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Well it happened again. Another convert. Last night, a women waiting for a colleague asked me how high my boots where. She had seen me in several boots and decided to get some herself. I had my Jessica Simpson black faux suede knee highs with a 1 inch platform and 4.75 inch heel. I had plan on wearing my JS suede stilettos, but it was a drizzling all day, so as the memo states, you "don't wear suede in the rain." She had been looking at boots on-line and figure if I could wear boots with high heels, then she could too. Another high heel convert!!!

First may I say that Gige's quick progression amazes me, he has accomplished more in about a year than I have in ten years. And, like you both have said, making progress is a "vicious cycle" indeed. My Mom used to tell me: "you are your own worst enemy...." I think many of us are under the impression (false one) that the rest of the world is waiting outside our door for us to venture out in heels so they can point, laugh, criticize. While it is true people will notice, but no where to the extent we fear they will. Most are too busy to notice our footwear. And for the most part, those that notice will say nothing (another double edge sword for me anyway). I guess we make the false assumption that most others will notice our heels quickly only because we notice the shoes others are wearing. On the other hand, stumbling around in tall heels we can't handle will get us noticed. As Cali put it, you "have to read the room". Venturing out in a short skirt and fishnets will probably get you noticed also. Having negative experiences like this can be a big set back. This is why it is best to start with heels that are somewhat modest. We are nervous enough venturing out in the beginning, so this just increases the chances of stumbling or tripping, which why it is important to start out in heels that are not hard to walk in. Once comfortable/confident walking in modest heels publicly, then we can start to increase heel size and consider some slimmer heels. The only other idea I have is to venture out with a girl or guy pal that is supportive. "Confidence in numbers". I'm always looking for "heel buds" to hang out with. I would be lying if I claimed I never get nervous when out in public these days, but it is infrequent for sure.

We can only hope. I know if I don't wear heels to work, I get a lot of questions why not. My heels are almost always visable. (I have some sky high jeans that cover the foot.)

Maybe your experience is different, but what I'm saying is that there is nothing to get proficient at. I mean, assuming the machine is operating properly, there is nothing difficult about walking in stilettos because they are stilettos (on hard pavement at least). In fact, some things are easier than when wearing thick block heels. My issue is the absolute steepness. I hit a wall at about 4 1/2 inches. If I'm really being honest with myself, it's more like 4 1/4 inches. I had to do a quick run to the grocery store yesterday afternoon, and I broke out some round-toed, 4 1/4 inch stilettos that I hadn't worn in a while to run the errand. Once warmed up, I was brilliant. I even got a sincere compliment from a man (how often does that happen?)! But, at that height, I can feel my achilles tendon straining, especially the right leg, with each step. To be fair, I weigh a mere 60 kg. Perhaps thin heels react differently to more torsional force than what I subject them to, but I don't really notice the difference except when I step in a crack and ruin my heel! BTW, are towpaths actually used for towing these days? If so, by what means?

I have not, that might be something interesting to try, being as I still have one pair of loafer pumps (I have been looking for the perfect pair of penny loafer pumps for years) that has the problem severely. When I finish my latest shoe inventory, I was going to donate the shoes, but before I do, perhaps I'll give some good ol' adhesive a try. I have worn pumps three different times this week, and have zero pictures to prove it. When I did get a chance to snap a photo, the sun was shining so brightly from a bad direction that it would have been a waste of time. I didn't even try. I have come to three conclusions over the past week, however. Number One: There is nothing particularly different about stilettos, except that you have to be a lot more careful about gaps and cracks in the pavement. Number Two: If I wear my pumps more often, they are much more comfortable than I remember them. Even though a lot of my pump collection is not leather, it does seem to shape itself, at least to some degree. Number Three: There is a big difference between a 4 3/8" heel and a 4 5/8" heel. Though I didn't embarrass myself, I still don't feel I'm truly ready for the taller heel. But if I don't wear the taller heel, I'll never get used to it. Didn't we just talk about this somewhere?

Like you, I do have stilettos that I wear while working, so yes, I suppose they’re technically work boots - my favourite being a pair of lovely black suede OTK boots with 4” heels by Jean Gaborit

My favorite work boots are my Jessica Simpson suede knee high stilettos. But then all I do is talk, write, think, and go to meetings. I know, it's a tough life, but someone has to do it.

Nervous and fear 12-15 years ago. Now, I don’t give a f**k I can count on 1 hand how many negative comments I have heard in all my years. to Pebblesf point, other people are so wrapped up in there phones and staring straight ahead they don’t even notice. When someone makes eye contact DO NOT LOOK AWAY OR DOWN. Look straight back at them with a nod or a hello. I have engaged in heel and or outfit conversations as well as conversations that have nothing to do with the heels skirt or dress I am wearing. I will say from experience that 6” stilettos fishnets and a leather miniskirt will get you noticed and it certainly has gotten me noticed. I am headed to the Tampa airport and back to Chicago in about an hour and I am wearing a brown sweater dress and patchwork/color block brown and black stiletto knee high boots. you only live once and I waited to late in life to dress the way I always wanted to. I’m not hear for a long time I’m hear for a good time

Undoubtedly having some supportive and, better still a high heel aficionado who can offer useful tips, hints and critique as well as enthusiasm would be wonderful. And a bit of a unicorn, I’m afraid. My heels, the ones I wear regularly, tend to be modest ones - 3 to 3.5 inch chunky heels in ankle, knee and OTK boots. I’m not so concerned about my ability to walk well in them, at that height and chunky heels to boot, it’s not hard, but would welcome fashion advice about what to wear with my boots - what style/shade of jeans, or style/colour of jumper, coat or shirt, with which pair of boots. I’m never confident of being well put together - and there is virtually no fashion advice columns for men who aspire to wear tall feminine-style boots

At this point in my heeling career, I have a more subtle struggle when it comes to confidence. Now that it is winter, I basically don't have any confidence issues at all. Long pants and heavy coats cover up a multitude of sins. In the summer, however, short shorts and open toed mules expose your every fault. I went through a period a decade ago when I never wore shorts at all, because I felt I would get too much attention. I can't really blame myself, because I think even a cis-woman wearing shorts and very high heels would attract attention, perhaps unwanted. To address Pebbles's point, I did a lot of walking during those first years in what we would consider modest heels. I don't think I necessarily went about it in a very efficient way, because I think I still looked awkward, having no coach or advisor to say, "You look like a clown*." What it did, though, is allowed me to find my feet, literally, and learn how to navigate the real world in heels without fear of actually falling down. I never would have thought, for instance, that stopping at a crosswalk after walking at a pretty good clip for several minutes, would be hard. Maybe it isn't for some people, but I found that coming to a sudden stop after walking was difficult to do gracefully, as I was struggling to keep my balance standing perfectly still. * Come to think of it my wife did, but was unwilling to offer any constructive criticism.