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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

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.

I see what you mean--the "refined" is quite a bit sleeker than the original. And yes they ARE work boots! I forgot to mention my muck boots, which I wish I didn't have to own. Mine are the cheapest farm store brand, because I refuse to pay $150 for a pair of rubber boots that I completely despise, and despise doing the work for which they would be required. Those who have spent the $150 for a better brand, such as Muck brand, say they are quite comfortable. I don't doubt it. Having said that, I did once purchase a shiny black pair with a 2 inch wedge heel that are more along the Hunter Refined lines, and those are OK. I've worn them maybe a dozen times over the last decade, as their application is limited. Maybe I'll have to dig them out and take some photos. I would wear those. But they don't make a B width in anything smaller than a 9. Evidently, the only people with skinny feet are people with long feet. I have done the Red Wings women's thing, but back in the day there were only half a dozen different styles.d Maybe it's changed today. @CAT I get you about going through boots pretty quickly. I typically get 2-3 years out of mine, but I also am running two pair at the same time, so halve that. I've heard stories, mostly from people like Shyheels, about hiking boots lasting decades, but I have never been able to get 3 years out of any given pair, even with resoling, which I've done exactly once. Even with careful oiling and the like, boots just get beat to hell in construction. And I'm just a pampered Sparky!