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Hi all, After a long time of meaning to post but never executing, I thought I'd just start a new threat to document my adventures in heels. Nothing complicated, so dont expect wonders, but just sharing pictures and this and that. Our neighborhood is pretty progressive, and over the years, they've gotten to know me in heels. This past week, we had some cooler weather at first, so my wife and I were at the local brewery in booties: That said, boot season is pretty much over in this part of Texas, and towards the middle of the week it was already sandals weather again, so we wore these beauties from Jessica Simpson. Clearly, I need to work on a better angle, but I don't like making a scene taking pictures, so under the table / bar snapshots are mostly what happens... Case in point, this was yesterday's choice.

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.

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.).

Several interesting events happen this week. On Wednesday I stopped at the Post Office on the way into work. As I past a woman getting to her door she stopped and told "I just love those boots" (Impo boots with 3.8+" skinny heels) "I wish I could walk as well as you in them." That's just normal for me. It's what happen on the way out that makes this an event. When I was about 11 meters from my car, I felt something wrong...looked down and the platform had separated from the top of the shoe. Got to my car, took off the boot and drove home. Lucky, I was only 4 miles from home. Went home and changed into my Jessica Simpson faux suede knee highs. I have since glued the shoe together. I wonder how many miles I have logged in those shoes over the last 6 + years; 50?, 100?, 200? Today, was a meetings day, again had the JS knee highs (rainy/windy day). After one meeting, a woman told me she always likes walking behind me because she likes the heels I wear. We discussed shoes for a few minutes, she and another woman were fans of JS shoes. Sheepishly she confessed that she owned over 50 heels, I told her "that's ALL, I have around 100." We laughed.

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.

Thought I would share this post about a very old pair of Pleaser ankle strap pumps that I have finally decided must be put out to pasture. I couldn't say how many miles I've worn these amazingly comfortable 5 inch heels, talking Melroseplant level I'm guessing. I've re-heeled these at least 6 times. Finally blew out the sole and upper part of the vamps this last week. Surprisingly they are still easy to walk in and sturdy but still long past any visual appeal. I think these definitely paid themselves off many times.

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.

Just purchased these for an insanely low price, £1.75 brand new. Was such an amazing bargain, would have been crazy not to. Theyre the Stessy from Aldo. Im just not sure what to wear with them 🤔 🤣

There’s a men’s fashion Instagram account that keeps popping up in my feed and it’s rather interesting. Yesterday they had a post about men’s fashions becoming more feminine - specifically mentioning skinny jeans. The chap whose account it’s, and who deals in bespoke suits, was very much against this. I posted a comment saying that I thought it was time to lighten up, allow men the same degree of freedom, fun and theatricality women took for granted. I was pleasantly surprised to have 75 (and counting) likes and only one (polite) disagreement

