Gige

@Goose @CrushedVamp Welcome to the forum! I believe that you will find many of the active members to be encouraging and supportive as you progress in wearing heels out in public. I find it to be very comforting to know that what I have and I am currently experiencing, others in this group have also done the same. Thus, that which you share with this group will be very familiar to most everyone and the advice you receive/can find will be very helpful. On that note, allow me to offer a few suggestions. First, read through many of the threads started over the past year or so. As I started venturing out in heels about a year ago, I, too, had many stories of success as well as many questions. I found the responses, encouragement, and advice in the responses to my postings were invaluable. You may not agree with all that has been offered in the words of each individual but for the most part, I have found that which they wrote to be enriching and rewarding. For me, reading the stories of other men wearing heels in public was the motivation I needed to take that first step, both literally and figuratively. Within a year, I have gone from “Oh god! Someone may have seen me in heels!” to “Someone saw me in heels. I hope they thought my skirt and top matched my boots/heels!” I often receive compliments on my outfits and that never gets old (and/or tired). Second, be sure to share your stories, thoughts, and comments with the group. Again, many of us can relate to your feelings and will be able to offer tips, pointers, and if needed, cautions about wearing heels in public. I find that writing about my initial experiences of wearing heels in public was very helpful in processing all of it. Likewise, you will always get a response to your posts. Building confidence in wearing heels in public varies from individual to individual. Some can throw on a pair of heels for the first time and head right out in public without a care in the world. For others, it may take a bit, and there will be a few who may still be hesitant for a very long period of time. Finally, do not feel stupid, silly, ashamed, or otherwise if you truly want to wear heels out in public. There are members of this forum who range from just wearing only heels to individuals like me who are either genderfluid or fully transgender (I have started gravitating to the latter) but what binds us together is that we all wear high heels. The how, when, and where you choose to do so is entirely up to you and I hope that you will eventually become like other members (myself included) who prefer heels to other footwear. At first, yes, it is going to feel as if the eyes of the world immediately fall upon you when step out in heels. With time, practice, and determination, that will change. Again, read through some of the older threads and look at he outfits some of the members have worn out in public. When I first started wearing heels in public, I dreamed of the day I could wear a similar outfit in public. Now, I do and want “everyone” to see it! If you need advice, encouragement, or the like, always feel free to make an outreach!

Oh, I see you get to have all the "fun" weather! 🥶

This post is a spin-off of comments made on another thread that I thought might make a good topic of discussion on its own. As I did not want this to get buried somewhere very far down on the thread for which it was intended, I decided to just create a new topic. I have been giving much thought to the idea of what advice I/we could offer to any man who wants to venture out in public while wearing heels but lacks the confidence to do so. Almost all of the advice I have read here has been solid and offers a great step-by-step guide on how to do so. As far as I know, no one has giving advice to a “first-timer” along the lines of “Get the highest stilettos and shortest leather skirt you can find, go to a biker bar…” I agree that starting small and gradually working towards bigger steps as one becomes more confident is an excellent strategy. The term that has been often mentioned is “confidence,” and I agree that such is essential to a man wearing heels in public. The term “confidence,” however, may have a different meaning to everyone and thus, how such is defined may be open for some degree of debate. I would not disagree with the notion that having confidence is of critical importance, but I recognize that how long it takes for any of us to reach the point of where such exists is dependent on the individual. That which has recently dawned upon me is that there are certain facts/truths that any man who wants to (or actually does wear) heels out in public has to accept. I would argue that in order to build confidence, one must be seen in heels while in public but yet, being seen in heels while out in public is that which we fear. This fear, in turn, prevents an individual from heading out in a pair of heels, which, in turn, prevents the building of confidence needed to overcome the fear of heading out in public while wearing a pair of heels. As just over-explained here, this can be a vicious circle and breaking it may be easy for some, take bit of time for others (like me) or cannot be broken by the rest. I think the key to breaking this cycle begins with the recognition no matter where “we” go, what “we” do, or how hard “we” try to cover our heels, someone will always notice what we are wearing on our feet. Accepting this reality/fact is, as I see it, truly the first step to heading out in public in a pair of heels. If one accepts the fact that they WILL been seen in heels by someone somewhere, and such is the key to building confidence, then “the rest” will eventually come. In time, being seen in heels in public will not be an issue to the wear of such to the point where one may wear heels that other forms of footwear. There have been instances where I have been out in public while wearing heels that have been 90% covered by long pants/jeans and yet, someone notices by directing a compliment to me on what I am wearing. Given what I have learned, I do not know if I would have handled those “early days” differently. Speaking from my own experience, however, now, there is nothing more exhilarating and a confidence builder than being seen in a pair of heels, regardless of if the heels are fully exposed or not. It speaks so much of confidence to go out in public to do one’s whatever, and not give a single care to who sees me or what they think about what I am wearing.

