Leaderboard

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.

Early morning outfit

Here are my new boots, Light brown suede leather

If I had answered this question on the day it was initially posted (which, incidentally, will be one year on the day after I complete this post) I would have said "Nope!" "Nada!" "Nein!" "Nyet!" etc. This was still in the time when I was wearing heels in private. As of today, however, my answer would be "You bet I am wearing heels!" I see it as a matter of confidence coupled with an utter lack of concern about what others may think and if they should have a problem with it. As noted yesterday, I went to the dentist and it was the first time I was out wearing boots and a skirt while not in the company of someone who knows me. Then in the late afternoon, it was a visit to the (new for me) nurse practitioner, but dressed much more business like in a pair of Aerosoles pumps due to the warmth of that time of day. Today, it was the eye doctor in a pair of ridiculously cute Naturalizer slingbacks. Each and every time I entered the building for these visits, I did so without so much as the slightest sense of hesitation or fear. I marched right up to the desk, and stated my name and appointment time. I did not stop to look around at any of the other individuals who may have given me a second look or felt it necessary to do so. If anyone muttered a negative or disparaging word under his/her breath, giggled, or whatever, I did not notice and more importantly, I did not care. Then, when I got home, I had a bit of a walk from my garage to the front door my place. As today I was carrying my computer bag, bag of my case files, lunch bag, purse, coffee cup, and fumbling for my keys, I thought I had passed by hundreds of people and guess what, I truly did not care if anyone saw me. In fact, I hope some of the women around my complex did as they could sure use some fashion tips! I have progressed to the point where I actually WANT others to see me wearing heels and when I have an appointment, I make sure my heels are fully visible. I can not explain it, but there is a huge RUSH (favorite band, btw) that comes over me knowing that others can physically see my heels. I guess that it comes from always believing that I would never be able wear heels out it public to now, actually doing so. Several weeks ago, I was out grocery shopping while wearing a pair of what pants (trousers for my UK friends) with white Espadrilles. A young man stocking shelves noticed me and then gave me a very obvious second and surprised look. I made nothing of it and went to the next aisle. As I thought about this encounter on the way home, I came to the realization that my approach to such reactions is simple: "I'm queer...deal with it." I have not had to use such a strong approach and I hope that I never will. There are two points that have really helped build confidence - accepting who I am and fully expressing that beyond just wearing heels, such as what clothing I wear, accessories, and the like. I realize that how I approach this may not be for everyone and that's totally cool - I'm completely down with that.

Here is the outfit from 2 weeks ago, and yes it was f'ing cold !

I've been browsing this site for a long time. But after my most recent escapade I knew I'd have to share. I want to make a post detailing my history a bit as I've found other smiliar stories and experiences informative. In the meantime though I will share my boldest public outing. So the plan was simple go out in the early AM in flats. Walk to a remote area change into heels, walk around a bit. Change back, walk home. Easy. My biggest problem though is what pair of heels? I bought some bright pink mary Jane's with a slight chunky heel and a nice t bar strap. About 3 and 3/4 of an inch tall. I only intended to wear them at home because they were so blatantly feminine and bright. But they fit well and I can walk in them comfortably, they also can be walked in without being incredible loud. That is if you walk with good technique. I figured that I wouldn't even see anybody and for some reason I picked them for my walk. So I got dressed. Threw a hoodie on slipped into some old ratty sneakers grabbed my heels and head out the door. This was nerve-wracking. But I tried my best to bolster my confidence. Why would I a man be walking holding a pair of bright pink heels? Maybe my GF left them at my house and I'm dropping them off, who knows. These are the mind games I play so I don't feel so awkward about the whole thing. As I walked I ended up at a small stair set. I sat down and took off my sneakers. I slipped my heels on. I took a couple steps and they sound alright and I can walk alright. However I began hearing voices coming closer and closer. I panicked. I frantically tore my heels off and just in the nick of time I was able to get my sneakers back on and as they rounded the corner I began to walk away. At this point my mission felt fubar. For some reason there was a relatively high amount of activity for that time of night. I began to feel discouraged. I also grew paranoid that it was some kind of security and they'd follow me. Thankfully I kept walking and they didn't. I wanted to call it quits but I couldn't turn back and possibly run into whoever that was, so I kept marching forward. Again I saw a man perhaps leaving a late shift or arriving for one. Again the activity scared me. But I doubled down and kept walking. I had now made it to a large parking lot and I knew that there would be nobody there. So I found a big set of stairs sat down and put my heels on. I left my sneakers sitting there and begin to walk. If I walked either heel to toe or tried to land my foot evenly my heels weren't too loud on the concrete. I felt my confidence begin to return. I felt comfortable walking and with my jeans partly covering my feet I felt reasonable safe. So in a spur of the moment decision I decided to go back for my sneakers, but not to change back. I picked up my old sneakers and found the nearest trash can and tossed them. Now I couldn't chicken out. I'd have to walk the mile back home in heels. Well unless I wanted to do the walk of shame and walk barefooted on the wet ground. I felt relatively confident, I knew the area well and I could navigate the quiet darker places and I'd only have to risk one section on the way home. So things went smoothly, well besides the fact my feet already hurt and I was was only a quarter of the way. I couldn't change my mind now! So I was beginning to reach the tricky portion of my walk. I knew that this was a sort of choke point between two sections of town and I would be more likely to see somone there. Surprise surprise as I was thinking this I rounded the corner and a young man was walking right my way about 20 feet ahead. I had no time to panic or hide. I just kept walking. I even instinctively made eye contact and nodded but they just stared straight ahead and kept walking. I was a hooded dude in jeans and pink heels I wonder if he even noticed haha. Either way I survived and the rest of the walk was uneventful. My worst case scenario happened and it was fine. So that was my little adventure. I have more to share in the future. If any of yall got questions id love to hear them. Thanks for reading. Also I've never been very good at writing so hopefully I conveyed this story decently enough and any grammatical stuff wasn't too egregious. -Goose

When I repainted my first place I wore my tallest heels trim the edge where the wall and ceiling meet. A step stool might have been more comfortable, but this was more fun.

