouldn't hesitate to wear them to Disney World. They've become that natural, and I guess I've managed to train my feet and ankles to deal with them all day, every day without really thinking about it. I should remember this story more clearly whenever I hear somebody tell me that she can't wear heels for more than 30 minutes without great pain. I was at that place myself at one time. What motivated me to try again is still a mystery. In all reality, my life would have been much easier if I had given up back then and figured that all those women who wore heels every day were in constant misery, and that it wasn't worth it. Instead, here I am more than 4,000 km and dozens of heel tip replacements later, and now I'm the freak who can hack the tall heels like they were carpet slippers!

I just got these custom made knee high boots from Sanctum! I ordered them in February, and it took until a couple weeks ago to get them. They are absolutely amazing, way too snug, but all leather, so will slowly fit me perfectly. And because they are custom, they go all the way to my knee, not four inches below.

Cat, I love that royal blue ensemble. That's a favorite color of mine. Last Sunday I wore a white short skort with a royal blue sequin top and my royal blue, patent knee boots. Got several compliments on my ensemble. Even two ladies complimented me on my boots. Happy Heeling, bluejay

If you could magically transport yourself back in time 10 or 15 years, and you were to cross the same street, wearing the same outfit, you'd have had a lot more people video-ing you. The best we can hope for is that we walked well.

Oh mama! That's it! We're having a best dressed of 2026 competition! You in?

Great storys from both of you! The unexpected situations when you have to stand for a long time are something that's unavoidable if you're wearing heels often. I also could tell so many stories about that... It's funny how we're all so different, but the general paths and ups and downs can be seen in all of our journeys. You definitely took me down memory lane and since we're at it, I might as well tell you about my beginnings: I bought my first pair of heels when I was 16. It was the time me and my friends started going to clubs and parties, and since we felt like we're the big girls now, we also wanted to dress like them. Needless to say we weren't nearly as grown up and smart as we thought we were. So my first pair were cheap stiletto pumps with a plateau and much bling-bling 😂 I don't remember the exact model but wouldn't find anything about them anyways because they were no-name. They must have had something like a 12 cm heel with a 3 cm plateau. I wore them the first time for going to a club. It started pretty good but after an hour or so they already hurt really bad. Nevertheless I (and also my friends) didn't want to show any weakness so we just kept on going for a few more hours until we couldn't take it anymore and walked home barefoot. I had blisters all over the place, but that didn't stop me. I always wore them out again when I had the chance to. Looking back I really don't know how I was able to stand the pain. Probably also a part of being young and dumb. And over time it really got better, and I also bought some better fitting heels. But the big breaktrough came when I was 20 and found me a pair of ankle boots with a block heel (around 8 cm). They weren't the type of high heels I wore until then, but I wanted something different for more casual everyday wear. I couldn't believe how comfortable they were, and started wearing them for every occasion where I wore flats before. This was the moment when I properly started wearing heels - looking for a good fit and quality, choosing an appropriate heel height which is comfortable, etc. It was like a reset where I started from scratch and then worked my way back up again to higher heels and different styles. And it's basically where I'm still at now, wearing my heels daily and sometimes trying something new 🙂

I didn't wind up wearing my steepest heels to the recital, but I did wear some pretty impressive looking ones. Yes, they are a full 15 cm, but you have to discount for the 3.5 cm platform. Not super impressive, but enough of a workout over 600 m x 2. The brand is Onlymaker, and they are actually pretty decent quality for being an inexpensive shoe.

I am sure this topic has been discussed ad nauseum and "resolved" long before it was known that the moon was not made of green cheese. A situation regarding my wearing of heels has surfaced within my family and I came to the realization that the confidence I have gained from doing so has spilled into other areas of my life. Allow me to explain. I have younger brother who is deeply conservative on all matters and he informed me (indirectly) that his eldest daughter (20.5 YOA) had tickets to hear Charlie Kirk speak when he was scheduled to on her university campus. He was murdered, however, before the event at my niece's campus occurred. Needless to say, I sent a carefully worded response about the true nature of Kirk's rhetoric towards the transgender community to my brother and noted that I strongly disagreed with Kirk's positions. The response I received was a profanity filled diatribe about how the transgender community is trying to force their agenda on everyone...blah, blah, blah. Also, it was apparent from his choice of words, that, in general, men wearing heels was somehow wrong because it is not in line with his worldly view. I did not dignify his response with my own response, but not to be arrogant and respect for the fact that my brother is in poor health, both mentally and physically, as an investigator for 20+ years, I could have driven a truck through the holes in his response. My line of belief on this, couple with other recent posts I have offered, made me realize that the confidence I have gained from wearing heels has spilled into other areas of my life. I am much more confident about my work, my decisions, and, just wearing tall heels (4"+) in public and not giving a da(r)n about what anyone thinks or feels about it. For the most part, I have received so many compliments from (mostly) women in my office who love my style and color choices. Most of the men do not care but I still have great conversations with them even if I am wearing a mini skirt. This made me realize that if I can tell a family member "I do not give a (long string of expletives not included) about whether a man wearing heels fits in with your narrow minded worldly view" then what is to stop my confidence from continuing on an upward climb? I realize that over confidence can easily become arrogance and want to avoid going down that road. I guess what I am trying to say is that, I will be more than happy to tell my brother that if he can not accept the fact that I wear heels, then that's too bad. I am going to do so because I like and encourage every man I see to do so the same.

