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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!

This outfit seemed to call for boots.

It is purely coincidental that we should be discussing heels breaking away/off the sole when a year and one day ago, one of the most publicized heel failures in recent memory occurred when one of the Taylor Swift's Louboutins gave out during a concert in Rio. IIRC (I'm not a "Swiftee" by any stretch of the imagination!) she pulled the heel off of the sole and tossed it into the crowd. I am sure her Louboutins cost her well into the five figures which goes to show that price is no guarantee against heel failures. You would think that if one should spend such money on heels/boots, especially Louboutins, heel breakage would not happen. But as pointed out, price is no assurance against product failure - even Ferraris breakdown.

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

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 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.

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.

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).

You and me both, mate

Gige- Your progress is amazing, took me so many years to accomplish what you have in months. And, your outfits are great as well. O'Hare is like a second home to me also.

I have a great pair of knee high Zodiac boots that I purchased used a few years ago with this same issue. I can definitely feel the heel flexing and am afraid/timid when I wear the boots because I don't want to kill the heels, and admittedly don't really want to be caught in public hobbling around on busted heel (again). To add to your point, I would say that just because shoes/heels/boots might be from a well known designer surely is no guarantee of quality materials and craftsmanship...

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

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.

Perhaps that is an idea for another topic someday, though it's not "high" heels--one's preference for work boots. I know my own preference has changed over the years, and I've settled on something rather unusual in my trade. I would start the thread right now, but I think some pictures would be rather helpful, which I'll have to take later.

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.

Gige, Thanks for trusting in us to hear your story and get to know you. It is surprising how much we have in common like our choice to also wear things from the other side of the aisle. Your connection to O’Hare Airport made me smile as I worked at Terminal 5 with INS/CBP for 16 years. Finally, my mother was born and raised in Springfield and much of immediate family resides in the city near Jerome. I have many childhood memories of trips down US66/I-55 between Chicago and Springfield starting in the mid-sixties. I live 250 miles/400 km from Springfield in SE Wisconsin. Thanks again for sharing and please keep posting. Our forum always needs new faces and voices. HinH

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

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

I have come to start embracing this approach. My job is a "hybrid" meaning that I can work from either home or at the office as need dictates. Right now, I do a 2-3 schedule in that I am at home on Mondays & Fridays, and at the office Tuesdays - Thursday. I find that at home, I am more inclined to "throw on whatever" and go with it rather than take any time to put together a nice outfit - it's all done in laziness. My wife has long been a proponent of the "dress for work," even at home" because it does much to promote a professional mindset. She has, understandably complained about those who show up to video meetings in bathrobes. I could not agree with you more - live up to your footwear is my approach to every outfit I put together. That which I wear MUST coordinate with my footwear or else it just will not work for me.

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.