Merry Christmas, everyone!

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!!!

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

This outfit seemed to call for boots.

I had an interesting shoe wise day. I had 1.5 hours free in the afternoon today so I went to a large mall near work. First stop was the large Women's Macy's with a very large shoe department, saw nothing of real interest. Then over to an Aldo, nothing; then to the Steve Madden store. While I was looking over what they had, the manager told me he "could only last 3 hours at most in heels like yours." We chatted for a few minutes and I moved on. I looked at Norstrom's shoes, again nothing of interest. Walking back thru the mall, a young couple walk up to me and the guy said "i really like you heels." (I bet one day soon he will try a pair on.) Last stop was at Forever 21, I was looking for a small chain for a Halloween costume, but they didn't have it either. Exiting the store a young girl was filling out a job application, looked up and said "I just had to stop you and tell you how much I love your heels." Today I had a pair of Flexx straight leg jeans with over calf boots. So only a bit of the heel showed. It has been months since I had this much interest in my foot wear, especially in less than an hour and a half.

I bought yet another pair of Steve Madden pumps, model Daisie. I bought them because they were purple. Only once I got them, they were only purple-ish. I don't know what color you would call this, but I wore them for the first time today, with pink and salmon attire. I don't really have anything purple to wear with these shoes. As you can see from the picture, they are tall, but not super tall, coming in at 4 3/8". The heels are super skinny, though.

Here are my latest. I got these in a thrift store for less than twenty dollars in mint condition. Gray ankle boots and the brand is Sam and Libby, and they really look great with the 3 buckle detailing on the side. These probably won't take long to get used as I already have an outfit planned for them.

Probably to most likely...yes! I apologize as this post will either make me look indecisive or like a politician trying to backtrack on earlier comments. A few situations have occurred, however, that are worth exploring and has me reconsidering my previous positions on topics covered in this forum. I think it was in mid-July when I was at SLAM (St. Louis Art Museum) wondering one of the exhibition halls when I encountered a young woman wearing a black sweater, a midi length black and white patterned skirt, and a pair of black, 4" "funky" heeled boots. I casually approached her and as I always do, explained that I did not mean to be forward, rude, or aggressive, but simply wanted to let her know that her outfit was beautiful and as a boot lover, I greatly appreciated her wearing such high heeled boots, especially on a summer day in St. Louis. In short, she explained that the boots were Vince Camuto and were supremely comfortable to the point that she frequently wore them to her office. We spoke for a few minutes about wearing heels before heading in our separate directions. Next, a few weeks ago, I had to physically go to a branch of my bank to conduct some business that I could not complete online. I was dressed rather "mildly" in that I was wearing blue, just above the ankle jeans, blue vans, and some top - nothing fancy and rather casual. The banker with whom I met that Saturday was wearing an incredible outfit the likes of which have not left my mind. The woman was probably in her early 50's and had a very lean figure proportional to her height. Her outfit, however, was insanely gorgeous. She was wearing a black or very dark blue, long sleeve-mid thigh dress which buttoned all-the-way down the front. The sleeve cuffs, collar, the tops of the pockets on the mid chest area were white - it fit her like a glove. Her footwear was a pair of either creme or very light beige over-the-knee boots with a ~3" heel. When she asked me how she could be of assistance, I responded to the effect of that the first order of business was to make it known that her overall outfit was "stunning!" My actual banking business took no more than three minutes but as there were no other customers in the waiting area, we spoke for about 15 minutes about her boots, brands of footwear we like (e.g. Jessica SImpson, Steve Madden, and Vince Camuto) and where we shop. All the way home, some 90 miles, I could not stop thinking of that outfit. I had come to the conclusion that if she (and the woman from the first encounter at SLAM) could and do wear such beautiful outfits, why can't I do the same? Then, today on a much needed break following a horribly stupid morning, I read a short article about "appropropriate" heels for work/office. The writer (a woman) noted that, as has been mentioned here (ad nauseum, I am sure) what is appropriate footwear/heel height for a professional environment is truly up to the wearer of such to decide. She (the author) noted that, generally speaking, 3-3.5" is usually "the limit" of heel height for professional settings but again, the idea of what is "appropriate" may be a confluence of multiple factors such as personal tastes, company policy, etc. The writer seemingly cautioned against wearing heels higher than 3.5" because of issue of practicality, lack of grace when walking, and other similar concerns. All of this started me thinking about what heels do I actually wear to work and what heels do I WANT to wear to work. I have a few pairs of the "Taken" model boots from Giaro I purchased via Shoebidoo in Utrecht, Netherlands. They feature a 12.5cm/5" block heel and I have always wanted to wear them out somewhere. I have worn my black pair out once albeit to a drag show, so they really fit the mood of the event. Despite the tall heel, they are easy in which to walk and they give me a sensation unlike that of any of my other heels. I began thinking of ways I could possibly wear them out or to work. I have some concerns about wearing them to work only because my employer likes to write utterly ambiguous employee policy so that management has absolute discretion in enforcing as it sees fit. Likewise, as I have a knack for pointing out gaping holes in company policy, much to the chagrin of my bosses, wearing an item that even remotely approaches the realm of "inappropriate" will potentially cause problems for me. This is why I have yet to wear a mini-skirt to the office although I absolutely have the legs for it! Then I thought, what if a cover my boots? I have a pair of long, wide legs pants that are perfect and would only expose the very bottom of the heel and toe. I personally do not care if anyone sees them as the sensation of wearing something that tall is strictly for me. So, the question is, based on the photograph, would you do it? The photo with the skirt is just to show what the boots look like but the one with the black pants is an actual outfit I might wear. I have several pair of 4"+ boots/heels that I am now reconsidering wear to work when the bosses are not around, such as the friday before long/holiday weekends. I am really inspired by the banker with whom I spoke because until now, wearing over-the-knee boots in a professional seemed so taboo and verboten, especially if one was over 25 years old.

