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

Here are my new boots, Light brown suede leather

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

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!

I do not know the exact date of when it occurred but it has been about a year since I first ventured out publicly in a pair of heels. As I reflect on that first instance and all that has happened since then, I needlessly can offer the following observations/realizations. First, I consider myself as “out” and the most difficult part of this journey has been just heading out in a pair of heels and telling my family and friends. For the most part, the responses have been supportive and encouraging, but my siblings have indicated that like any “shocking” news, it will take time to process. I believe that the hardest part of this experience is overcoming the fear of it and I realize that I was my worst enemy. By that, I mean I had dreamt up fears that never existed. In reality, no one has made a direct comment to me about my “en femme” attire but there have been some muttered under one’s breath comments, and strange looks and double takes. Now, however, as so many people have seen me in heels, I do not pay attention to whether or not others notice and what their reaction may be if they do. Truthfully, I do not care and in fact, I wonder if men (and women) look at me with a sense of jealousy. I’ve worked hard to trim down and have a figure worthy of showing off a bit. Second, what is most important to me is not only what I wear but how I wear it. Yes, I love a pair of towering heels with a short skirt but I do not need to wear those on a daily basis to feel good about myself. When I look at myself in the mirror before heading out somewhere, all that matters is that I love what I see, even if that is in a pair of kitten heels or in flats. To me, style, elegance, and sophistication come from knowing what to wear at the appropriate time. A pair of loafers can make an outfit as much as a five-inch heels. Third, excess is not needed. With regard to ‘Excess,’ I refer to having more heels (shoes & boots) than I would possibly wear. I, like probably all everyone (both male and female), have fallen in love with a pair of heels that I absolutely had to have only later have buyer’s remorse. I have had “too many” heels that I have only worn once because either they do not fit very well, are highly impractical, or I just do not have an appropriate place to wear them. I do, however, have several pair of heels of the same brand/model in different colors but if they fit will and are comfortable, then they are keepers. Fourth, simplicity is always best. A well-thought out and put together outfit says so much more than all else. Simple items and simple colors schemes will always be more appealing than items that carry a major designer's name. Finally, I love how I feel when I head out and I am in a pair of heels. The sound of the heel hitting the ground/pavement quickly followed by the footbed is delightful, and knowing that the sound is coming from shoes/boots that are on my feet is exhilarating. Walking past a person who can see my heels makes it intoxicating. The worst part of my day is when the heels have to come off for whatever reason. I can only speak for myself in saying that wearing heels is more than just putting “something” on my feet. Any outfit I wear, as a whole, projects confidence in the way I walk (as I walk straight up vs. slouching) and my movements. It goes beyond just how I walk, however, as I feel that I am more graceful in my movement and actions – I’ll now cross my legs and stand with my feet together vs. “man-spreading.” When I first ventured out in heels, I did so with almost all of the footwear covered as I did not want anyone to know. Now, I want to world to see what I am wearing and almost want to ask others if they see my heels. I was nervous during those first instances but now, have all the confidence in the world. It has been a journey but so one worth taking! The photo of me sitting is a recent favorite as I wore this to the dentist office a few weeks ago (teeth cleaning in style!) whereas that of me standing is that which I showed to others when I starting coming "out." Sadly, I do not have the skirt any longer as I slimmed out of it! And let me ask if anyone does/does not believe the black/gray outfit is appropriate for work.

As Shyheels suggests, boots are more durable. Maybe these would be a good compromise: On second thoughts ...