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First off, I apologize for asking a question that I am sure has been discussed ad nauseum in specific threads or in response to other postings. My intention is simply to try and gather input from ALL male members of this forum, not just the half-dozen or so regulars whose responses, opinions, and discussions I have come to find very enlightening, highly value, respect, and admire. Allow me to ask the question and then explain why I am doing so. For those who wear heels into work, what is the highest heel height you have worn and if you do so on a regular/routine basis, what is the average heel height you wear? Lately, due to comments and opinions offered across many postings on this forum, as well as my recent public observations and interactions with others, I have been seriously rethinking my approach to wearing heels in public, all in a good way. I hold no doubt that my approach to wearing heels in public/to the office has been that of a very conservative style. By this, I felt heels should be no higher than 3” – 3.5” (~7.5cm – 9cm), no stilettos, and if worn with a skirt, the hemline should not be higher than just above the knee. Truth be told, all of this has started to “fall by the wayside” as my approach to wearing higher heels and shorter hemlines in public/at the office is radically transforming at an accelerated pace. I have been thinking of recent encounters I have had with women wearing either over-the-knee or tall stiletto boots with short hemlines of their skirt or dress. I was recently at Logan Airport (Boston) and observed a “middle-aged” woman who was “rockin’ out” a shorter (just above the knee) black leather pencil skirt but yet, it seemed appropriate for an office environment. As I strolled through Boston along the “Freedom Trail” I observed many women wearing at or above the knee boots with shorter skirts. This made me realize I am so very removed from any sense of contemporary fashion where I reside and I truly have no concept as to current heel/boot fashion or trends. Thus, that which I once thought was “taboo” in terms of office attire is completely misplaced because I do not know what is being worn elsewhere. A frequent contributor to this forum previously noted that he possessed more shoes/boots than he could possibly wear. This led me to consider my own wardrobe which, in turn, made me consider the question of, if I have heels that are “too high” to be comfortably worn out in public, why, then, do I even have them? I am no longer content in having “only at home” heels and have considered the question of, if I have heels that I realistically will not wear out-and-about for whatever reason, then why have them at all? As a result, I have currently "sidelined" a few pairs until I can figure out what to do with them. I am currently considering purchasing a pair of 9.5m/3.75” heeled leather boots and in time, a pair of thigh-high leather boots with a 2.5” heel. I have concluded that if each of these pairs of boots are worn “correctly,” then what would prevent me from wearing them in to the office, or even grocery shopping? I realize such may be subject to employer policy/restrictions, but if there is no expressly worded prohibition of heel height or hemline (within reason) then why in the heck not do it? Yes, I realize that if I am comfortable doing so, then that is all that matters, but again, provided that it is all within employer attire policy. Some of what I have observed about what others believe is appropriate office attire, such as distressed jeans with more missing material than actual material holding them together, leaves me shaking my head in disbelief. I do not know if I will ever be comfortable wearing stilettos of any height out-and-about as I think the heel would eventually break, but as I have 4” wedge heel boots, why should I rock those out with a leather skirt somewhere? I think much of this transformation is the direct result of no longer giving a d*** who sees me wearing heels/boots/skirt and what s/he may think of it. I think it is fair to state that if I feel comfortable in what I am wearing, them I have no problem in having others see me doing so. Truthfully, my head is now spinning!

Stiletto heels are fragile in the sense that they are very easy to damage from stepping down in some sort of gap in the walking surface. I have never found that the heels themselves are the weak link--it's the shank. For those of you who don't know, the shank is a strip of stiffening material, typically metal, that runs below your foot between the inner and outer soles, and connects the heel with the front of the shoe. I have broken exactly one heel in my life, but I've broken several shanks. Once the shank breaks, it feels like the heel is broken because it just caves in, even though the heel itself is still securely attached. I also have a couple of pairs in that 10 to 12 mm "near stiletto" range, but ironically, they are some of the least stable feeling shoes I own, and it has to do with the shank, not the heel. I'm not making a plug, but I have over a dozen pair of Steve Madden stilettos in various styles, and I've never had pair of Maddens feel anything but rock solid when walking. The heels on these shoes range from about 10 mm all the way down to <7 mm. If you didn't see what you were wearing, you'd never know that you were walking on heels that thin. To be fair, I also weigh 60 kg. That may have something to do with it.

Glad to hear it! I, like you, recently traveled and also did not pack a single item of men's clothing. The reason I did not do so was not necessarily by choice but due to the fact that I recently purged my wardrobe of all clothing that was too large for me! So, I have somewhere around 1/2 items of men's clothing. I would have jettisoned all of it but I decided to hold a few items "just in case." Interesting prediction, indeed! I suppose that depends on what one defines as a stiletto. Would you consider the heels of the ankle boots in the added photo as stilettos? If so, then yes, it is only a matter of time as I plan on where these to work in due time. If no, they are not stilettos, then only time will tell if you are correct.

Start with something low key and ambiguous like chunky heeled ankle boots

I, like CAT, do not have the opportunity to wear heels at work, as it would not be advisable or even desirable. However, just for the record, there was a time when I thought I would never wear stilettos, either. I'm going to make a prediction that it will only be a matter of time before you're comfortable with stilettos.

I wear heels to work almost everyday (maybe not once a year). I like 3.5 to 4.25 inch rise for my hip. I had a pair of lace up Sodas today with a 4.3 inch heel and .7 inch platform. I don't wear skirts (except at Halloween) but I do wear stilettos, both in booties and knee highs form. But then I might also wear my pleather pants with knee high boots (like I did to a busness party this pass weekend).

I have no ability to wear heels or the clothes I want to work,,,,, I am in construction. I will tell you that for almost 13 years I have been wearing heels out, now I wear complete outfits that I put together. I traveled again to and from Tampa and wore LULU skirts, shirts and jackets with gym shoes to run around and a dress with heels and skirt outfits with heels for going out and traveling. In fact, I did not pack 1 piece of men's clothing for the trip. It was a perfect get away!

I have definitely created a two-tiered system with my shoes. First class is for walking, and second class is for showing. Actually, that should probably be the other way around, as I wouldn't wear most of my walking shoes in any but the most casual situations. What this mean is that 80% of my collection is worn very little, and I should probably be more ruthless about getting rid of pairs I haven't worn for a couple of years. Most of the time, but not all, the trouble is caused by a combination of leather upper with a man made lining. That combination does not seem to age well when exposed to oxygen. My all leather shoes do not seem to have this problem, and my plastic shoes seem to have it less. Sandals seem to suffer worse than fully enclosed shoes. Maybe this is a false perception on my part, as once this problem starts happening on a sandal, you might as well throw that pair away, because the flaking is usually quite visible as they're being worn, whereas with a fully enclosed shoe, such as a pump, you can't really tell until the shoes are removed. The latest example of this was when I wore my red Steve Madden open toed mules to church a few weeks ago, and by the time I came home, I noticed I had red flakes all over my toes. Not a good look, and there is nothing to be done about it. They're just gone. I used to have a rule that if I couldn't walk at least two miles in reasonable comfort, I didn't keep the shoes. Nowadays, I do not maintain any such hard and fast rule. I think that I probably could walk two miles in a lot of my "dress" shoes, but I don't want to for a number of reasons.