My elder son got married on Thursday. It was a very small wedding. I would estimate the total number of guests at around 30, and about half of those were parents/grandparents. I was the only one in the whole bunch wearing heels except for my ex-wife, who has always been a big fan of heels. To be fair, I don't believe I've ever seen her wear a pair of "high" heels in her life, but she was often in mid-heels when we were married. Thursday she wore tan suede pointy-toed pumps with a three inch block heel. The only other exception was the cellist in the string quartet they hired to provide the music. The cellist had on black patent pumps with a three inch stiletto heel. We'll take what we can get. For the record, I was wearing my black Aldo oxfords with 4 1/4" slim heels. Almost stiletto, but I can't honestly call them stilettos among enthusiasts.

Stuart Whitzman Mary James with a 4” thicker heel. They are comfortable out and about

This is so true! I remember the first few times I wore heels in public. I was so focused on what people might say, or what types of looks I might get, that by the end of it, I was like “wow, no one really even looked, or seemed to care at all, one way or the other”. Psychologically, I think I prepared myself too much, for negative reactions, ridicule, or even dirty looks, and when none of that happened, I realized that the whole event really wasn’t as big of a deal to everyone else, as it may have been to me. It honestly felt like all of the mental preparation and courage I summoned leading up to my finally walking in public wearing heels, was a gigantic nothing burger! In a strange way, It was sort of a let-down, almost making me feel like all of the excitement I had been building up in my own head, along with the thought that others would be ready to laugh, ridicule, point, or whatever, gave the whole thing much more importance than it actually deserved. What I got from my first experiences wearing heels in public, is that most people either, don’t care, or are not paying attention (mainly because they are probably too wrapped up in their own routines and their own distractions). I truly believe more guys would venture out in heels, if they realized that 99.8 of the “barriers” and negative reactions they expect and prepare for, or that they imagine that actually prevents them from experiencing and exploring wearing heels in public, basically come mainly from their own thoughts, and not the public/society itself. As far as reactions go, over decades of wearing heels in public, I’ve gotten maybe three or four dirty looks, maybe double that amount of looks of confusion or “double takes” (like when someone sees something, looks away, then quickly looks back, as if to say, “did I really just see what I thought I saw?), and I should add that many of those were woman, who followed it up with a kind smile! As far as comments, I’ve gotten literally dozens, from males and females alike, mostly all positive! Definitely nothing that would have ever kept me from going back out in heels again, that’s for sure. Bottom line is that most people could care less, and the ones that may notice, are mostly kindhearted people, and not as judgmental as one may think.

Between 85 and 100% of what I wear comes from the woman's side, but other than my heels, I don't look feminine. Even with gel fingernails. More colors and fabrics to play with, better fit.

I hear ya for sure. But, I have found/noticed that a mix of subtle "feminine gear" along with decent "masculine gear" can be a great look indeed. Just a guy, happy to be a guy, wearing a touch of "feminine gear". I find this to be a very confident/powerful look indeed. Needless to say, many guys have nice long/lean/toned builds and look great in even more feminine gear, not a look I can pull off for sure... I recently bought a few pairs of women's nike leggings/work out gear pants from a thrift store, just to get a better idea of what size would work for me, and just how I would look. I enjoy wearing them, but afraid to see an actual picture of me...Afraid I might be "overstepping", writing checks my old dad bod just cant cash!

After four days in a row of practice, I believe I am back to normal. The super cold weather has left us, at least for now, and I can stand to walk outside again. It may be that I will feel like taking some pictures again soon. It's kind of too bad I missed the last couple of weeks. I wore knee high boots to church two weeks in a row!

