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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.

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.

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

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.

I thought I'd start this thread as a bit of a finger on the pulse of what is being worn. I was thinking of this the other night when I was in a busy pub having dinner and noticing the boots and heels being worn by my fellow patrons. I was wearing low-heeled OTK boots myself - bluish-grey suede over skinny jeans. I was not the only one in OTK boots. There was a young lady in black shorts (this in winter) with some very tall black leather boors - actually more like thigh boots than OTK. I'd never seen anything quite like them. The shafts looked to be made of very nice leather and fit her well; that part was elegant. The boot part though was like a pair of exceptionally heavy Doc Martens with very thick clod-hopper soles. I don't know if contrast and aesthetic tension was the point of this, but it looked like hell. My other outing this week was to go to Leeds, an old city in the north of England. I saw a lot of people (all women) wearing heels - typically chunky heeled knee and and ankle boots with 3" heels. It was almost the norm. I was wearing black leather knee boots myself, again with low heels (my circumstances at the moment do not lend themselves to wearing heels - not because of the fear of censure but risky footing and the ruination of nice suede high-heeled boots) Again, my black leather knee bots, for over skinny jeans, passed without notice.

I think we are all more influencers than we know, and you especially. You just have this huge love of high heels that bursts through, a true passion, so I think you influence a lot more people than you give yourself credit for. That includes a lot of people on this site. And never forget, most forums have 99 people lurking for every one that posts a reply, so you might (and others on here) have far, far, far more influence than you think. But that is what being authentic does... it shows others its fine to like whatever it is that they like!

That is all so true. I also think motivation has a lot to do with it too. My wife straight up dresses for me because she loves me and knows I like it. Since she is not dressing for others attention, I think its a look she can pull off. But people also suck. My wife and I are probably some of the most humble unassuming people in the world, but we do like to dress up and most of the time are some of the best dressed people at a venue. Not over the top bling-bling, but sharply dressed. Yet we hear snide comments a lot. Most of the time it is my wife who hears them from other women in the bathroom, or walking past just loud enough to her husband but so that we can hear, and occasion for us as a couple. I think it just becomes unusual as more and more people dress down, and in doing so they either feel guilty about how they constantly dress, or flat out make the wrong conclusions on why we do dress nice. For us, its all about this: "You feel how you are dressed". Spend a week in the wilderness bush crafting it, you are going to feel gross and yucky. But dress nicely, and you feel better about yourself.

Back on the subject of feminising the male wardrobe, I have been giving thought to my taste in boots. While I like the racy elegance of stilettos, my personal style preference is for block or chunky heel knee or ankle boots. But at the same time, I dislike cowboy boots or Chelsea boots - which also have chunky, albeit not quite as high as I like. it’s not purely a matter of height but of design and lines. It’s the fitted feminine styling and elegance - as a matter of aesthetics not because I feel feminine myself.

I do have base layer thermal tights from cycling which are proving quite handy living on the canal in winter

He was like a lawyer still arguing his case after it’s already been settled in his favour and everyone in the courtroom has gone home.

The guy looks pretty good. Edgy, but not outlandish. However. . . (long pause) . . . I do admit I had to fast forward through most of the video. That's too many pictures in a single album by about a factor of 10.

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.

These days, we can easily get by with wearing colors that would have been mocked 20 years ago. I see pink shirts and even pink hard hats all over constructions sites on the regular. What has not changed, and probably will not change, is the general coverage of clothing. I'm not saying it's good or it's bad, I'm just saying that even in a modestly dressy situation, a man must be pretty much covered up except for his hands, neck, and head. The most he can get by with is a short sleeve shirt, and even that's out once you get to anything more dressy than business casual. Until and unless it becomes common and acceptable for men to wear skirts, I must keep what may be my best physical assets covered up. Even in casual situations, I still push it pretty hard with my shorts. Those are still the subject of derision every once in a while.

My latest purchase is these pumps by Shoe Republic LA. Some off-brand made-up name, I suppose. I bought them because they were advertised as having a 5 inch heel, they were 20 bucks, and I thought, "Well, let me see if I can learn to walk in them." As is so often the case, most people are not hung up on extreme accuracy with such things, and it turns out that the heels are a mere 4 3/4", making them only nominally higher than all of the Steve Madden pumps I already have of that ilk. The width of the heel is definitely on the narrow side, being slightly less than 5/16" or 8 mm. Despite my initial disappointment with the absolute height of the heel, I tried them on and walked around in them for a little while, and I think they're going to be all right. They are about the smallest, tightest shoes I'd ever want to consider actually wearing outside, but I think they will probably straighten up and fly right eventually. Once my toes uncurled inside the shoes they didn't feel too bad. The question is, where am I ever going to wear them? They are outlandish enough that I'm not really sure.