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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!

I think my fear of breaking off a heel, especially for a stiletto, has been the greatest concern that "prevents" me from wearing them. I understand that it is the quality, and thus, strength of the shank and not necessarily how well the actual heel is attached to the shoe that may result in breakage. One of the "issues" I have noticed about stilettos is that of what I call "heel flex." I have and had stiletto heels in which, when the bottom of heel makes contact with the ground, it firmly sticks in place but as the foot bed comes in contact with the ground, there is a slight bend of the sole, pushing the top of the heel slightly backwards while the bottom does not move. When the foot is rolled on to the ball of the foot, the heel "flexes" backwards. My concern that the repeated flexing/bending, ever so slight, will eventually lead to a fatigue failure and the heel becoming detached from the sole. This flexing/bending, however, is not limited to stilettos as I have noticed it happening to other heels, even block heels. I am not sure if this is "normal" or is a reflection of the quality of construction of the shoe/boot. I have learned that heel breakage is not limited to stilettos or other taller height heels. Some time ago, I was shopping at a larger retail store while wearing a pair of "flat - heeled" riding boots. Shortly after I entered the store, I noticed that the 1" heel on the right boot was making a strange sound. As I looked at the right heel, I noticed that it was barely attached to the sole as the glue holding it in place was minimally applied. I removed it, placed it in my pocket, and hobbled around the store quite embarrassed by the situation. When I returned to my car, the boots came off and I tossed them into the back seat. When I actually returned to my residence, I noticed that the left heel was starting to come loose from its sole and what followed was a sting of profanity that, last I checked, is still hanging above Springfield, Illinois, and has been known to cause some degree of turbulence for air traffic in the area. What made this situation infuriating is that the boots were a designer brand from which this type of nonsense should not be expected. I glued both heels back to the sole and sank three small screws into each heel to help secure them in place; I had no issues with the heels when I last wore them. The point to this is, what has been echoed in previous replies, materials used and craftsmanship of the product may be the ultimate factor when/if a heel should become detached from its sole, is right on point.

They look good on you whatever you call them. I realize nearly all of my heels which I consider more stiletto than not fit your description of “near stiletto” because at first glance that is what they look like. I think a near-stiletto or stiletto-like heel has become popular as it offers much the same look with more stability. One thing I’ve noticed over the years is heel wearing has strengthened my calves which has helped me whether playing baseball or football from time to time. It’s nice to still have decent footwork at 64. Keep your stride buddy. HinH

Got a couple of pictures this week. One is the church OOTW, featuring a gray color palette, which may be an oxymoron. The second is Casual Saturday, when I decided to wear my new boots, which are rather on the chunky side.

Vibram soles seem to be the best all-round sole for the canals - in my experience anyway. As you say, smooth soles would be disastrous. Gum boots are great for muddy towpaths but not for locks and swing bridges and the like. I like a really sturdy sole. I’m fortunate in having a couple of pair of knee boots with Vibram soles

Having myself often been crew on a UK narrowboat, I would consider that a cowboy boot or similar with a heel that can 'dig in' a little would often be an advantage when working lock gates. It can be difficult to get a grip on the ground when literally putting one's back into moving a gate beam and (as cowboys found when roping steers etc), a boot with a heel gives a better anchor. I agree however that 'high' heels would be a hazard in most other canal pursuits.

As I’ve mentioned before I think I must be the only person living on the canals who owns a pair (three pair in my case) of stilettos. I saw a thread on a canal boat forum listing things boaters never own. Top of the list? Stilettos. And a chorus of snorting joking agreements followed. To be sure only an idiot would try working the locks or doing any of the physical work of moving a boat down the canal in stilettos or any sort of high heel, and they wouldn’t be practical on muddy towpaths. And there is not much room for extraneous possessions on a narrowboat. So I may we’ll be unique. at least a couple of boaters now know I wear stilettos, as I was wearing my OTK black suede stiletto boots this morning while writing. I looked out just before dawn and noticed the light was beautiful so I grabbed my camera and went out on the bow - while I was shooting several went past walking their dogs. I could tell that a couple of them noticed, but nobody said anything. People here may not own stilettos but they are a bohemian lot - were all a bit odd and that’s more or less understood

Mlroseplant, Your curiosity as to the bank lady “may be one of us.” It’s more plausible than you think. Banking is a more receptive environment for either trans people or maybe just someone who wants to present a more feminine image. Iowa is an interesting case of a big farm state which is fiscally conservative but is quite open-minded on a societal and policy level. These factors will bring out more diversity than Iowans have seen in the past. The difference is, as in Wisconsin, these people will be largely be treated with respect. If you went to the bank dressed impeccably with the required heels my guess is any interaction with this bank employee will be good and, since your wearing the goods, your question will be answered. I saw a black trans woman in Menards a week ago walking alone in ankle boots with I’d guess 5.5” heels headed straight to the building materials counter. I simply said “I love your ankle boots” and this person smiled and thanked me. I purposely mentioned the footwear style to send the right message. There’s an opportunity here for a nice interaction and meet one of your fellow community members. Let us know how it goes. HinH

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!