I realize that I do not need to share the excruciating details of my everyday life on this forum, but I had an encounter this evening that made me wonder if, while out in a pair of heels, we do not notice others who may notice us? A bit of a backfill is needed. My employer mandates that all employees have to exhausted certain types of Acquired Benefit Time (i.e. personal days and/or vacation days) by the end of the calendar year or lose it. As Christmas and New Year's Day fall on Wednesdays this year, about 99% of the staff take extra days off throughout December. I am, unfortunately, that one percent that still has to make my way into the office. As we approached the end of 2024, my bosses began sending emails to their staff indicating on what days they would/would not be in the office over the last two weeks of December. Given that I was the only poor soul who was not taking any time off over the holidays, I decided to make the most of all others being away by designating the last two weeks of the year as "High-high heel days." I decided that I was going to wear those 4+" heels into the office with some outfit that, until very recently, I would never have otherwise considered doing so. I very much wanted to make sure that I was comfortable doing so now so that I could do so again in the future. This past Tuesday, for example, I wore an exquisite knee-length leather skirt with my 4.5" Jessica Simpson - Tulip (model) boots. Today I wore a delicious animal print, just above the knee skirt with 4" wedge boots and a black turtleneck. As a whole, the ensemble was quite haute couture if I do say so myself. After the end of the workday, I headed over to the local wine bar in town as the place has a Friday after work special. After sharing a drink with a friend and colleague from another department that is the monstrosity of my employer, I decided to engage in my favorite, least desirable activity - weekly grocery shopping. FWIW, my colleague raved about my outfit and I told that if she continued, she was going to make me blush, which was not that hard as I was already wearing a nice rose colored blush! As I made my way into the hair care products aisle, I encountered two younger aged women, who I would place in their early 20s. I took notice of one of them because she was wearing very casual, just over-the-knee, 2.5" block, black microfiber heel boots, with distressed jeans. I grabbed some hair conditioner and made my way to the end of the aisle where I encountered the two women. The woman wearing the boots then says to me words along the line of "I love your outfit - you look fabulous!!" "Oh, thank you ever so kindly!!" was my response, which is my standard response and I truly do mean it. The same woman told me that she loved the skirt and I find that making small talk when given a compliment has been received is a means by which to show sincere appreciation of such. I told the women that, in fact, I found it at the local second-hand store, and was amazed to find an item so cute and in my size. Seeing that it fit me so well, I "had" to buy it for the few dollars marked on the price tag. The woman continued to compliment my outfit and then told me that as soon as she noticed me turning into the aisle, she was "checkin' me out." I told her that I honestly did not notice her doing so and again, thanked them both for their kind and encouraging words before heading to the next aisle. In all, I would estimate that I was in the presence of the woman for ~15-20 seconds before she made any compliment to me. Needless to say, it is encounters such as this that I truly enjoy and reinforce my confidence. The fact that I did not notice the woman looking at my outfit made me wonder if, after a certain point of routinely being out in heels, do we drop our guard and not even realize it? Do/can "we" become so confident that over time, we no longer notice who notices us? I suppose one could argue that it is a defence mechanism for any of us to focus on what we are doing when out and about in a pair of heels so that we do not notice others reaction to our presence, if they actually should have one. There have been may posts on this forum regarding whether or not others actually notice "US" when were are out and about while wearing heels. I would venture a guess that the consensus is that no, many others do not notice us when we are wearing our heels and if they do, they care little about such. So, I have to ask if we become like "them" and after a while, take no notice of those who notice us? I can certainly say that I have reached the point where when I am out in heels, I do not notice what anyone's reactions may be as doing what I need to get done is the focus. Thus, if someone should notice me, my reaction is..."And?" The wedges were supremely comfortable but as I had been in them for 12 hours when I finally got home, although my feet and calves were not screaming "uncle" they were tired. I think @Tech will be awarding me "Best Dressed of 2024" any day now!

Well, I guess I feel that not as many folks notice our heels and boots are we once might have feared did notice! Again, I always notice footwear, so mistakenly made the assumption that most others do too. But, on the other hand, I feel that more folks notice than we are aware of. Most folks might notice but don't want to be rude or stare, and they are way too busy to deviate from their immediate missions while out and about. I might not notice folks checking out my boots intentionally, mainly because I want to give them the opportunity to look (hopefully admire) without "being caught looking/staring" by me. Generally, I can usually sense when someone is taking a second look though. For me, I know I am relaxed when out and about, when I almost forget I'm wearing boots.

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

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

Got my first pair of Fernando Berlin boots

About 5 years ago I had a (much) younger woman thank me for wearing heels. She loved heels but had succumb to peer pressure and stop wearing them. Seeing me in heels everyday gave her confidence to again wear her heels. And she was happier. Yes, she liked sitletto pumps.

I have evidently missed my HHP anniversary, but not by much. Evidently, I've been on this site for 12 years! I wonder how this would have all gone without this site. I had already made up my mind that I was going to wear the shoes I liked about six months before I joined here. I'm sure that my fashion life would have been different, but I'm not really sure how. I guess it's been good to know that I'm not the only one, but I've been used to that my entire life, so I don't know that it would have been a deal breaker. One thing I have noticed is that for my anniversary, I no longer have the option to choose a different font than this default sans serif font that I'm not particularly fond of.