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 have been thinking about this post for a while and promise to try and keep it on point. When I started wearing heels, the height of the heel was what was important – the higher the better and I always went for 4.5” – 5.” The style of the heel did not matter whether it was a stiletto, block, wedge, or some other form. I loved such high heels because there was a certain irresistible and indescribable feeling of just being able to walk on a heel that I found to be so horribly alluring. Fast forward to November 2023 when I started wearing heels out in public. I started with 4” block heels in order to get comfortable with doing so and to date, have only worn a higher heel out to an event just once. When I started wearing heels to work earlier this year, 3” – 3.5” seemed to be a good start but for me, 4” is the limit for my own personal reasons (do not want to restart the what is/is not work appropriate debate). I have always felt that I wanted that which I was wearing to compliment the heels I chose for the day. I never felt comfortable wearing “guy” clothing with heels and as a result, began wearing feminine clothing with any pair of heels while out in public. To me, and speaking only for myself and not to offend anyone, most heels are alluring but “guy” clothes are boring and drab, thus, the two types of clothing are not compatible for my tastes. As I realized that my style of clothing to wear with my heels was starting to take shape, I began shopping for heels that matched the outfit in terms of color, style, and practicality; heel height became secondary. Thus, the height of the heel started not to matter so much anymore. Not to get off-topic, I will wear “guy” lounging clothes around my place when I have a new part of heels that need a bit of “breaking in” time before they are worn out in public. Soon, I began to feel a sense of comfort and fulfillment in the entire outfit even if I was only wearing kitten heels provided that what I was wearing with them reflected my sense of ‘haute couture.’ I, for example, love the look of tailored wide-leg pants with either a kitten heel or a shorter heeled animal print pump. Such reflects a certain sophisticated and classic elegance, a ‘je na sais quoi’ about it. The summers in my part of the world, however, can be quite unforgiving on some days which wreaks havoc on my feet; heels that fit today will not fit tomorrow if it is hot and humid. Fun and useless fact – one acre of corn stalks releases 2-3k gallons of water vapor (humidity) when they are short of maturity. When the heat takes hold, I opt for my Vans as I have several pairs in many colors which allow me to easily match those shoes to either my pants/skirt or top. Likewise, I have a very comfortable pair of loafers that are probably one of the most comfortable pairs of non-trainers I own. When I go this route of shoe choice, I still feel as great as I do when I am wearing a pair of heels out in public provided that the outfit looks great and my accessories match. Thus, I have come to realize that as much as heels are an expression of whom I am, I can still do so without having to wear 5” stilettos or the like. So, I have to ask if the height of the heel really matters?

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.

There were some responses to various threads on which I wanted to comment but, admittedly, I am too lazy to go back and try and find them. Thus, I going to throw out a melange of thoughts here - think of it as High Heel goulash. First, someone had mentioned the idea of more men wanting to wear heels in public but for reasons unknown, do not do so. For a time, I was an assistant administrator of a group promoting men wearing high heels in public on a different social media platform. I happened to notice a few trends worthy of discussion based solely on my observations, and not on research or scientific data. It appears that the number of men who actually wear heels in public is but a very small percent of those who want to do so. It seems that fear over some sort of negative reaction, consequence, or the expectation of "men being men" was the greatest hurdle to doing so. This is completely understandably as the idea of men wearing heels or dressing "en femme" is still taboo and may always be to some. Although I could not make any sort of reasonable estimation, I would believe it is fair to say there are a fair number of men out there who will forever hold a secret desire to wear heels out in public but the fear of reaction to such prevents them from doing so. One of the reasons I stepped away from this group was due to the fact that, although it was created with the purpose of getting society to accept men wearing high heels, very few of the contributions to it were of men wearing heels in public. I came to believe that many of the members held a deep fantasy of wanting to wear heels in public and this was as close as they could get to doing so. Next, I seem to recall a thread somewhere about whether the excitement of wearing heels in public fades after a while. I given this a lot of thought and my answer is "Yes" and "No." My wearing heels of any height in public is now my norm, so yes, the thrill of doing so has faded to some degree. There are still times when it is exciting such as when I am wearing a new style of heels or outfit. Recently, I started wearing open-toe heels (and Espadrilles) in both public and to work, and it was exciting the first few instances of such as I believed that I would never do so. Now that we are heading into the autumn and the cooler weather, boot weather will soon be here and I am excited to finally be able to wear a skirt to the office (As previously noted, my office is so over air conditioned, heavy clothes are required in the summer to remain warm and thus, my summer skirts are "too thin" to be worn there). So, I suppose it is fair to say that the thrill of wearing heels in public does diminish when it becomes the "norm" or is, in fact, expected. For me, however, the thrill of wearing heels in public is still exciting because before I head out to wherever, I take a look at myself in the mirror and love what I see. Likewise, I park my car at the farthest end of my building's parking lot and at the end of my work day as I head to my vehicle, I see my reflect in the other cars I pass along en route. Simply seeing my outfit or even knowing that it is "cute" still develops a tremendous emotional charge for me. I adore the look of wide leg pants pair with a pair of kitten heels and knowing that I am wearing such is an addictive rush. Also, when I receive a compliment on either my outfit as a whole or even part of it, it makes it all worthwhile. Finally, somewhere a member had posted a response about Hunter rain boots. Do not get me wrong, I have the greatest appreciation for knee high rain boots and appreciate their practicality. I, however, would only wear them as a means to keep my feet dry when it is wet outside and to prevent me from destroying a pair of heels by having to navigate around puddles of standing water. Well, sometime ago I saw these and when they went on sale, jumped on getting a pair - style and practicality all in one!

