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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

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’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

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.

Compliments from guys are the ultimate compliments indeed!

Sounds very festive! And nice to receive the compliments!

What pair of heels I choose to wear on any given day entirely depends how I feel when I roll out of bed in the morning and what fits as my feet tend to swell a bit while sleeping. Christmas Eve was a "normal" work day for me and when I was deciding what to wear that morning, I felt a strong desire to do "something adventurous" as part of my outfit. I anticipated that the office would be fairly empty for obvious reasons and thus, I decided that the choice of footwear was going to be a "killer" pair of 5" (~12.5cm) beige, block heeled knee boots. I had purchased the boots during the time when I erroneously believed that the higher the heel, the better. It should be noted that the opportune word here is "killer" as that was what they almost did to me! I put together my outfit and following the "normal" morning selfies to document such, I headed out to my car. As I stepped out of my place, I could feel the stress on my knees and ankles from the tall heel but I brushed it off thinking, "I'll be fine as I will not be doing much walking." The walk to my car was a slow one as the heel height very much restricted the length of my stride. I encountered a neighbor along the way and we briefly chatted about "having" to work on Christmas Eve. Admittedly, however, the brief meeting was intoxicating because of the fact that I was wearing a pair of such tall heels out in public and the person who noticing me doing so really did not care about it. This was that which I always wanted to happen. I made my way to my office and took the long and slow walk across the parking lot to the main entrance. Again, I could feel the stress on my knees and ankles, and realized that such tall heels need a slower cadence. The morning when well but at lunch, I decided to head out for a short errand. The first store at which I stopped did not have that for wish I was looking, so I moved on to a second store. As I walked through the aisles of my second stop looking for an item (and noticed some "old-timer" taking a photo of me!) I was in heaven but the discomfort was starting to build. Rather than walk around the store aimlessly as I would normally do so that all of the other shoppers could see me in heels, I found what I needed and headed back to my car. Although I have a habit of parking my vehicle at the rear of any parking lot for many reasons, that day I was regretting doing so as the walk back to my car was rather tough. I made my way back to my office and desk certainly feeling the stress on both knees and ankles. The remainder of the workday was marked by limited walking and by the time I was ready to head home (and after taking two pain relief capsules) my knees and ankles were not "so bad" but now, my mid/lower back was feeling it. At that point, all I wanted to do was get home but I remembered I had a minor error to run while en route. Following such, and a wonderfully given and received compliment from the cashier on my outfit, I arrived home and the boots immediately were removed from my feet. Seemingly, every part of my lower body, as well as mid-back ached from the heels and my back continued to ache for the remainder of the evening. Sadly, I had to promise myself that 4"/10cm is the limit of heel height from this point in time onwards - I just do not think I can handle a heel much taller than that. What is interesting about all of this is that on the previous day, I had a visit with my nurse practitioner and brought forth the issue of joint health and preservation, knees and ankles in particular. I had mentioned that I had been frequently wearing up to 10cm heels, without any problems, and was concerned about the stress that doing so may place on my hip, knee, and ankle joints . The nurse practitioner took a look at my heels, and after expressing her opinion about how ridiculously cute my heels were and that I was so well dressed that day, noted that the best course of action is to maintain a healthy lifestyle and weight, so as not to place extra stress on the joints. So, as much as I may want to continue to wear 5"+ heels, that most likely will not happen any more or only for very special occasions. I am not sure what I am going to do with the boots...they are size 42 if anyone wants them. Here is the outfit I wore on Christmas Eve and that to visit my nurse practitioner.

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 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

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.