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 do not mean to be the center of attention here or dominate this discussion board but lately, that which I have been experiencing has led me to become super confident in wearing heels out and about. I came to this forum many years ago so wanting to wear heels out in public but never believed that I would ever walk out of my residence doing so. Now, I cannot imagine leaving my place not wearing a pair of heels, even if it is to run my garbage to the dumpster, a distance of ~250ft. I was so very inspired by so many posts on this forum to take those steps to accept who I am - a guy to loves to wear heels, and “allow” myself to be seen while wearing them. I looked at many pictures here and was envious of individuals like @CAT because he dressed in the style (and yes, he has it!) I always wanted to do but never thought would be possible. Now, I have outfits the scream style, elegance, and professionalism. And I say this with all the humor in the world, but I hope I am giving him a run for his money! 😍 Over a year’s time, I have gone from being so frightened of being seen in heels to a point where I want the world to see me “en femme,” and I really do not care what others think about it. If someone has an issue of me wearing heels or even flats with a skirt in public, then that is their problem, not mine. I have told those close to me about this – my family, friends, colleagues, and most importantly, my beloved wife of 32 years as of 10/31 (Yes, I was married on Halloween and this year we will be celebrating it in Salem, Massachusetts). I have come to ask the question of, if those who are important to me know about my love of wearing heels and accept it, then from whom and what am I hiding? I am reminded of the line from Dr. Seuss, “Those who mind don’t matter and those who matter don’t mind” How very true. I chose the name “Gigi” based on a few factors. I am a huge hockey fan and some time ago, there was a gentleman from New Brunswick, Canada, named Ghislaine Hebert who was (and I think still is) a referee in the NHL. My wife and I loved that named and agreed that if we ever had a daughter (we are childless by choice) we would name her Ghislaine. I have also always loved the name Genevive and thus, Ghislaine Genevive, or “Gige” was “born.” Gige, however, is not who I am and masks my true identity. That being the case, I want to properly introduce myself to all as I no longer want to hide who and what I am! My real name is Richard and I live just outside of Springfield, Illinois, the state capital; I am a fraud investigator by profession. As some of you know or have deduced, I am originally from Chicago and have a love/hate relationship with that city. I have seen a few other transgender males around my part of the world but they are often much younger than me. I do not approach them as based on solid advice from @mlroseplant, it is probably best not to do so for a multitude of reasons. If, however, someone should approach me and want to talk about or compliment my outfit, I will always make time for them. As much as I love wearing heels, I also love talking about them. If, to the contrary, someone wants to criticize my outfit, then I will be happy to let them know that it takes more courage to be a man wearing heels in public than critiquing those who do. That being the case, if anyone is my neck of the woods or heading up/into Chicago and wants to talk heels somewhere (no strings attached, no obligations, no attempts to “pick-up” anyone – I’m married after all!) let me know as I would be happy to do so. I end with this thought from a meme I saw somewhere…What do you call a man who wears high heels? Answer – a person who want to be happy! Thanks so much to everyone for your stories and inspiration. I could not have ever walked out in public in a pair of heels without them! Photo - another day of catching those trying to "scam the system."

Thank you to all for the wonderful responses - I truly appreciate the support and kind words! As I have made known in several previous responses to other threads, had I not found this forum and read the stories of other men venturing out in heels for the first time, I do not know that I would have ever found the courage to do so myself. Given how far I have come in just about a year, it seems somewhat foolish that I did not do so earlier in my life. As I was driving home from the office in a ridiculously cute outfit I wore today, I was thinking that it is almost a year to the day when I first wore heels (boots, actually) to the office. Although ~95% of the shaft and heel were covered by long pants, I was still so nervous about doing so, and that someone would "see" my footwear and take note of what I was wearing. Then, after my work day was done, I headed out for a quick haircut and as I was waiting in the salon/barbershop, store, I was so nervous my hands were sweating. When my name was called, it was a "here goes nothing...!" moment. I was not ready to have anyone see me wearing heels at that time but, admittedly, it was a thrill knowing that I was "secretly" doing so. Now, a year later, I could not possibly care less what anyone may think as so many people, at the office and in public settings have seen me in heels, that it has become routine. I do not consider myself to be "Superman" or the like when comes to wearing heels out in public but I realize that if someone has an issue with it, oh well...not my problem. I truly do not know why I have so quickly overcome my fears of wearing heels in public. I think that once the first few times were "under my belt," so to speak, it just became easier and easier to do. Not to sound like a broken record but the words of Dr. Seuss have truly taken on a new meaning for me..."Those that mind don't matter and those that matter don't mind." Well, enough of my rambling...Thanks again to everyone! Richard Photo - the aforementioned "ridiculously cute" outfit for work today!

November's entries - I think I wore the orange turtleneck outfit to work...definitely wore the red/maroon dress to the office!

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.

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.

