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It's a look I'd like to try

Yes, my heels are all quite comfortable - even my 12cm ones which I struggle to walk fluidly in, are still comfortable. I’ve experienced more pain in badly fitted and designed running shoes than I ever had with heels. But then I made certain to buy well made, well fitting heels. They absolutely don’t need to be painful

They certainly are. The history of fashion is quite an interesting topic. Until I got brave enough to try wearing heels, I never really considered the history and meanings of fashion before. The history of heels is fascinating And you’re right in the 90s and 00s it was not uncommon for men to wear leather trousers - even without a motorcycle!

Yes, heels probably have a bad reputation amongst people of such professions. Although I don't really know why. Is it prejudice or do they really know of many people who have problems from wearing heels? I had my experience(s) with pain, but I don't think they're intended to hurt. In my beginnings I thought it's normal that heels hurt, and that they're only meant to be worn for some occasions anyway. Now I know that heels can be very comfortable, and that's important to me. As much as I love heels, I wouldn't wear them everyday if they would hurt.

I too love wearing both my leather pants and leather leggings. I even have a leather mini dress and leather skort that I wear in warmer weather. I love the look and feel of leather real or imitation. Happy Heeling, bluejay

I'm trying to think if I've ever seen somebody around here wearing leather pants who wasn't riding a motorcycle. Skirts, yes, but I can't recall having seen somebody in pants outside of PPE. I'll be on the lookout. Speaking of looking out, I was at the grocery store yesterday (in heels, of course), and I spied a woman at some distance walking away from me. Soon I noticed heels sticking out of the hem of her pants. She had long hair, and was wearing a camel colored wool coat. At that moment, one of the clerks stepped out of the checkstand area and said, "I can help you over here, sir." I couldn't really say to hold on for a minute, I need to check out this woman's shoes first, could I? So I will never have any context for the heels. Ten years ago, I wouldn't have cared, but now I kind of want to know why someone besides me would wear heels to the grocery store.

Oh, really? I'm a bit surprised, because it's basically a classic stiletto pump style. Good combination! I think generally leather pants are best combined with heels.

I went to the chiropractor earlier this week wearing 4 1/2" stiletto heels, and he didn't say anything. I was kind of prepared for a discussion, but none ensued. It's not happened a lot, because I usually stop in on my way home from work, so it's a non-issue, but on several occasions when I've been in "civilian" clothing, I've changed my shoes to go up there because I didn't feel like talking about it. Maybe that has become unnecessary.

Last week, I was in The Netherlands to celebrate a milestone birthday for my wife. We went to dinner on the evening of her special day and for the occasion, she selected an intimate setting about 2kms from our residence. Given that the notoriously unpredictable Dutch weather was cooperating (No rain, non-hurricane force winds, and mild temperatures) we decided to ride our bikes to the restaurant. My outfit for the evening consisted of a pair of just delivered, custom made, black leather, high-heel knee boots from Noe, my favorite brand, which just happens to be based in The Netherlands. They feature 4.25" heel with a .5" platform and ~14" top circumference. Simply put, they are "to die for" gorgeous! Pair with a very "flirty" grey skirt and black top, it was a beautiful outfit if I do say so! If anyone has ever biked in The Netherlands, they would know that doing so can be a challenge in its own right. Doing so in heels, however, adds a new level of difficulty. Admittedly, the ride to/from dinner had to be done carefully so that I did not damage the heels if the ball of the foot area slipped off the pedals, or I had to come to a sudden stop. The sole of the boots is not rubber such as that found on a pair of trainers, so their slipping off the pedals was somewhat of a frequent occurrence. Fortunately, I made it to and from dinner with no damage to the boots. And I loved being seen wearing my new boots!

I agree with you both on this, as I travel a lot and wear my high heeled boots to many different locations. If you dress for the proper occasion and for the right place, the compliments will come. I luckily have only received compliments from guys and women when I wear my boots. There are a lot of guys and out there that want to and wish they could wear boots and heels like the rest of us.

You are right, you will definitely be noticed. Most won't say anything, but you will feel many stares in your direction. So, having confidence in what you are wearing, and how you look is so necessary. We have to remember that many disapproving looks are truly just envy, whether they come from men or women. The important thing is how you feel about how you look. In my case, I have to be honest with myself, no way I can pull off many of the outfits I might like to wear, this old dad bod just isn't up to it. But, I still think I look pretty good in some nice boots over tight fitting levis or girl jeans. So, over the years my confidence has increased. I can honestly say that I think I look good, and that is all that matters. Needless to say, recieving an occasional compliment refuels my confidence, don't mind admitting that. The other thing to remember is it is important to dress appropriately for the occasion/audience. A tight skirt/hose/tall heels probably isn't appropriate for a football stadium or Home Depot. Cali's advice about "dressing smartly" is very important indeed. My best to all my HHP buds for a happy holiday season and healthy 2026! Don

I'll swear that wearing decent fitting heels/boots actually helps my posture and reduces back pain

Deflated is a good description!