The last funeral service I went to provided me with a special treat. As I walked in the woman ahead of me was wearing perfect boots. First I want to say that no one is pickier but me on a shoe design. The point, the heel, the leather were perfection. The heel shape was the perfect old fashioned graceful shape instead of the new straight peg. I'm guessing they cost several hundreds. She walked in them like they were slippers. I'd paid to just know the name brand to just admire them on the computer. As we stood in line I just loved them.

My own sense of style has gotten quite a bit more casual in the last 10 years. When I first started wearing heels in public, I felt obligated to be dressed up as a part of that look. I went through a period of wearing a lot of sport coats with button down shirts when I was outside of work. That was unusual for this town, but not rare. Remember, this was before Covid. People actually used to dress up for office jobs and maybe stop by the grocery on the way home. Were I to dress the exact same today, I would be much more of an outlier, heels or no heels. It is no wonder that my tailor friend lost her job at Mr. B's, which is a men's clothing store. I assume it still is, anyway.

I have the ability to take my lunch period anywhere from 11:30 - 2pm and usually do so around 12pm as it is the half-way point of my work day. It is not at all uncommon for me to head out to the small park across the street from my building and sit in the sun/shade for a few minutes while video chatting with my wife for a few minutes (better signal). The Thursday of the week before I wrote this was a delightful day and I decided to take a stroll to the park in order to chat with my wife who lives seven time zones to my east. I was wearing a gorgeous pair of 4," tan-ish ankle boots (almost pumps) with a pair of medium blue trousers, and matching short-sleeve turtleneck, beret, and accessories. Not to be condescending about it, it screamed style and sophistication. Upon finishing chatting with my wife, I headed back to the office by way of the intersection separating the office parking lot from the park. As I was crossing the street, I noticed a man driving a larger truck carrying a dumpster full of construction debris. I happened to notice, from my right eye, that as I was crossing the street, the individual driving the truck was recording me as I did so. I did a double-take as I was not sure I what I briefly observed was correct. Such enough it was - he had his cell phone out recording me as I was walking across the street. I quickly waived "hi" and continued on my way. I could do no more than shake my head in disbelief - ignorant Neanderthal. Sorry - not the greatest photo but you get the idea.

Well they finally came. Great heel, loved the color, BUT they were slightly too tight at the toe box. The problem is that they are pointed toe heels and my feet aren't. I could get my my foot in, but it was just too tight and since they are synthetic I didn't think it would stretch. I had got these for many reason. I love the color. I now have several in this color range. I want a boot that I could wear when it rained. I have no desire to damage my leather or suede heels, so being synthetic was a plus. I wanted a slouch style bootie, and I have been looking for some time. This also had a feature, a full length zipper, that I wanted. And the heel was decent as well. The search goes on .........................

I stepped on the edge of a textbook and they split apart. I just love this Steve Madden wedge, and the second pair as well. At least 6 years old. Real suede, that why it has lasted the hundreds of miles it has seen. This is now my run around town doing errands pair. The other pair just got out of the box last year But she ain't dead yet!!! Its a clean disengagement, so I plan to glue it back together and get several hundred more miles out of her.

I’d say they passed away and you’re holding a seance

Im interested as to what the limits are when it comes to heeling in public. Do you restrict yourself to a dark alleyway or dont you care? It does not matter what your heels are like or how high. It would be interesting to know what sort of places you wear them. So where do I wear my heels? Well I have been wearing them almost every day for the last 2 weeks. In this time I have been shopping in a busy supermarket (Tesco). Been to my mates gigs a few times (i'm his roadie). Went to see my father a few times. Went to my girlfriends home. Today I even ventured into a busy builders yard for the first time. I dont care where I go to be honest. I have got over the shy stage of wearing heels as daily footwear.

Taking politics with anyone these days is a fraught business. I tend to avoid it altogether and stick to discussing the weather and the day to day minutiae of life. And if that minutiae includes wearing heels so be it.

👍🤩 Thank you for the compliment !!