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

I finally plucked up the courage to go out in public in heels. I wore a pair of black patent Mary Jane's with 3 inch block heels to walk to my local convenience store. There were maybe 2 or 3 other customers there, I just grabbed what I needed, paid and left. I don't know if nobody noticed but no-one said or did anything. I was amazed how easy it was.

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.

Thanks! Can't wait to go! Super excited! Thanks! Can't wait to go! It's a place that my wife and I have wanted to visit for quite some time - super excited to finally being able to do so!

I too have been thinking how nice it is to see a topic near the bottom of the board take off - and such a good topic too, so germane to the overall tenor of the site! As to feminizing the male wardrobe, I have taken a step I’d never thought I would take and have bought myself a skirt - a midi pencil skirt. Here I need to give credit to @CAT for being a positive influence with his outfits, although our tastes are very different. I’ve always liked the look of long skirts paired with tall boots and have increasingly wanted to have something other than skinny jeans with which to pair mine. And so I decided to give it a try - and also to experience the novelty of wearing a skirt, something I’d never tried. in short, I love it. In fact I’m surprised by how much I like it and even more how natural it feels wearing it. Again, it’s a longer skirt, down to my calves which is something that suits me. I’ve never been a fan of mini skirts and have no desire to wear or try one - it’s just not me, and not because I’m being self conscious. The midi pencil skirt though very much is me - surprisingly so. I feel very comfortable wearing it, physically and emotionally. And it works really well with my boots. I can definitely see myself acquiring more of these skirts. I really like them.

This post was truly inspired by @Mr. X's recent post regarding the wearing of heels while playing a drum set. As I have also done such in the past and did not want to get weighted down in the minute and boredom of the technique in doing so, I decided to spin off a new thread as his post revived a 1/2 unpleasant memory of attending an event which involved heels many, many years ago. July 15, 1989, was somewhat of an unusual Saturday night as I and my then next-door neighbor travelled across the Chicago metro area to attend a concert by the Prince of Darkness, Ozzy Osbourne. He was touring in support of No Rest for the Wicked, his first album with his newest axe grinder, Zakk Wydle, and we had fourth row seats. Most unfortunately, there were two opening acts through which we had to suffer before Ozzy et.al. hit the stage. One of those acts was White Lion, a band who then, as they and the whole ‘hair-metal’ genre of the 80’s continue to do, fill an area of a needed void. The first act to take the stage was a four-piece, female, glam outfit who called themselves Vixen. Although their music should be forgotten and they reflected just about all that was “wrong” with the ‘hair metal’ scene of the time, which is everything, to two late teenaged guys, they were gorgeous and we did not want to miss their set only for this reason! That night, all of them wore skin-tight clothing and heels, and had hair that extended several feet in the air, held in place by several gallons of hair spray. Being that close to their heels was the only aspect of their show that was tolerable in any capacity. Vixen had a video that received somewhat regular airtime on the difficult and frustrating to watch MTV’s mistitled Headbanger’s Ball (To the European members, think Eurovision but somehow, far worse) on Saturday Nights. The song was entitled Edge of a Broken Heart and although completely laughable by today’s standards, I went back and watched it on Youtube the other day. Although all of the members of the group are wearing tall heels in the video, it was interesting to see how the style of such has changed from the late 80s to today. This compelled me to think about how heel styles have changed over the years and who was at the forefront of such. Clearly, one can identify those individuals or television shows where the fashion du jour was on full display. That which I find to be amazing is the fact that although the idea of high heels essentially remains unchanged over the past few decades, designers can continually find new ways to change the physical design from year-to-year. Thus, it may be easy to place any pair of heels in the decade in which they may have been worn without any clues beyond the heels themselves. It truly stinks, to put it mildly, to know that some styles of heels have a life-style span of a season or two before they are considered to be “dated.” This, I think, is why I learn towards classical styles as what is trendy now will not be so next year and timeless styles are just that – timeless. I would rather have and wear a pair of heels that hail from Jackie Kennedy’s time than from last year as classic styling never goes out of style. The idea of short-lived footwear trends can be represented in a pair of boots I have – ‘Tulip’ (model) from Jessica Simpson. They feature a 5” heel with a ½” platform but the top has a fold-over flap which was the style about 10 years ago. When I wear these boots, I take that flap and fold it into the actual shaft for a more contemporary look or unfold it to give them an over-the-knee look. As for the show itself – Ozzy, as expected, ROCKED! Zakk covered all of the Sabbath songs very well and played those incredible solos performed by the late and great Randy Rhodes note for note. Sadly, however, it was the second time I had to endure the craptacular show of White Lion, who I witnessed open for AC/DC the previous September. The best part of their set was when it ended and the road crew moved their gear out of the way for the main act. Here is a picture of Vixen. If you should watch the video on Youtube, I highly recommend you do so with the mute on so as not to damage your hearing by simply listening to the song (if you could make it all the way to the end).