I figure that either we're freaks, or everybody else is just substandard. 😆 I can't really tell you why it doesn't hurt anymore. In fact, I prefer the high heeled position of the foot for most things. I wouldn't want to be stuck in that position permanently or anything, but I do like the way it feels. I suppose it is something that is developed through repetition over time, and I suppose that like any other athletic endeavor, there are some people who are just not very good at it, or have a physical impediment. That would explain why some people claim that even 6 cm is too high for more than a few minutes.

I think in the 90s and early 2000s it wasnt't that uncommon for men to wear leather pants, right? Fashion standards are strange...

It’s a pity that men seem to be so restricted in what society permits them to wear. It’s the same with knee boots - fine if there’s a horse or motorcycle in the picture, but otherwise wearing them is considered odd or effeminate. Strange, really. As for me I rather like the idea of wearing leather trousers with heels.

These boots are gorgeous!

In Germany they're worn quite frequently, also by me. But only by women, men here only wear them for riding a motorcycle as you say 😉 What a pity. Nowadays I also immediately have a look if I hear a pair of heels somewhere. It became a rare occasion.

Those are tall and steep looking. They remind me of Go Go boots.

I love to wear my faux leather pants with my knee highs. Glad to know I'm in vogue. ☺️

The ones I saw didn’t look fake, but at any rate the look seems very much in vogue.

A day in London yesterday, mainly in the Covent Garden, Seven Dials area and along the Strand - a lot of heels, mostly knee and OTK boots with chunky heels. A couple of stilettos and mercifully only one pair of kitten heels. A surprising number of leather trousers, which seem to be much in vogue.

Easy explanation: running shoes are porous and get wet inside when it is raining and in snowy situations.

There are certainly more heels here too in winter than in summer - at least in my experience. Again, boots

It's happened before when I've worn some pretty tame heels to appointments: "Ya know that those kinds of shoes are really bad for you, right?" We have never had a real conversation about it, so I decided to pull out all the stops and wear pointy stiletto pumps to my appointment, as the opportunity presented itself. Not a word, and he even has to pull on my ankles as part of the normal adjustment. I wonder if he has any other patients who wear any sort of substantial heels?

I can imagine that flat palstic pedals will be very slippery. I don't have special pedals, but they're metal and offer good grip. I use them with normal shoes for bike tours and also with heels. They're fine for both 🙂 This will sure be fun!

Yes it very much depends on your pedals! I never got into the modern trend for clipless pedals and the pedals on my bicycles are all old-school quill pedals and my feet never slip on them. But a lot if cheaper bikes and rental bikes have these flat pedals with plastic platforms that can be very slippery when wet. I rodeo e once and being used to really nice bicycle, I was appalled. i think it will be fun to put in my stilettos and ride to a place where i can practice. Come spring I hope to be doing this!

Ah, now I see what you mean. Yes, that seems possible. But even with the most slippery soles I never had that issue. Sure also depends on the pedals you have. Right, cycling to such places is a good idea!

It’s unlikely, but if the ball of your foot slid outwardly on the pedals and you were wearing stilettos your heel could hit the front mech on the downstroke. Unlikely, but I think it’s possible. in any event it’s perfectly possible to cycle in heels, and something I am considering so I can get to places to practice in my 12cm stilettos

Cycling in heels is really no big deal, you're overthinking it 😉 As Shyheels said, the heel doesn't even touch the pedal, so it doesn't matter what type of heel you wear. Only platforms change the feeling of the pedals, but with low platforms this also doesn't change that much for me. I also never had a heel stuck in the front shifting mechanism and can't imagine how that could possibly happen.

There’s no way your heel should get stuck on the pedals. Your heel doesn’t touch the pedal, no matter what kind if footwear you’re wearing. It’s just the ball if your foot on the pedal. Dismounting might feel strange in heels, but that’s all. The biggest problem woukd be the risk of scuffing your nice heels on the chain if you don’t have a chain guard, or getting a long stiletto heel stuck in the front shifting mechanism. If you were careful and pedalling at a measured pace there should be no problem

And now. . . for something completely different! Yesterday it snowed. Again. It's going to be one of those winters, apparently. It's not even Christmas, and I'm already wearing of removing snow. A couple of years ago, I got these vintage boots. Cobbies is the brand name. I got them because they are shearling lined, and I wanted some "heels" to wear when it was really cold. These boots feature 2 3/8" heels, which is right at about 6 cm. In other words, FLAT. Which suits me fine for the work I'm doing. I do consider them low heels in the grand scheme of thing, but they're flats. Let's be realistic. Where things get interesting is the coefficient of friction factor. The forefeet of these boots are quite grippy, while the heels, once covered in ice, are dangerously slippery. This leads to some interesting footwork, worthy of a ballerina or Latin dancer. Walking heel to toe on smooth concrete after walking in the snow can lead to catastrophe, so it's best to do the opposite--toe first. I demonstrated this to my 16 year old. He said do what you got to do. A reheeling with Vibram would probably solve this issue.

