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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

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

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.

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 ...

Well, having to find a 38" inseam is surely not one of my issues. It sounds like you have a long and lean physique, which of course, is perfect for tight fitting women's jeans. Is the inseam length as much of an issue if you wear your boots over the jeans? In other words, can you get away with a much shorter inseam if you wear the jeans inside the boots? For me, I have just experimented with thrift shop girl jeans. I didn't want to spend big bucks not really knowing what size/length would be right for the old "dad bod". I found a pair of "lucky brand" dark blue "hayden" 12-31 stretch jeans that fit nicely. They are low rise, so it seems important having the old butt in decent form to keep them from drooping down, I just wear a belt. I have a dark grey pair of the same lucky jeans/same size, probably donated by the same person. I like these jeans because they stretch so fit fairly tight without feeling constricting. Definitely look nice with my nine west blank stiletto ankle boots, or most any boots for that matter. A few years back, I ventured into the levis store in Vegas, looking for a pair of women's jeans. It seems like styles have changed, most women's jeans now seem to be "high rise", saw no real "low rise" styles. Not a fan of the high rise look though. My go to for years was always the levis 511s, they fit fairly nicely. Tried a pair of 510s years back also, had to face the fact that I am not 29 anymore. The sales person in the levis store was quite pleasant and helpful, I'm sure she realized she had a sale if she just stuck with me while I pondered several styles. Finally, she recommeded levis 512s. These seem to be a combination of 510s, nice tight fit on the legs, combined the a slightly more "dad bod" fit around the waist hips. I really like the way the fit and bought a pair, probably should have bought two pairs, they might be discontinued now!

Same here! Again a combination of winter weather, a muddy towpath, and frankly a bit of holiday laziness. Like you, I’ve worn mid heels as a kind of maintenance heel to keep myself in some kind of heel wearing condition. I’m making mastering 12cm heels a New Year’s resolution though and going to get right back into practicing.

The business does seem to be defunct, with no active links that I can see. But this one may indicate a new (or intended) business, although it is unclear whether that is an active advert: https://www.instagram.com/cowboybootscustom/ I bought one pair of MJ boots several years ago and was pleased with the quality and fit. A shame if he is no longer in business.

I still have my first pair of hh cowboy boots that are Western Ranch. Have had them resoled twice. The toe and heel show wear, but a good polishing hides a lot. All of my MJ boots and shoes were custom from my measurements, so have been blessed with a great fit!! As to the Wranglers, I find the pockets are great!! After Levi’s did away with the ‘original spin’ custom jeans, I tried American Eagle jeans as well as Vanity, BKE, Miss Me even Cruel Girl. Miss Me were great!! But very expensive. American Eagle tends to run thin, but fit great, but finding 38” inseam was hard. Vanity was my go to low rise boot cut until they shuttered. Cruel Girl I loved but could only find 36” inseam. BKE were great too but again ran thin and 38” inseam has been difficult. So for the last 5 years Wrangler has been my favorite. I’d love to hear other guys experiences with women’s jeans with their hhboots!! tightlevishhboots!!!

Same here, love wearing women's jeans, just fit better. My only complaint are the useless pockets! It is great to hear from you again here for sure! Always dreamed of owning a great pair of Western Ranch boots from years ago, should have sprung for a pair back then. I do have a few pairs of MJ boots, not overly impressed. To be fair, they were "returns", or orders that were never shipped. Love my light colored pair with the 5" heels, but they are tough to walk in for any distance, should have stuck with 4" heels. I would give MJ boots another chance though for sure. They were reasonably priced, well constructed, good leather, and looked great.

I can see where high heels would actually be good for the foot. I recently had to get some work boots and decided to get professionally fitted for them. It was found out that my feet have gone from a size 9 to size ten. When I asked how that could be the guy told me its because my feet are flattening out and so my feet are getting longer, but also thinner. So I could see where with heels, and your arch being formed solidity, it might actually help your feet, especially against backpain. I once worked at a job where we had to wear steel toed boots with steel metatarsal plates and EVERYONE went to a chiropractor. It protected your feet from dropped steel, but also kept your foot from flexing with each step. Add in 10 hour days and something had to give and for all of us, it was our backs.