Yeah...I know I'm breaking the rules here, but this outfit was just "too cute" not to share....My leather skirt and 4.5" Jessica Simpson "Tulip" boots. Although I adore these boots and I bought them unworn, the interior lining is quickly deteriorating due to their age (maybe 10+ years?). I have already started planning out their replacement. Regardless, what a thrill it was to wear such high heels to work. Received several compliments in the ensemble as a whole!

My favorite work boots are my Jessica Simpson suede knee high stilettos. But then all I do is talk, write, think, and go to meetings. I know, it's a tough life, but someone has to do it.

I remember over a decade ago when I switched to only women's shoes and got my first booties with 2 inch heels. The hardest thing was getting use to the click. BUT I'm in the too "old-to-care" group, buy and wear what I want. I just got a cheetah vest, so soft, and already wore it to a company holiday party with my 3.5 inch thin-heeled knee highs. Both the vest and heels got random compliments. I also like wearing short-shorts and sitettos knee highs in the summer, just for the mind blowing effects of it. I like my pleather skirt with knee highs. LOL

Yes you do a very good job of putting things together. With my ensemble of boots, jeans and jumper there is little room for your style of creativity. I could never do the leather miniskirt - although I admit that the other day I noticed an ad for a leather midi pencil skirt, calf length, that did pique my interest, something I could at least imagine with my OTK black suede boots

At this point in my heeling career, I have a more subtle struggle when it comes to confidence. Now that it is winter, I basically don't have any confidence issues at all. Long pants and heavy coats cover up a multitude of sins. In the summer, however, short shorts and open toed mules expose your every fault. I went through a period a decade ago when I never wore shorts at all, because I felt I would get too much attention. I can't really blame myself, because I think even a cis-woman wearing shorts and very high heels would attract attention, perhaps unwanted. To address Pebbles's point, I did a lot of walking during those first years in what we would consider modest heels. I don't think I necessarily went about it in a very efficient way, because I think I still looked awkward, having no coach or advisor to say, "You look like a clown*." What it did, though, is allowed me to find my feet, literally, and learn how to navigate the real world in heels without fear of actually falling down. I never would have thought, for instance, that stopping at a crosswalk after walking at a pretty good clip for several minutes, would be hard. Maybe it isn't for some people, but I found that coming to a sudden stop after walking was difficult to do gracefully, as I was struggling to keep my balance standing perfectly still. * Come to think of it my wife did, but was unwilling to offer any constructive criticism.

