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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

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?

I’ve had back troubles in the past - a ruptured disc a long time ago - and have found that heels really help. Not really high heels - I don’t think 10 or 12cm would help, certainly not 12cm! But 8cm chunky heels are really good. When I had a kid I had a toe injury that had a very beneficial side effect! I was goofing around, running through the house (aged about 12j and managed to break my little toe on the leg of a table. It hurt. My foot swelled up and I couldn’t wear my shoes. It was winter and my mother had a pair of mid heel knee boots that I could get my foot into. And so my mother lent them to me. I was delighted. I secretly wished I could wear knee boots and here was my opportunity. I had sure to take a long time healing. But then winter ended and I had to give up my borrowed boots. Looking back I realise that nobody - not a soul - commented in my wearing mid heel women’s knee boots. There it was - an open possibility to wear heels

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'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.

It's a look I'd like to try

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!

Great boots for snow removal!

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.

Yes, winter can be a tough time for the higher heels. In snowy or icy conditions I also prefer something lower and a block heel, such conditions can even be difficult in flats. But boots with a low block heel can be just as good. It's been like 15 years ago that I last wore any flat boots for winter, and I never had any problems since. This reminds me of a funny story a few years ago. We were (once again 😉) out at a christmas market with friends. Because snow was everywhere I wore a pair of boots with a block heel, something around 8 cm. While at the christmas market, we saw that on a nearby mountain there was also a christmas market which looked nice, so we decided to visit this one too. It was only a small mountain, something like 150 meters of altitude from the bottom and only accessible via a footpath. My husband and friends asked me "are you sure you can handle this path in your heels?", but I had no doubt because they had a good sole, block heel and weren't that high. And I wasn't wrong, it was really easy. Uphill was pretty much the same as with flats, and downhill I even had a bit of an advantage when walking on the side of the footpath where the snow was a bit softer. Because my heels could grip into it. I sure got some funny looks when other people obviously struggled more in their Uggs and such than me in my heels 😀 So this is my proof that heels can be as good as flats or even better in snow.

Crawling about the rocks in high heels would be insane. Sneakers are appropriate in this case. (BUT ONLY in this case.)

Gosh, I wish I could be so casual about wearing 12cm stiletto boots ... I'll get there one day, I hope, but I've sure got some practicing ahead of me ...

I ventured into women's jeans and cords 8 years ago and haven't ventured out. In Levi's I have several 311's both red tag and cords. In Express I have many different styles, mostly skinny, size 10 and some 8's. Some are 'short', I like the short versions for some boots because the stop before the ankles and don't give me extra bulk around the ankles. My boots fit better. I have gotten a few 'straight jeans' and recently I have some skyscraper in size 10 and 8. I just got a size 6, I can get them on and close the button and zip them up, but they are a little too tight for now. Hopefully, I will be able to wear them with a little more weigh lose. Several of my cords are JAG. I get compliments in those all the time. Love the new 4-way stretchable materials.

Compliments from guys are the ultimate compliments indeed!

Sounds very festive! And nice to receive the compliments!

I've had shoes that gave me blisters, but that is not what sticks out in my mind as a beginning heeler. Mind you, I was a beginning heeler at age 45, not age 14. I wish I could have worn heels at age 14, but that's another subject for another time. My first journey in heels definitely resulted in muscular fatigue that I had not anticipated, but it was relatively mild, like having overdone it at the gym or something. It is this trip to the shopping mall that keeps coming back in my stories. I doubt I had blisters, because I was wearing boots with actual socks. I do not remember muscular fatigue in the calves or ankles. What I do remember is having to unexpectedly stand in line for about an hour at a mobile phone store. That damn near killed me. The pain in the balls of my feet was close to more than I could bear, and I tend to tolerate pain pretty well. I cannot explain how a person sort of gets used to standing in 10 cm heels, but that is what has always killed me. Walking 3 km in 10 cm heels? No problem! Standing still in 10 cm heels for an hour? Impossible! Well, it isn't today, but I've no idea how I got here. It must have been all of those farmer's markets I did with my wife over the years. I suppose that was my training ground for standing in heels. As an aside, Merry Christmas to those who celebrate! And for those who don't celebrate, I don't have to go back to work until Monday! Naturally, it's unpaid, but it's a much needed several days off from a place where I don't get to wear heels.

I almost forgot about muscle pain/soreness as a factor. For me it was mostly pain in the balls of the feet and blisters everywhere which caused me the most troubles. I also think it's better to start low and slowly get into higher ones. But as I did it the other way around, I can say that it also works to start high and therefor limit the walking time (which I unfortunately didn't!). It's just not the most comfortable way. The good thing is, when I then started looking for well made and well fitting heels, everything with up to a 10 cm heel was immediately comfortable for everyday wear.