OMG!!!!! I am sooo insanely envious! I have my eye about three pairs of boots from FB but, unfortunately, there are some other pressing priorities at the moment. Could I ever so kindly ask you to share the details of your experience in ordering these wonderful boots? Were there any issues with the fit? How long did take to receive them? I absolutely want to get a pair from FB but also want to ensure they will fit me "just right."

That is awesome! I cannot say that I ever have been in this position but if such were to happen, I would be both flattered and delighted.

When I initially read this post, I thought about what I could say or offer in order to help an individual regain confidence/self-esteem that had been lost due to the comments of others. Shortly after I “came out,” I had a similar issue with two women at my office and wrote about them in a previous post which was very helpful in dealing with them. As I was making the long, flat, boring journey from my residence to the Chicago area for Thanksgiving dinner and back home today, my thoughts were focused on this situation because the drive was long, flat, and boring. Before I commence with my answer, I wish to make it known that what I am expressing here is my own opinion and I do not mean to insult, disparage, or speak ill of anyone. In all truthfulness, however, this situation, as it is presented, offers some troubling “red flags” of greater concern and there are many areas that I believe should be addressed. Just to offer my credentials to support my position, I have been married for 32 years and hold a graduate degree in behavioral sciences. First, “…when we first met I told her early on about my high heel infatuation and it's kind of a deal breaker if it's something they wouldn't be into exploring or doing....” This is troublesome because it signifies that the relationship is conditional and based on an unsuitable foundation, that being the wearing of heels, rather than on more metaphysical attributes such as love, admiration, compatibility, and shared interest/outlook on important concerns (e.g. child rearing, religion, etc.). Turning away a potential mate/partner because she would not be willing to explore or actually wear heels is quite unreasonable. This puts the desire to see others wearing heels in front of qualities that are far more important that help determine suitability of a potential mate. This begs the question of if you can truly love someone who does not/cannot/will not wear high heels. The mere fact that this issue was presented for discussion makes me believe that your wife no longer wearing heels is highly problematic for you. Second, “Years have gone by and I've got her over probably 200 plus different heels over the years.” This is extraordinarily troubling. The question I must ask is who made the decision to purchase so many pairs? If it your wife, then I would argue that she is taking advantage of you because the math shows that regardless of when the first pair of heels was purchased, this averages out to more than one new pair every month. If it is you who sees a pair of heels and purchases then for her, then you are feeding your own addiction. Even if it could be considered 50/50 split, this is still troubling - what other items of which you own do you have 200 examples? The only item of which I own 200 or more examples are songs on my iPod. Although I cannot conclusively make the determination as to who buys a majority of the heels, judging by the way the sentence is phrased, I am led to believe that it is the author who does so. I would be inclined to think that, at first, receiving/getting a pair of heels would be a nice gesture but after a while and due to the frequency of such, it would grow old and the thrill of it is lost. Thus, when new pairs of heels continue to be given/received, it sends a message of expectation. Also, think about it in this light - if one pair of heels were worn once a week, it would take about four years to wear every pair just once. That is horribly wasteful. Third, “I'd love to find another couple who lived closer to us [whose] wife is someone who would/does/wants to wear heels when going out so my wife would hopefully regain the confidence she's lost by negative people…” Simple question - for whose benefit should she wear heels, yours or hers? Referring back to the first and second points to some degree, it seems that your hope of having your wife wear heels again may be rooted in satisfying your own desires for her to do so. As you mentioned that you have an “infatuation” with heels, that you have “got her” over 200 pairs, and you want to see her start wearing heels are indicative comments that your primary concern is focused on satisfying your own desires. Wearing heels does not always “make” an outfit as I have recently learned that an elegant pair of loafers can be just as classy and chic as heels if they complete a well put together outfit of matching and “proper” fitting clothes. Finally, “[T]he only thing you should be concerned with is what I am/would think about an outfit/ a pair of heels/ where you're wearing them…” Sorry, but this really struck a nerve. When my wife and I head out, that which is most important to me is that she wears attire in which she is comfortable and is appropriate for the occasion. There have been many occasions where my wife has asked me if I believe, based on the outfit she is contemplating to wear for the evening/event, if it would be over/under dressing or the items match (Color, style, etc.). Then, and only then, should she be concerned with my opinion. Otherwise, what I think of what she is wearing is immaterial unless I feel that which she has selected is grossly inappropriate for the occasion (e.g. flip-flops at a black-tie event, or a cocktail dress to a Kindergarten graduation, etc). If my wife should wear an outfit that is worthy of a compliment, then I will make certain that I express such to her. At no point is there so much as minute expectation on my part that she should be the least bit concerned about what I think of her outfit. She is the person wearing it and her physical comfort in doing so is all that matters to me. My wife has a few pairs of shoes that I think are hideously ugly but she loves. If she wants to wear them out and about to an event when it would be appropriate, then unless there is some safety issue in doing so, my opinion is irrelevant. I do not know what was said to your wife by others but I think there is more to this than just their comments. Truth be told, those making such comments may have a valid point. There is a time and place to wear heels, and a time and place not to wear heels. Although I enjoy wearing some form of heels when and where I can, there are times when grabbing my purple, or blue, or red Vans, or flat heeled riding boots is far more practical, comfortable, and wiser than going for a pair of heels. Based on what is written in the initial post, especially in regards to that which is/would be a “sort of a dealbreaker,” I get the impression that there is some sort of expectation about when and where your wife should wear heels on your part. As I see it, based on how many pairs she has, it seems that wearing heels 24/7/365 is what is desired. If so, this is unhealthy for any relationship. I hope, however, I am wrong.