As we all know, there is a “first time” for all events in life that are certainly worth remembering for one reason or another. Over this past Halloween, I had one such event that covered two firsts for me – traveling in heels and being “out and about” in heels with my wife, both of which were delightful. This is just a short recap of both as I believe that they are worth celebrating and/or remembering. On the day before Halloween, I was to meet my wife in Boston for a long weekend to celebrate our wedding anniversary and tour a city that, despite our worldly travels over the years, we had not yet visited. I was to depart from St. Louis while she was to depart from Amsterdam and we would meet each other at Logan Airport in Boston. For this leg of the journey, I sported a simple Anne Klein - 3” heel, black ankle boot. Admittedly, I was feeling a few nerves as I entered the terminal as I reasoned that this was the most crowded place to date in which I wore heels. Regardless, all went smoothly from entry to departure. As the flight neared Boston, I noticed that I was starting to become a bit anxious because of the fact that when my wife would actually see me, it would be the first time she would do so in “real-life,” not just from a picture. Thus, I was unsure if her reaction would be different or not. Nonetheless, we were happy to be reunited and headed to our hotel. There, I eventually changed into jeans and my trainers as we headed out to dinner. The next day (Halloween) we spent walking parts of Boston’s 2.5 mile long Freedom Trail and I am glad I did so in my trainers! For the evening, we headed to Salem, Massachusetts (site of the infamous witch trials in the late 17th century) but as we were heading there via public transportation, we both decided to start the trek in our trainers and change footwear while en route. I had selected my 4” Giaro, pointed-toe, black wedge boots as the choice for the event. Just before arrival at the town's train station, I switched footwear and then we headed out to join the festive environment that it was (think Mardi Gras). After our celebratory dinner, we strolled the town’s streets and as we stopped to speak with a local craft vender, a young Asian woman noticed me. Although I do not remember her specific words, they were along the lines of “You’re a fashion icon” and insisted that I pose for a picture with her. Not a problem as I am always happy to do so. About an hour later, however, the boots had to come off not because of my feet hurting but due to the fact that my thighs and calves were aching from the afternoon walk around Boston and walking in heels was not doing them any favors. Friday did not see me in boots/heels at all and Saturday, I was wearing flat heeled, black microfiber just over-the-knee boots as we visited a friend for dinner outside of Boston. As Saturday’s boots were flat, I will not go into details of those, although the outfit was rather attractive! Sunday morning saw us visiting one last historical sight and a final shopping excursion before heading to the airport for our flight to St. Louis. The plan was to spend the morning activities in my trainers and then switch into a pair of Naturalizer, black leather, 2.5” knee high boots for the trip back to my part of the world. Unfortunately, we arrived back at our hotel later that expected and due to some “issues” of another pushy tour group, departed for the airport a bit later than we hoped. So, once we arrived at Logan Airport, I quickly changed into my boots and made our way to the gate. The “problem” with the boots I was wearing was that this was their initial outing and they were rather tight, especially the left foot. I have a great leather softening spray I use (purchased on Amazon) to help with the breaking in process but as I left this back at my place, I just had to deal with it. I decided to see if walking around the airport would help loosen them up a bit, so I took a stroll around to other gates and as I did so, a young woman with body piercing just about everywhere possible commented that my outfit was “sensational!” I profusely thanked her for comments and headed back towards my departure gate, taking the long way back so that I could “strut my stuff” and everyone in the terminal could see me – boy did that feel great! Overall, the new boots were not “too” bad but by the time I actually was enroute back to my place, the left boot had to come off as it was very much pushing against my swollen foot. As I write this, I have sprayed the boot with the leather softener and I am wearing it with multiple pairs of thick socks to help stretch it out a bit. At St. Louis - In Salem (MA - no "real" witches found!) At Logan (Boston) Airport

I have two things to report. Number One, I talked with a college friend of mine and told her that I was wearing my giant Prada mules for my morning constitutional on account of the fact that it was raining. I know I shouldn't abuse such expensive shoes in this way, but hey, they keep my feet out of the puddles. I didn't pay anywhere near the grand that this brand normally goes for brand new. For one thing, they're slightly damaged, and that was before I started using them for rain shoes. This particular friend is not in my true inner circle, so she said the usual "I want to see pictures, or it didn't happen." Number Two, the other picture you see here is my church OOTW. I got my new pants to go with my new shoes. This is one of the few times, maybe the ONLY time I've ever worn the same pair of shoes to church two weeks in a row. To refresh present recollection, they are Steve Madden Daisie pumps in mauve. They're just a tad under 4 1/2", which puts them more in the 11 cm range, but hey, I can walk in them!

Which reminds me that Whitby (on coast of North Yorkshire, for those unfamiliar) is known for its 'Goth' atmosphere, mainly due to the Dracula legend. And there are Goth weekend events on 1 - 3 November, doubtless following-in from Halloween. Even when these events are not on, Whitby is a popular place for people in Goth clothing, which will surely include some extreme heeled footwear, with long points, buckles etc.

Here I am with another church OOTW. The only notable thing here is my new shoes is the color, which I cannot define. The camera actually captured the color fairly accurately, it's a sort of purple, but it's not really purple. Anyway, like most of my Steve Madden pumps, I can wear these things just fine. They're not really all that high, coming in at 4 3/8 inches.