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.

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!

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.

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

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.

Bluejay, Looked at the link and those boots look both cumfy and sturdy. Think they would go well with jeans, skirt or a dress. Don’t have as many boots as some here but live the ones I do have. HinH

I took a bus to a nearby town today to do some shopping. I had thought about bringing my practice heels and practicing but I knew I was going to be doing a lot of walking and carrying a rucksack full of shopping so I went in my chunky heeled knee boots. As you say, both for men and women trainers seem to be de rigueur these days That said, winter - boot season - is the time of year when you will see the most heels. As I was liked around the town I did see a number of women in heeled knee boots. The men, with the exception of me, were universally in ratty trainers. Although I wasn’t practicing in my 12cm stilettos, it was nice to walk about the town in my chunky heels - it’s all good grist for the mill!

Interesting, I didn't know about the differences between womens and mens shoes. Probably also depends on foot and shoe shape. Some pumps I can also put on just by stepping into them, some I have to pull back on the heel to get into. I'd also say that stilettos look more feminine than block heels in general I just came back from my first walk around the block in my new boots. They're definitely harder than the Hot Chicks for such a "long" walk. I can feel it in my calves and also on the balls of my feet. I will stick to shorter distances and indoor wearing for now. The walk around the block was about my limit, so I'll try it again when I had more practice. Still have a long way to go, but maybe I can wear them out soon again for dinner or so 🙂

I spent the entire day yesterday in high stiletto ankle boots. When adjusted for size and platform, the heel height was 10.4 cm. I am not quite telling the whole truth about that. I intended to spend the entire day in 10.4 cm stiletto boots, but fate had other plans for me. As documented elsewhere, I broke a heel about mid-afternoon and had to switch to 10 cm slim heeled boots after that. I would say that hobbling around on a broken heel for the better part of an hour was good practice for 12 cm, but I really don't think it was. It just made me grumpy, and made me look funny.

I had my second shoe failure of 2025 yesterday. However, this one was not catastrophic--in other words, it can be repaired. I was wearing my Aldo stiletto ankle boots to shop at Costco, and I noticed as soon as I stepped out of the car that something was very wrong. The heel on my right boot had indeed come loose, and was flexing wickedly in a way it wasn't meant to flex. I didn't have any alternatives with me in my wife's car, so I had to walk very strangely the whole time in order to keep from damaging the heel further. I prevailed in the end, I believe this shoe can be fully repaired, but it ruined an otherwise enjoyable outing. I'm doing pretty well this year. On an average year, I have about half a dozen shoe failures, and the vast majority of those result in the shoes being reclassified as landfill material. This year, I've only had two, and like I said, I'm sure this latest one is an easy fix. This despite the fact that I've walked significantly further in 2025 than I did in 2024.

@mlroseplant I only know strip clubs from movies or tv series, and am probably even too young to have recognized that "normal" heels were used in the 90s. Interesting indeed, I only have huge platforms in my mind when I think about stripper heels. It makes sense for manufacturers to use the same heel height for a few sizes to save costs. There probably will be many models out there which are manufactured that way. Wow, as if the height challenge is not enough you're also making a distance challenge! 60 miles in a month sounds a lot. I wonder how much I would make in a normal month. For the christmas market on the weekend I chose a pair of 11 cm boots. Up to now I've always chosen some lower heels like 7-10 cm for christmas markets, so it was really nice to wear something different this time. We were there for about 3 hours, so with all the standing it was not as comfortable as with lower heels, but it was OK. I now definitely want to wear 12 cm boots to a christmas market too, but therefor I will pick a smaller one where we won't stay as long.

So I decided to wear heels to Jury Duty. The pants mostly covered things but security noticed that I had heels on and asked me to send them through the scanner. Nothing major to say, as I wore mary jane flats the next time.

I had promise to do several stories from my early November trip. On the first day of the convention, there was not my heels worn, only me and a few others. However the current leader, was in tall stiletto pumps, her normal ware. Although, many women talked to me about heels. However, on the second day there was many 3 inch heels and a number of 4 inch heels. And the third day a lot of heels. I also saw heels (high stilettos) at the up scale restaurants I had dinner at. === I just returned from a Thanksgiving trot. Only saw a few heels at each airport, BUT, and @pebblesf might be extra interested in this, I saw a flight attendant is 3 inch heels coming off a plane. Today at another airport I saw a flight attendant crew from Southwest where 2 women had at least 3 inch heels, one had a 2 inch heel, while the 4th had flats. Very unusual for a non-Asian airline flight attendant crew. I have stayed at hotels where about 90% of the female flight attendants from an Asian airline were in heels; that's where there are 24+ flight attendants (for the 16+ hour trip).