Great topic! Although my interest in feminine boots stemmed from a liking of go-go boots, I’ve always been partial to boots over shoes and with the exception of my cycling or running shoes, I only ever wear boots - and gave done since adolescence, growing up in the mountains. I lived in hiking boots through university, where I studied geology and archaeology, and my choice of career has allowed me to continue in the same vein. I’ve no neckties but plenty of pairs of boots. My oldest pair, and still much in use, is a pair of Scarpa mountaineering boots, made of a very tough suede with heavy Vibram soles. Been to Antarctica many times - warm and sturdy and although now 25 years old are still going strong with plenty of use left in them. I still wear them occasionally on the towpath. I’ve a pair of De Walt steel capped work boots as sometimes I land assignments where safety footwear is mandatory.they are all right, not uncomfortable if worn with thick socks, and pass muster when I need to get access to industrial sites. I e several pair of knee-high biker or engineering boots from Jean Gaborit which I absolutely love. My present go-to boot is their Kansas patrol boot in heavy black leather which has seen much service over the past year (and looks it - I need to buff them up) I’ve a pair of their chocolate brown knee high Vezin engineering boots which I also love. They are the most comfortable boots I’ve ever owned and would wear them more except they are so hard to get off. Getting them on is easy - a bit if a push - but removing them is hard. While they are on they are wonderful comfortable. I had an assignment once where I was pretty much in my feet for 36 hours and wore these the entire time without the least discomfort. Since I often wear heels while writing or editing, I suppose I could call those work boots too, but I shall stick with these! ,

Do we get "retro month" entries? That is, if I missed submitting an entry in, say, July for example, can I submit an entry now for that month? I ask because I wore this super cute outfit to the office and after the day was done, I went to the Ulta (cosmetics) store for a few products. While there, just about every woman in the store complimented me on my outfit and needless to say, it was quite flattering.

Nice! It just so happens that I have two pairs of this style of ankle boots, both from Schutz, and why I have two pairs is beyond me (can you say "impulse buy" on the second pair?). Both are ~4" in height and I wear them with long boot-cut jeans for an rough but elegant look. Oh and forgot to add, yes, I will be wearing these to work in the next few days!

Ever since I got my scooter, I decided I needed some sh*tkicker motorcycle boots. I got these Steve Madden Laurie boots last summer that fit the bill. In fact, perhaps they fit the bill a little too much. I bought these on Poshmark for $25, and you know how sometimes things look different when you see them in person. It's my own fault, of course, for failing to notice that these boots sport HUGE, HONKING TWO INCH THICK HEELS! I mean, I do have some chunky heels in my collection, but these take the cake by quite a bit. I think the heels on my second chunkiest pair are a mere 1 1/4" wide. I did not wear these boots on my motorbike trip last summer because I received them only one week before the trip, and as y'all know, that would be just plain foolishness to wear them on a long trip, unvetted. I did not really get around to vetting them until a few days ago. Specs on the boots are: 4 3/8 inch heel height, 2 inch heel width, 3/4 inch platform. Here's where the math lies a bit: The math says that the boots are 3 5/8" effective heel height. The first time I wore them, I thought, "These feel quite a bit higher than 3 5/8. More like 4." Upon closer investigation, they are more like 4 inches because of the way the footbed is designed. At the front, the footbed is pretty much even with the top of the platform. In other words, there is no hidden platform at all. At the back, the inner footbed is substantially higher than the top of the heel. Almost like there's a little mini lift in an already high heeled shoe. Weird. Mystery solved. They really are 4 inch heels. Before last week, I had worn them a couple of times to ride, but hadn't really done any substantial walking in them. I found them to be rather on the tight side, so I thought that I needed to actually do some walking in them, just so I know what I have. What I found was rather surprising. I took a route such that if something was badly wrong, I could cut the walk short without having to struggle too much. What actually happened was that I wound up walking a full 2.2 miles in full comfort. It seems the boots had already stretched out quite a little bit withing the 2 miles. The other surprising thing is that they don't feel all that clunky when walking, as many shoes with giant heels do. They are almost graceful. Almost. I figured I'd look and feel like Frankenstein's monster, but I did not. Hopefully, they hold together for a while. I have found that tough-looking, clunky shoes often fall apart quickly. 'Cause you know that super big heel is nothing but a thin plastic shell. We'll see.

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, 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).