Earlier today I had an encounter with a woman in heeled boots that was so unexpected and amazing that I felt the need to regale all members of such. So, if you are interested in reading about it, then continue on but if not….well, too bad. Today was the quintessential autumn day in central Illinois as the high temperature was ever so slightly above normal. It was brilliantly sunny with not a single cloud in the sky and at this latitude, it is the peak of Autumn colors. Given such, it was not a day to spend indoors in any capacity and it was my desire to be outdoors that led to an inspiring encounter that will be long remembered. The dialog of the conversation is presented as the best as I remember it. After completing a few errands in the morning, I returned home to drop off my purchases and have a light lunch. The day was simply too beautiful not to enjoy the autumn colors and thus, I decided to head to the Lincoln Memorial Gardens located on the east side of town. The Memorial Gardens is a 125 acre large nature preserve and probably the best place to stroll along marked trails on this marvelous day; the entrance is about a 20 minute drive from residence. En route, I came upon a non-descript intersection controlled by a traffic light and as I had the green, I approached without much caution. There is a small petrol station on the northeast corner of such and as I neared it, I could not believe what I observed – a woman wearing five-inch, black stiletto knee high boots stepping out of her vehicle. As soon as I saw her, I thought to myself, “Did I just see that?!” I immediately turned into the gas station and pulled my car to the pump behind and on the other side of her car. I could easily see that yes, she WAS wearing the boots I thought she was wearing! Although I could have used a bit of petrol, I was not going to purchase it there as the station only offered the lowest octane regular or diesel. Sorry, but neither one of those are going to work for me. Upon stepping out of my car, I reached for the window washing brush and cleaned up the rear window (it was actually rather dirty) and then grabbed a few paper towels the clean the edges and wipe away the streaking. As I went to place the paper towels in the trash, I cautiously approached her. “Excuse me, ma’am” I stated. She looked at me and then I said, “Those are killer boots!” A bright smile came across her face and she responded, “Oh, Thank you!!” I then professed that her boots were those which I would love to have in my closet. As she seemed to be delighted with the compliments, I asked her about the brand she was wearing. She leaned against her car and raised her left foot so that the sole and heel were facing upwards. I could see that the boots fit her calves like a glove. “I don’t remember where I got them…Oh, they’re Nine West. So it’s a decent brand” she stated. “Yes, Nine West has great designs – I have a few pairs in my wardrobe” I replied. “I do not mean to be forward” I continued, “but you look sensational! Are you attending an event?" I asked. The woman, probably in her mid-40s, and an “average” physique, was wearing a black dress with a hemline that hit about mid thigh, with a slightly below the waist length black jacket. She had long, straight brunette hair coming to about her mid-back, and a tongue, nose, and just below the lower lip piercings. Based on her appearance, I though she may be heading to a Halloween party. Her outfit is hardly that worn around my part of the world. “I just left a funeral” she replied. Talk about awkward – complimenting a woman on what she is wearing to a funeral… “Oh, I am sorry to hear that” was the best I could do. “Regardless, your outfit is stunning” I said. “I don’t mean to be rude by complimenting you, but your outfit is incredible!” I continued. I do not remember her exact response, but she mentioned that she loved the compliments and never tires of hearing such when directed her way. Not wanting to make her feel that I was wanting to do more than simply express my appreciation for what she was wearing, I started moving back towards my car. “Have a wonderful afternoon” I said. “Thank you darling! You’re beautiful!” she said as got back into my vehicle. From there, I left the premises with someone needing to pour cold water on me! As I drove to my destination, my mind was racing. Wearing five inch stiletto boots in a funeral? That is extreme confidence in my eyes and has so inspired me to step up “my game.” During my lovely stroll around the Gardens, I made a vow to do something that I have wanted to do for years. I will reveal such, however, when it comes to fruition. The picture of the boots were not the exact model she was wearing, but were fairly close. When I should pass away, I want those in attendance at my funeral to wear the same outfit.

Forget the end of the year holidays and all that about being the "...most wonderful time of the year" nonsense. This is it - the start of boot season! So, this morning was an appointment with my dentist and this was the outfit I wore (never hurts to make a memorable 1st impression!). Do not get me wrong, I am already looking forward to the return of my warm season heels, but given the choice, I would always select boots over pumps as the former just seems to fit better. Unfortunately, today was just a preview as the weather will warm over the next few days making boots (and tights) a bit "too" warm. And the outfit with the orange skirt was the end of summer clothing day on 9/30.

Funny you should ask, I have told my GF of 12 years the exact same thing, "You have it you should flaunt it" She says I leave that up to you! Shes usually a size 4 and 7 shoe, looks incredible in everything, BUT does not want to be the center of attention,,,,,Well I DO! She really wonders how I do it. I will say that my travels back and forth constantly from Chicago to Tampa I am always dressed up. I am in 4- 5" heels 99% of the time with a dress, skirt/shirt, Lulu Align or Groove pants used as dress pants. I did wear on my last trip down a Lulu Align skirt with a Lulu Define jacket and some Nike gym shoes, felt kinda weird to not be in heels but it was a great looking outfit, I thought, even went straight out to dinner when I arrived. We were commenting on boot season earlier and I will be out and about this weekend with a new pair of knee boots or otk boots. I have bought a few pairs of ankle to otk boots already this year. Back to the topic, I love to get an outfit put together and go out for an afternoon or evening. My GF says when it comes to the clothes/outfit and heels I am more of a chick then she is!!! Not sure if that is good or bad but I will take it as a compliment. Most of you know I could care less what people think or say, most people don't even notice. I wear what I like period. I wish it was easier to post pics here but it is a pain in the a**. Come to Chicago and I am sure we can cross paths somewhere! I'm not here for a long time, I am here for a good time!

I’m at the Copenhagen airport. Nothing but sneakers and the odd pair of crocs. I did see a woman wearing OTK boots on the Metro but with ordinary heels stop the presses - someone wearing heels! On my flight! And it’s a guy in a very nice, quite feminine pair of ankle boots with 3” heels not at all hidden. Otherwise dress just as a well dressed smart casual guy. I believe it’s the first time I’ve seen a guy in heels out and about

Found myself in an interesting conversation this morning in my hotel. I am leading a tour group at the moment and someone was talking about achilles tendon problems. A woman, one of our guests, spoke up and said, matter of factly 'Men can't do this of course, but women can wear heels to ease the strain on the tendon." To which I replied, just as matter of factly: "Men can do that." She gave a start and spluttered, "Well ... I ... I ... suppose they could ..." I left it at that.