Sorry - just catchin' up here. Generally speaking, in response to the original question, I will wear higher heels (3"/9cm+) to the office and places I need/want to go on the way home. If I am heading to an event, it will depend on what it is, the weather, the "feel" of it, and other factors. My local library, for example, is having its annual local artist exhibition in about two weeks. It is an early evening event, 5pm - 8pm, with drinks and nibbles. For this, I will forgo heels in favor of a pair of animal print loafers with black pants and a black short sleeve turtle neck as heels seem to be a bit "too much." Every year my local library also presents a murder-mystery play as a fundraiser on a Friday and Saturday evening. For this, I'll step it up a bit and throw on a skirt with a less than 3"/9cm pair of knee high boots. If I was attending a cocktail party or a fancy dinner, my outfit would be made around a 4"/10cm+ pair of heels. I am never in heels for mundane activities like grocery shopping unless it is done on my way home from the office. If I have to head out to run errands or going to an event where I expect to do a great of standing or walking, my trainers are it. This past Saturday was the annual Oktoberfest my town's civic association and as I knew I was going to be walking around, and socializing with the venders and doing "a bit" of drinking, my coral colored Vans were the choice of the du jour.

That's an astonishing remark and presumption by that waitress, but kind of fits in with my impression of the sort of town and region you describe. Somehow, although you say she didn't, I can readily imagine her using the term 'relations' - that too would be wholly fitting with my perceptions of the kind of prim folk who'd have those points of view.

@higherheelsFor us it is hard to parse out people’s attitudes on whether or not it is just my wife wearing high heels, or because we dress nice. It does not help that we live in a very rural area. Just so you kind of know what I mean, my town is comprised of 433 people living on 5 square miles of island. My state is the same size as Ireland, yet has only 1.3 million people. We have to drive 30 minutes to get to a town that has 2000 people, and a one and a half hour drive to get to a town with 30,000 people. So it is pretty rural here. Most people here do not dress up, and by that I mean frumpy t-shirts/sweatshirts and jeans and sneakers. I believe a person feels as they are dressed so my wife and I dress nice, it is just me in dress pants with a button down shirt and dress shoes, while she is in a dress; often in high heels. So they see us dressed up and think we are just trying to impress people. But that is not us at all. In fact, I really dislike people who are fake. The one time my wife wore high heels with jeans was at a local pizza place, and our waitress commented that “she had to hurry to get a check so we could go home and have “relations” because any woman who wore heels, that was what she was looking for”. The ironic thing was, we had five young daughters at the time and we had let the oldest babysit for the first time and just wanted a few hours alone on a date. I don’t even think we had “relations” afterwards. It just struck me funny that she thought a woman wearing high heels was expecting to do that. Kind of presumptuous, I thought. Note: waitress did not use the word "relations", but rather the real word. Relations is used here only so auto-censors are not triggered.

Yes. I work from home - I'm a writer - and I often wear heels because I like to. It's my office and I can wear what I please. But I can certainly understand someone rebelling against the expectation that they wear heels - or some dress code requirement. I think you've touched on one of the joys of wearing heels - and the source of resentment. They are a challenge. Not everyone can do it, or if they can, are willing to put in the time and effort to make it look effortless. To do a difficult thing and do it gracefully and, what's more, make it look effortless, can certainly spark resentment among those who can't or won't do it. And that's more likely to come from other women.

It's really fascinating. @Shyheels regarding the paradox you mentioned: I guess this all comes down to the point that heels are sort of a challenge. Everyone can walk in flats, but not everyone can walk in heels. So one side sees this as a bad thing, and one side as a good thing. Both can be right.

That's a great story @mlroseplant. I can picture the scene and imagine the circumstances - and the discomfort. I have a standing in heels story too - a couple of them actually. Like yours mine occurred when I was first trying out high heels. I'd always fancied heels and wished it were open to me to give them a try without it being turned into some big deal. When at last I summoned the nerve, I bought myself a pair of very elegant knee boots with 10cm heels - fashion classics, the very sort of boots I'd secretly always wanted and wished I dared to by. All well and good. They arrived and they were perfect. Nicely made, soft leather, perfect fit. I'd gone with boots as my f=gateway into heels mainly because I like boots but also because they seemed the sensible choice - if sensible is ever a word you can use to describe stilettos. In all the how-to-walk-in-heels articles and blog posts I'd read ahead of time, beginners were advised to start low and chunky and work their way up. Somehow I thought that didn't include me, but to be on the safe side I figured to get something at offered decent support. I wanted to succeed at this not end up in A&E with a twisted ankle and a dumb backstory. So boots it was. By all accounts they were easier to walk in. After sitting for a few thoughtful moments, admiring my new high heels and marvelling at my daring for having bought them, I stood up!. Wow. Aside from the giddy rush of finally being in heels, my calf muscles clenched up like I'd done a thousand toe raises at the gym non-stop. That was a surprise. Until that moment it had never even occurred to me that I might lack the muscle tone to wear heels. How could that be? I'm a cyclist. I ride a couple thousand miles a year and live in a hilly town. But taking up high heels was like taking up a new sport, one that not only requires a new skill set but uses your muscles in a whole new way as well. It was my first proper glimpse into the world of high heels. I didn't quit or give up but I look things more sensibly after that. A couple of days later, I managed to eat my lunch standing by the counter in my stiletto boots and felt quite chuffed at my progress. Outside a neighbour went by walking her dog. She saw me in the window, smiled and waved. I smiled and waved back, blushing a bit and wondering if she'd noticed I was several inches taller. A part of me hoped she had.