Now that's a nice compliment you got 🙂

Sounds like a nice pair of boots for work. In a bigger size they won't be that steep and comfortable for a whole workday.

So today I pulled out my Nine West leather knee high boots and measured the heel, 4.75 inches, just over 12 cm, no platform. Small block heel. I have these in two colors, wearing the dark red/brown ones today. Haven't worn these in many months but plan on at least 8 hours in them today at work. Don't plan on having any troubles in them.

I walk to be able to walk and wear 5inch stilettos and not buy too many pairs on the way how do you recommend i and other members get there?

Like everyone says, start of with lower block heels. It is unreasonable to expect to be able to step into 5" stilettos and enjoy walkiung. Fumbling around in ill fitting heels that are too tall is a confidence killer. Being confident is just as important as being skilled.

Yes. They imitate German Christmas markets here - badly! I would have liked to have worn my stilettos to the town fete but the walk along the towpath is just too rough. I am thinking of packing my 12cm boots in a knapsack and walking into town, and changing there. Or maybe taking the bus and the train and trying my stilettos at the imitation Christmas market in Leeds

Your Christmas markets in Germany sound lovely - and from all I’ve heard they really are, too. We have imitations of them here in Britain but they are not very nice - expensive, very fake and shoddy. I'm impressed with your going out to a market in 11cm boots for three hours. That’s great. We did have the town Christmas tree lighting event here where I am moored, and with the towpath frozen - instead of muddy - I wore some nice suede OTK boots with 8cm heels. It was about a 5km walk there and back plus standing around - nothing I fancied attempting in stilettos. It was a nice evening. Friendly little town. I think I was probably the only one in heels

Same here. I wear knee boots and invariably have to remove them.

Yes. Make sure they fit well and are well made.

I have too take my heels off to go through security at airports. And I fly in knee highs on the outside.

But make sure whatever you buy fit WITHOUT pain. Life is too short for shoes that hurt.

If you’ve never work heels I’d try chunky 3 to 3.5” to start, than then maybe four inch (10cm) stilettos. Take your time. There’s no rush

Should I go for chunky but higher or lower stilettos how would you suggest i "graduate"?

If you’ve never worn heels before you’re going to need to buy at least one other pair and probably two - a lower heights to get you familiar with the feel of wearing heels. And even then it will take time, patience and perseverance. Five inch heels - or 12cm - is a challenging height even for experienced high heel wearers with years of experience. There is no easy way

Hey, at least somebody is still wearing heels besides us!

Thank you, and I'll let you know that I'm probably taking the last two days of the month off. I barely made it under the wire before this snowstorm hit, which is supposed to last until 6 a.m. tomorrow. Maybe I will take some footprint pictures if the correct situation presents itself. Good luck with your editor. Hopefully, we'll both be back at the 12 cm thing soon.

Congratulations on your 60 mile month! And nice to see that you wear boots! 😊 Ive been stressed and under the gun trying to finish a feature that has turned into a nightmare by a new young and less than gifted editor with adolescent tabloid instincts and who simply doesn’t grasp the story. I’ve retreated to the safe stable height of my 10cm stiletto boots as I write

The last time I was in such an establishment was 1991, and the definition of "stripper heels" was quite different back then. Leave it to me to be more interested in the shoes than the other bits. What dancers wore at that time was what we would consider quite normal, almost boring shoes. Pretty much pumps with four inch heels. Platforms were not a thing at the time, at least not around here. Sometime between 1991 and now heel heights that seem normal increased dramatically, and platforms for exotic dancers got ridiculously thick. To me, "stripper heels" have never really been all that steep, because after all, one has to be able to at least pretend to dance in them, and for the better part of the entire night at that! I can give a very good example of where "the formula" doesn't work quite right. I have over the years owned a few different pairs of a Michael Kors shoe called Oksana. If you buy them in USW 8 1/2, you get 5 1/8" heels (with 1" platform). If you go up to size 9, the heels suddenly become 5 1/2". That's a full centimeter difference in half a size bigger. Because they are Kors less expensive line, they obviously didn't make a different heel for every single size. I'm guessing 8 1/2 was the cutoff for one length of heel, and 9 was the beginning of the next. ________________________ In other news, most of the reason that I have not been practicing toward the goal of 12 cm heels recently is because I have been working toward the goal of walking 60 high heeled miles in a single calendar month. I have come really close a couple of times, but I've never actually exceeded 60 until now. Here is a picture of me (wearing boots, no less) right after I finished walking the last high heeled mile. Although with the new system of proportional measurement, I'd technically have to call these mid-heels, as they are 1/8" (3 mm) short of being actually "high."