So, I thought an update may be necessary. Probably not though.... I have been giving much thought to this topic and have fielded and read a few words of well spoken advice. Thus, I have arrived at the conclusion that heel height is not always that important. I have come to believe, in fact, that what is important is not so much what is worn but how it is worn. I would argue that one can appear equally as elegant in flats as a pair of 5"/12cm heels. Take today's outfit for example. I was wearing a maroon turtleneck, khaki dress pants, and brown Miz Mooz (brand) 3.5" heeled oxfords. The colors matched perfectly and I accented the outfit with a warm colored short scarf, 15mm rose gold hoop earrings, and a brown belt. Overall, I thought the outfit was gorgeous and reflected a sense of elevated style - simple but well matched pieces. Compare this to the previous day's outfit which consisted of a black/grey/white color block long sleeve shirt, a knee length black skirt (BTW - my first time wearing a skirt to the office!) and a wonderful pair of almond toe, black knee high harness boots with a 1" heel. Again, simple but well coordinated pieces. Although the two outfits were very different in tone and appearance, they both displayed a sophisticated and professional style. I felt equally comfortable in both. Tomorrow evening I am attending a small reception for the opening of an art exhibit for which I will be wearing a black/white sweater, black pants, and black leather loafers, along with a black Spanish Beret (made in Spain but found and purchased in Ghent last April). Once again, simple and elegant. I suppose the point to all of this is that, although heels are wonderful and I will continue to wear them as often as possible, one does not always need to wear the highest heel possible in order to display a sense of style, class, and elegance should that be the desired look. One can have great style in very low heels (e.g. kitten heels) or even flats provided that the outfit with which they are worn is of the same caliber. To me, I believe classic styling of shoe/boot and outfit has always spoke loudly about a person as much as current trends; classic styling will never go out of style as far as I am concerned. Thus, low heels can be just as alluring as a 5"/12cm stiletto; black kitten heel pumps/slingbacks will always be supremely elegant regardless of how tastes and styles change or fade. If I had to provide an example of such, I would say look no further than Kate Middleton (or Jackie Kennedy) as she can make flip-flops or house slippers elegant. So, in essence, the height of the heel is not as important when compared to how it is worn. Flat is not necessarily boring and very high is not necessarily "trashy."

Been public for many years and even at work. I'm not even queen as you put it. I love my heels, love how they feel and love how they look. I wear nothing less the 5 inch mostly stilettos yet everyone knows I'm masculine. Women have told me it takes balls, but I'm old enough to remember when if a guy wore an ear ring he was considered queen. Now women have tattoos and brush cuts so why should I not wear heels.

A very simple, but true story. Attending a conference with my coworkers, I wanted to make a statement with my professional attire. I decided to wear my prized Christian Louboutin Hot Wave heels, the iconic peep-toe Hot Chick. Knowing the allure these shoes hold, I aimed to turn heads. As I sat in the lobby of the Marriott Marquis, I dangled my foot, arching it just right to create an enticing display. Many men glanced my way (dozens), but one in particular stood out. In a rush, he excitedly pointed at my shoes and exclaimed, “I have them too!” He quickly flashed his own red-bottom dress shoes, also by Louboutin, before tripping over himself and hurrying off. Later that evening, during the inevitable happy hour, I was still rocking my 130mm Hot Waves. Seated at the bar, enjoying a bourbon, I crossed my legs to showcase the heels. Off to the side, a man was staring intently, clearly captivated. I continued to flaunt the shoes, emphasizing the arch and silhouette of the 130mm heel. He was so distracted that he barely paid attention to his colleagues. Before leaving with his group, he approached me and said, “Nice Hot Chicks.” Though he got the name slightly wrong, it was clear he was enamored with the shoes. Unfortunately, it was a missed connection. I never saw him again and have no idea who he might be. Yet, with his evident interest in these rare heels, I suspect he frequents the same communities and forums as I do (HHPlace, Reddit, etc.).

Very presentable - one looks at the photo and sees at first only a well dressed man. The fact that he’s wearing heels is only a secondary observation - one that could easily be overlooked in passing. The heels aren’t hidden, they appear natural and in a way that can go a long way towards normalising the notion of a man in heels. I can imagine the trouble with the pant legs getting caught in the back of the shoes. Ankle boots would indeed be a good idea in those circumstances

Sounds like a nice day out! Yes block heel ankle boots and knee boots seem much in fashion - fine by me as I like the style. I just wish that given their popularity they’d be made in larger sizes! I see knee boots quite often up here in rural Yorkshire but they are generally gum boots or riding boots and always worn only by women. I am the exception - I might not be able or willing to wear heels in the rough and muddy towpaths, but my low heeled knee boots are always the nicest. I am getting known as the guy who always wears tall boots.

I'll second that - and for the same reasons. Platforms spoil the elegance of high heels and often do indeed look clownish

I ran across an Instagram post the other day which was a split screen of a model's feet. On one half, the model was wearing what looked to be 4 inch stiletto sandals. On the other half, the model was wearing 4 inch block heels with a mild platform, less than an inch. The caption read something to the effect of, "Which one is more likely to cause you to sprain your ankle?" I have yet to answer one of these kinds of things, even though I want to. I didn't reply to this for two reasons: 1) I was on my phone, and didn't feel like typing out a long reply, which is what it would take. 2) The post was already 3 weeks old, and had probably 500+ replies. I don't need to waste my time for that. My answer, of course, would be, "It depends." For most situations I am in, however, the single sole stiletto is more my friend, though I can't say that I'm worried about spraining my ankle in any case. I wear platforms all the time out in the wild, and it's absolutely true that if you step on a pebble or a twig in platforms, it's going to apply a lot of unwelcome sideways force to the ankle, a force that would be much less in single soles, regardless of heel configuration.