I have always worn shorts in the summer, as did my father before me. However, neither of my two sons ever wore shorts after the age of about 10, and they don't show any sign of ever changing. Oddly enough, both of them have legs that are like tree trunks, and yet they have different mothers. They certainly didn't get that from me! I also know plenty of women who never wear shorts or an above the knee skirt. I don't want to say I never do it, but it is easier to wear my beloved wooden heeled sandals with shorts rather than stilettos. Probably absolutely no one outside a certain group thinks about it this way, but to me chunky wooden heeled sandals with shorts is far less radical looking than stilettos with shorts. There is probably almost no one in the general populace who makes such a distinction. @higherheels I always thought the only proper footwear with a Dirndlkleid is none at all, meiner Meinung nach. Certainly much better than sneakers.

Like @mlroseplant, when I started to wear women's shoes in (aka stopped wearing men's shoes), I hide them under longer pants. And those were at most 6.4 cm heels. Then when I had to raise my heel 4 inches I hide them at first. But it was a hot summer, over 100 F (38 C) daily, so I wore shorts and exposed my heels and got thicker skin. Now I wear my tall boots on the outside; yesterday I had my Jessica Simpson black knee highs on and got "that's a fierce fashion statement" from a waiter when I went to the restroom. I have about a dozen stilettos but I have to consider the surfaces I will be walking on. As a result there are only a few days I can wear stilettos. The places I go to now are NOT stiletto friendly, so I rarely wear them. But I will wear my suede JS knee high stilettos with short shorts in the summer. Now "that's a fierce fashion statement."😁

I can understand your issues with stilettos as men, being too girly and so. For me as a girl, this was exactly what got me into them. Only later I started to like block heels too. Although stilettos are more dressy than block heels, I don't feel wrong also using them for more casual occasions. Only for walking on soft or very uneven ground like grass I find them unappropriate. Indeed, I was a bit disappointed yesterday. Fatigue and the pressure on the balls of my feet are my limiting factors. I'm sure I could also walk 300 meters in them, but that would just be painful. After my walk yesterday It was not painful, only uncomfortable. I'm over the days of going over my limits and putting up with pain and rather have a good time and take it slower. I'm also not planning on wearing these boots or the Hot Chicks for extended walks. But being able to wear them for a few hundred meters comfortably would be a very nice achievement and open many opportunities for me to wear them 🙂

I was fascinated by stilettos - aesthetically and for the allure of the forbidden, to say nothing of the intriguing physical challenge of wearing them. Just how easy or hard was it to stride briskly along a city sidewalk or waltz across a ballroom floor in lofty stilettos. The thought that I was never meant to know only heightened the appeal. And yet at the same time it was chunky heeled boots that most caught my fancy. Stilettos appealed because they were the Ultima Thule of boundary breaking, which chunky heel knee or ankle boots I could see myself aspiring to wear every day. i know what you mean about feeling funny wearing stilettos in more casual situations. They are inherently dressy. It’s one of the things I like about wearing stilettos in my home office - when you’re a freelance and work from home it’s a good idea to make at least a bit of an effort to dress as though you are going to work as a reminder to yourself that this is an office, not just your kitchen table, and a place for work. Wearing stilettos is great for that. Nobody just lounges around in stilettos! since we started doing this challenge I have really begun to feel at home in stilettos. They are starting to feel as much my natural style as chunky heel boots. I feel quite proud of my ability to get around briskly in my 10cm boots, even if I struggle with 12cm. I can admire your abilities to walk long distances @mlroseplant and @higherheels remarkable abilities to wear Hot Chicks and her even high new boots. You’ve boot been great influences and examples

Here is a picture of me at church, wearing 11 cm heels, playing the alto horn (or tenor horn, if you are British). On Christmas Eve, no less, in blatant violation of the rule. The other flat-heeled guy playing the trumpet is my son. It wasn't my best outfit choice ever. What's up with those pants?

Couple of days ago, I had to go to Home Depot to get a tube of concrete adhesive. I decided that I would wear my Buffalo Bills sweatshirt dress by Erin Rogers. It was a bit cold outside so I added a royal blue puffer vest. With that I wore my white knee boots with a 4" stacked heel and carried my Buffalo Bills cross body bag. As I approached the entrance, a woman on her way out said to me " I love those boots you're wearing". I replied so do I, thank-you for your compliment. Another great comment for a guy in heels! Happy Heeling, bluejay

I recently had occasion to compare Home Depot and Lowes: we were looking to install a backup generator on our house and contacted both stores through their websites for a quote. Home Depot got back to me within an hour and got all the information they needed to generate the quote, we signed the contract, scheduled the installation for later that week, and the installation went without a hitch. Lowes finally contacted me about 5 weeks later...

Thank you everyone for the support! I will keep doing my thing. If you have stories, HinH & Bluejay, please post. Would be curious how you dealt with more "difficult" situations.

Hiddenheels, Very well described indeed. Seems a realistic representation of what one may face as you venture out semi-dressed en femme. The girl peering into the men’s bathroom is crossing a line I mean imagine vice-versa you’d hear screams! Just keep getting out there and enjoying your own fashion. I bought my first maxi dress a few years ago and wore some Bakers “Peyton” pumps with it and loved the look. I should post it sometime. Thanks for your stories. HinH