Gige

Glad to hear it! I, like you, recently traveled and also did not pack a single item of men's clothing. The reason I did not do so was not necessarily by choice but due to the fact that I recently purged my wardrobe of all clothing that was too large for me! So, I have somewhere around 1/2 items of men's clothing. I would have jettisoned all of it but I decided to hold a few items "just in case." Interesting prediction, indeed! I suppose that depends on what one defines as a stiletto. Would you consider the heels of the ankle boots in the added photo as stilettos? If so, then yes, it is only a matter of time as I plan on where these to work in due time. If no, they are not stilettos, then only time will tell if you are correct.

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.

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!

Not to get "too" far off topic... I also have come to loathe traveling. I usually enjoy the place to which I am traveling but getting here is often such a headache! I am sure we all have horrible stories of severally delayed/cancelled flights, lost luggage, lack of service, etc., and my list of that which bothers me about it is quite extensive. Not to disparage anyone who works for the travel industry in any capacity, but it seems that any way every last nickel can be squeezed out of the traveler is going to be done. This fee for that, that fee for this, a fee for charging a fee... I did, however, enjoy traveling in heels and, in particular, strolling around the terminal in a skirt and boots for all to see. As much as I wither at the prospect of the next flight I have to catch, I can not wait to do it again! Nope - AA from BOS -> STL.

I was last in Boston 38 years ago, so to me, I cannot count those as 'having been there" by any stretch of the imagination. THanks for the compliments.

I have a pair 12cm heels and walking in them can be a bit challenging. I find that getting the muscles around the ankle loosened up a bit beforehand is very important. I will not lie but walking out and about in 12cm heels was a thrill!

Surprisingly, no issues with zippers setting off metal detectors.

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

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

Yep, about 90 minutes from STL compared to 3.5hrs to ORD.

First, as always, thanks for the compliments! It is great to know that others appreciate the effort I make to always present myself as being well-put-together. I tend to believe that there is only so much one can say on any given topic no matter how well versed s/he may be about it. Likewise, we tend to get tired of focusing on the same topic time and time again. A few years ago I completed my studies for my Masters degree and was strongly encouraged to pursue a doctorate. Spending up to four years of my life on a single focus, however, was just about as appealing as eating dirt. I feel the same about any subject - there is a time when I need to take a break from it if I can say or learn no more about it. This even applies to heels - there is only so much one can say about it. Yes, I am very attuned to both taste and style so that I always present myself in a professional manner. Whereas yesterday's outfit was a skirt and boots, that which I wore today consisted of black kitten heel pumps, black pants, a black and white striped sweater, and a black cardigan. Not at all to disparage her, I felt as if I took my outfit cues from a casual day for Vice President Harris. I think attire standards have sunk so low in recent years that there is no longer a line between casual/comfort and anything else. I recently conducted an interview of an individual who was the target of an investigation and asked a newly hired colleague to join me for such. I told her that the boss wants us in professional attire for such activities but leaves it up each individual to determine what form that takes. My colleague arrived wearing an oversized shirt dress and Birkenstock sandals. I had to stop and shake my head in disbelief that anyone could think that such an outfit could remotely passes for more than 'lounging around the house' attire. Despite being "out" at the time of this interview, I still wore a dress shirt and a tie. I am all for higher heels and hemlines but, again, within reason. You will never see me wearing skirts/short that are so miniscule they could serve as an ice skater's skirt or swim trunks. Likewise, you will never see me wear heels so high that I need the assistance of others just to maintain my balance in them (i.e. Lady Gaga). Thank you so kindly for the compliment(s) - always greatly appreciated. I tend to think that confidence is like a snowball on a hill - once it gets started, it will be become bigger and bigger until it comes to a stop. Once a little confidence is built and the person is will to keep building it, it will continue to grow stronger and stronger. As this point I have such a "who cares" disposition that it may be frightening to some. I am not at all "in your face" about it but more of a notice if you will and think what you want - I really do not care about either. I have always wondered about how many men I see who are secretly envious of us. ORD holds a very special place with me - I have traveled in and out of that airfield so many times. In fact, all of my recent international flights have been from and back to ORD even though I live much closer to STL. If I left STL for an international destination, chances are that I would have to transfer at ORD. If you are ever in Chicago for a while, make an outreach and I will see what I can do. I can not promise I can get there as I have very limited free time from work. I am, however, willing to give it a try if possible.

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."

October Entry! Let's go boys! 2024 is nearing and end! 😁 Second October Entry! Outfit recently worn to the dentist!

Thank you ever so kindly! Thank you ever so kindly! I may not have the elegance of such wordsmiths as Ray Bradbury or the like, but I do enjoy writing essays when I get the chance. First off - a huge thank you to all who responded! Your comments, thoughts, and critiques are always greatly appreciated. It always seems to be the case that I wake long before my morning alarm and begin mulling the most important question of the day, "What the heck am I wearing to the office?" Most times that which I wear is largely dependent on how my feet feel - somedays certain shoes are just not going to work for me. So, when I find a pair that do, I will put together an outfit around those that will work. After I rolled my old bones out of my cozy bed this morning, I quickly checked to see if there were any responses to this thread. Upon reading those that had been posted and the encouragement within them, I decided that today was going to be the day I took my style of dress to a new level. I recently purchased a pair of beige-ish just-over-the-knee boots and decided the time to wear them out and about had come. I matched them with a khaki knee length skirt, brown sweater, halloween themed accessories, and off I went. Admittedly, I was a bit unsure of the outfit as the boots, in particular, were outside of my comfort zone in terms of what I usually wear to the office. After reading the first responses to this thread, however, I recognized that if those who commented on this topic can wear stilettos, OTK boots, etc. to work, so can I. As I got to the main entrance of my building, I held the door for a woman who has a bad knee and has trouble walking up the three stairs from the parking lot to the level of that entrance. "Good morning!" I said to her as I see her often and always hold the door for her, to which she replied, "Good Morning beautiful! Love those boots!" What a way to start the day! I told her that this was the first wearing of them so they were a bit tight around the toe box, which they were, but loosened up a bit by the end of the day. Over the course of the work day, many colleagues observed what I was wearing, even my "big boss." It was honestly a thrill to be seen in this outfit and a tremendous confidence builder. I was dancing on "Cloud 10" at the end of the day as my outfit had passed muster for being acceptable. Then again, compared to what others wear in my office on my days, I could waltz in in a bathrobe and still look more put together than many of them. I will admit that I felt incredibly alluring. I left the office today knowing that OTK boots and slightly above the knee skirts can be worn while still retaining a high degree of professionalism. It is my intent to push the boundaries just a bit to incorporate a bit of pizzazz into my outfits when I can. The heels and hemlines will be slightly higher, and clothes and accessories will have a bit more "spice" to them. All within reason of course. So, to those who have already been down this road, my sincerest thanks for setting out a trail for me and others to follow. It is my intent that when I am next in St. Louis, to go back to my bank and personally thank that banker for inspiring me to follow suit. Eye catching/head turning outfits can be professional. Thus, the answer is yes, I was wrong!

Yep - have that problem of being overly wordy and long winded. If I could only get paid by the word, I would never have to work again (Think Herman Melville).