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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

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'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 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 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 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

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.