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.

Yes, indeed! Quite comfortable....I haven't worn them for a bit and kind of forgot how much I enjoy walking in such tall heels. I have been wearing more lower heels for work.

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!

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!

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.

I think my fear of breaking off a heel, especially for a stiletto, has been the greatest concern that "prevents" me from wearing them. I understand that it is the quality, and thus, strength of the shank and not necessarily how well the actual heel is attached to the shoe that may result in breakage. One of the "issues" I have noticed about stilettos is that of what I call "heel flex." I have and had stiletto heels in which, when the bottom of heel makes contact with the ground, it firmly sticks in place but as the foot bed comes in contact with the ground, there is a slight bend of the sole, pushing the top of the heel slightly backwards while the bottom does not move. When the foot is rolled on to the ball of the foot, the heel "flexes" backwards. My concern that the repeated flexing/bending, ever so slight, will eventually lead to a fatigue failure and the heel becoming detached from the sole. This flexing/bending, however, is not limited to stilettos as I have noticed it happening to other heels, even block heels. I am not sure if this is "normal" or is a reflection of the quality of construction of the shoe/boot. I have learned that heel breakage is not limited to stilettos or other taller height heels. Some time ago, I was shopping at a larger retail store while wearing a pair of "flat - heeled" riding boots. Shortly after I entered the store, I noticed that the 1" heel on the right boot was making a strange sound. As I looked at the right heel, I noticed that it was barely attached to the sole as the glue holding it in place was minimally applied. I removed it, placed it in my pocket, and hobbled around the store quite embarrassed by the situation. When I returned to my car, the boots came off and I tossed them into the back seat. When I actually returned to my residence, I noticed that the left heel was starting to come loose from its sole and what followed was a sting of profanity that, last I checked, is still hanging above Springfield, Illinois, and has been known to cause some degree of turbulence for air traffic in the area. What made this situation infuriating is that the boots were a designer brand from which this type of nonsense should not be expected. I glued both heels back to the sole and sank three small screws into each heel to help secure them in place; I had no issues with the heels when I last wore them. The point to this is, what has been echoed in previous replies, materials used and craftsmanship of the product may be the ultimate factor when/if a heel should become detached from its sole, is right on point.

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."