Yes I agree. Heels are contentious. I have found that women are far more likely to compliment me on my boots while men merely observe - although to be honest I mainly seem to pass unnoticed. with the exception of members here I find it far easier to talk about heels, and men in heels - me! - with women than with men to whom even the subject seems taboo

I think I get a lot less static from women about my shoes than I do from men. But, that's just from a purely initial reactionary point of view. That doesn't even touch the "would I date a man who wears high heels" question, and to me that question is irrelevant. Putting the shoe on the other foot, if you posed the same question to men, "would I date a woman who wears high heels" the answer to the question is a little more complex, but I bet there are a substantial number of men whose answer would be in the negative, based upon that fact alone.

It really is! The more I read about fashion as a culture and the history of fashion the more I want to know. Heels are especially fascinating. They are such a paradox. On the one hand they are denounced as tools of the patriarchy, designed to hobble and objectify women for the pleasure of men, yet at the same time they are born with panache by many of the most powerful women in the world, leaders in business, politics, arts and entertain,ent who view their heels as symbols of empowered femininity, spend small fortunes on designer help and speak of the emotional lift and sense of empowerment that comes with putting on a pair of stilettos and string into a meeting. Men are expected to admire - lustily - high heels on women but are told from birth they mustn't ever even think about trying on a pair themselves. Who can't help but e fascinated by all this furore and taboo?

I'm much there same, but prefer almond-shaped toes. Living along a towpath makes things difficult as I don't are to ruin my boots or break an ankle!

Epically hideous

I remember in the 1980's there was a segment on 60 Minutes about women... gasp... changing into sneakers to commute to work in the bigger cities then changing to their high heels. 60 Minutes was and still is a news show that featured longer running stories, about 20 minutes long instead of 2 minutes like most news shows. Anyway, I remember it because it was a huge deal back then. The women were like, "you wear high heels on city streets and in subways and on busses then and see how you like it", while the men they interviewed hated the new trend. Those men would really hate the trend now... women just wearing sneakers all day, even in the office. My wife lives in her heels, but it is actually other WOMEN who curtail her efforts far more than men. They tend to have snide words about her wearing them, going as far as to call her a "slut" for wearing them. I think it is just jealousy myself that they feel guilty for dressing like a slob, or insecure that her husband might look at my wife. I am not really sure, but by far other women make wearing high heels for my wife more of an issue than it really should be.

Impressively high for what amounts to a 1.2km - ¾ mile - walk! But to borrow a phrase from a dong near to my heart, those heels look made for walking. You should see the towpath here - most unsuited for walking, even in Vibram soled hiking boots. Fortunately I have some very nice knee high boots with sturdy soles and low heels so I can keep up my style for tall boots. And on the cold mornings, such as today - down to freezing with thick ice firming on the boat - I have my heavy suede OTK boots with 8cm heels. Love these!

That’s impressive - a 600m walk in week in your challenge height heels. I’d love to go for such a stroll in mine, but I’m really struggling to find a place. We had two inches of rain last night and now the towpath is unpleasant even in heavy Vibram soled hiking books.

I also had a demanding week, but may break out my highest presentable heels today. I am to attend a music recital this afternoon, which will involve about a 600 m walk each way. The key for me is warming up a little bit first. Once I get to that height, I can't just put on my shoes and go. There has to be preflight.

I’ve been lured away into mid-heels. Very heavy rains and temperatures down to 4°C have prompted me to dig out my heavy suede OTK boots with chunky 8cm heels. They are lovely and warm and very appealing on nippy mornings in the boat. We’re at that tricky transitional point in the year when it’s nippy enough in the mornings to want warm boots but not quite nippy enough for me to want to start the coal fire - yet. The daytime temperatures are a pleasant 15°C or so. i can change into my stilettos in the afternoon

I stand corrected - at least one of my group wears heels apparently. And when I think about it she was the one most likely, a southern lady. I didn’t see her heels but she referenced them in a conversation we had while attempting to do a walk around one of the lakes only to find it was flooded. She was not happy about getting her hiking boots wet as they are going back to America tomorrow and she’d planned to wear them in the plane, saying that she didn’t want to wear her heels in the airport and on the plane. From which I deduced she had brought heels and presumably wore them after hours. And now that I think of it she was also the only one in the group that was familiar with the story about men in heels back in the 17th century …