I think you did great! For not being used to them, spending a day in them with all the walks you had is quite an accomplishment 🙂 I'm not surprised that you felt it all over your body. I'm fine in 13 cm heels, but I never wore anything higher than a 11 cm heel to the office. Sure I could wear 12 cm heels, but with all the walking before, meanwhile, and after the office I definitely also would feel it! I'm sure with just a little more practice you'll be fine in your 5" boots. You can join us in the "aiming high" topic 🙂 If you'd rather stick to the "normal" heels that's also fine, there's no need to push the limits all the time.

Hey hoverfly!! just logged in here today after a many years hiatus. Still wearing hhboots after all these years! Still wearing Miguel Jones boots and a few pairs of Steve Madden boots. This past week I bought myself a new pair of boots…. Nothing outrageous. Just a pair of Torrid block heel chunky lug ‘hikers’ boots. I’ve always liked chunky heels and cowboy heels all in the 3-4.5” range. I remember a few of the other guys, most with a penchant for wearing heels and other clothes deemed feminine, but who were not trying to be or look like a woman. I still only wear ‘women’s’ jeans because they fit my tall slender body type better. When Levi’s sold out over seas, I finally found Wranglers Q-baby then Shiloh and Willow in 7/8x38 inseam. Also wear 9/10x38. Good to see a few others still at it decades later! tightlevisandhighheelboots!!

I will stand and lecture for 3 hours at a time. The balls of my feet will burn by the end, but I will go to reflexology and get my feet worked on every once in a while.

The muscular fatigue really came as a surprise to me. I’d expected the burning in the balls of my feet - I’d heard that was a common issue - but instead I had cramping and achy calves. Considering all the cycling I do, I couldn’t believe muscle tone was an issue when it came to wearing heels. If anyone had fir calves it was me - but wearing heels really was like taking up an entirely new sport! I’ve not yet had an occasion to stand for several hours in my 10cm so I don’t know how I’d managed but for a couple of hours I’m certainly fine. I have not tried standing for a long period in my 12cm heels - I shall start building up, see if I can manage an hour standing in them.

Starting later with wearing heels and skipping the youth's foolishness has it's upsides as I can read from you both. Otherwise, muscular fatigue wasn't really a topic for me, maybe that's an upside for adapting quicker at a younger age. Standing for a long time in heels really is the worst, it still gets me until today. In 10 cm heels I can stand for a few hours with a little bit of movement in between, but in 12 or 13 cm heels that's a different story... Merry christmas to everyone 🙂

Let me second those Christmas wishes! I know what you mean about the muscular fatigue. I was not in actual pain, and don’t recall much pain in the balls if my feet, but my calf muscles felt like I’d dine about a thousand toe raises at the gym. It wasn’t exactly painful, but tight and achy. I took the next day off - frustrating, as I was so keen to put them in again!

Just to let everyone know that I had to go out on Christmas Eve to do some last minute shopping. I wore my Land's End , green with white stripes rugby dress which goes to just above my knee, with white tights, red patent knee boots with 3-1/2" chunky heels and a red puffer jacket. Got a couple of compliments, even from a guy on my ensemble. Great day to be out in a dress and heeled boots in a Holiday festive color scheme. Merry Christmas to all my fellow heelers! Happy Heeling, bluejay

I was lucky - having waited so long to try wearing high heels, I decided to splurge and treat myself to a really nice pair of boots. A heel wearing friend, to whom I confided my plan, had also urged me to buy well. And so I did. They were expensive, but really nicely made and fit perfectly so I escaped some of the usual discomfort and blisters that most experience.

I figure at least 10% of the guys who compliment me on my heels wish they had the cojones to wear high heel knee high boots.

I went from 1.5 inch heels to 4 inch heels in ONE minute. Found my balance no problem. BUT I had done years of ankle lifts, so my ankles were ready. An added incentive was I couldn't walk without 4 inch heels. I had a 26+ inch circumference on my calf, a level 3-4 tear.

I’ve no doubt at all about that. I think guys in general are weary of the stifling rules for men’s fashion regarding colours and styles, and would like to inject a bit of theatre into their personal style

In early November I flew in a pair of faux leather pants and knee high JS 4 inch boots. Only one at the airport in leather pants and one of the very few in heels. Be aware @Shyheels if you wear this look, you WILL be noticed. So dress smartly.

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!

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

It is so frustrating to have a quick glimpse at what may be a great pair of heels/boots, only to have the person take off in the other direction, or have the heels covered by long flared pants. I have been known to covertly follow someone to get a better look, but very carefully, never want to seem creepy or rude.

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

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!

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.