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My very first heel purchase,,,,,,,, and I still have them and wear them!!! Steve Madden Kyle patent leather hidden 1" platforms with 5" heel

I bought my first pair when I was in high school in the early 90's. It was a navy blue pair of pumps from Payless with a silver decorative piece on the front. The men's shoes were on the wall directly across from the larger women's sizes. I must've pretended to look at men's shoes for twenty minutes before I got the courage to go to the cashier with them.

I think I got my first heels when I was 16 and able to drive. I went to a Payless shoes, and the only memorable part of that trip was me awkwardly feeling I -had- to spew out my fake back story the clerk did not ask for. I kept those shoes and a stack of Mad magazines in a metal lock box in my closet. I think my parents were worried I was doing something illegal as when I returned from a trip to Michigan the magazines were in my closet, no box or heels. Sometime in my tween years I figured out something was up with my gender identity. I liked some girl things, and did not understand why your gender limited your life experiences. By 13 I was hitting a crisis point, and decided to just ‘be me’, and live on my own terms. Back around 1990 non-binary was not a thing. If it had I might have been far more comfortable mixing up my appearance in public.

Heyo. Decided to try a pair of Sneex. Kinda clunky to look at, but they are comfortable to walk around in.

After shattering my ankle nearly a year ago and finally finishing physical therapy, I've been making up for lost time. I've been shopping quite a bit on Mercari and Poshmark over the last couple of months. I've picked up some Lucky Brand sandals, Torrid mary janes, Nine West open toed pumps, Vince Camuto sandals, some Tom's wedges, and my favorites by far, Vince Camuto Frasper heeled sandals in black. I like them so much I got a second pair as backup. Wedges aren't normally my thing, but I still struggle to walk properly in heels. After trying them, I'm really starting have a change of heart.

Hi all: Allow me to set the situation. Today I was wearing a pair of 3”/3.5cm, dark blue, block heel pumps at the office - a pair of shoes that are very appropriate for a professional setting if one wants to wear heels (see photo). Around noon, I decided that I wanted to stretch my legs and clear my mind prior to having to switch gears from one monstrous case to another monstrous case. I figured that I would step out of the building and possibly walk to the medium sized park across the street. I stepped on to the elevator/lift and as it stopped on the floor below mine, two women stepped into the car. The conversation that followed was very close to the following: Woman #1: “It just started raining.” Woman #2: No or not heard response. Me: Oh man…that stinks! I wanted to go outside and walk around for a bit.” At that point, woman #2 looks down at my feet and says, “How can you wear those? I can’t wear heels." The manner in which the comment was delivered did not seem to be challenging me on my wearing of heels or the pair I was wearing was somehow inappropriate. Moreso, it seemed that she was expressing a general disbelief that any person can walk in heels. Regardless, the comment caught me off guard as, usually, comments given by women are very much along the lines of the fact that they love my heels and if I can wear them, then do so! Not to digress, but I often respond to compliments with a very warmly stated, "It never goes out of style to have style" which often gets a laugh or at least a smile! Me: “Oh, they’re very comfortable. The material is canvas, so there is a lot of stretch to them,” which was/is true. At that point, the doors opened and I held out my hand to signal for them to exit first and as they did so, I wished them both a good afternoon. I stepped outside and it was raining hard enough to prevent me from walking to the park. As I thought about it, I should have responded along the lines of “You should see what I consider to be high heels” or moreso, “Because I can!” Not wanting to create a scene, I responded in a nice and professional capacity. Just for clarity, woman #2 was approximately in her mid to late 40s, about 5’ 6”/167cm, and a proportional frame to her height - not heavy but not thin. She was wearing thong style sandals but not flip flops and jeans - effort level of the outfit, about a 2.5 (on a scale of 1-10). Later in the afternoon when my spreadsheets were giving me headaches, eye strain, and seizures, I decided to ask some of the other females in the office, both of whom told me they “can’t” wear heels, why such was the case. I explained to each the situation, and that I was truly curious and sought an understanding of why some women may be able to wear 5”/12-13cm heels at age 80 and others cannot wear 2”/5cm heels at age 20. I was not at all wanting to be judgmental but was only seeking knowledge. The responses I received were not only enlightening but quite helpful. It seems that foot shape and size are the primary reasons they do not wear heels. One woman explained that she has small but wide feet, as well as a low arch, which makes finding a well fitting pair very difficult while the other indicated that she had narrow feet, especially in the heel area. The latter, who is my colleague, added that if she wore a pair of pumps, her foot would not be wide enough to remain in the shoe, and she would walk right out of them regardless of height. She added that she often wears lace-up shoes or those with a strap across the top of foot so as to keep her foot in place. In a sense of friendship and humor, my colleague stated that she has often seen me wearing heels and wondered how I do it as to her, they look very uncomfortable. It is important to note that only one other person who works in my building on a regular basis (my big boss!) ever puts any effort whatsoever into presenting him/herself in a professional manner. As I have expressed on many past occasions, lounging and/or frump (or both) is often the 'style du jour' throughout the entirety of my office building. Likewise, only once in the two-and-one-half years I have worked in my building have I seen a woman wearing heels (higher than 2”/5cm) and/or a skirt for the day. Thus, the only person who wears heels on a regular basis is me, and there are time where I wear my trainers rather than heels to mix up the look a bit. So, was the question posed to me inappropriate or not? Thoughts? Can't get my photo to upload.... This is an on-line photo of the pumps I was wearing. "Midnight" by Aerosoles.

I too have wondered why I have heard that same comment over and over again, "Oh, I can't wear heels." Or, alternatively, "I can't wear heels anymore." I understand that there are some valid physical reasons why somebody can't wear heels, or at least not for very long. However, thinking back to my own experience, I think a lot of these obstacles can be overcome. It's just that overcoming the physical challenge of wearing heels requires a lot of work, and I don't think most women want to put in that kind of effort. Or perhaps it would never occur to them that it's a skill rather than just a fashion choice. In any case, it's generally a conversation that can't go well. This is why I tend to say very little in reply to such comments, and do much as you did, saying something like, "Ehhh, they're really not all that bad."

I have been wearing heels to work (and almost everywhere else) for over 10 years. I have heard the “How can you wear those? I can’t wear heels" statement hundreds of times. Here are some on the reasons I have heard and some I have reasoned myself. (1) Their feet got wider when they got pregnant and they can't get heels that fit, now. A very valid reason. (2) They ruin their feet when they were young by wear ill fitting heels. (3) They never learned how, they have weak ankles, never ran or played sports, so they never strengthen their ankle. (4) They wore running (trainers for the Brits) their whole life and never developed the balance needed to wear heels. I watched a college graduation 10 years ago and you could see those women have trouble walking in heels. (5) They buy heels solely on looks and not fit, so they look pretty but never fits right. Result: the heels hurt their feet when they walk. That leads to them to equating heels with pain.

The reason I don't see so many heels is because I spent the majority of my waking hours at a construction site. Having said that, I can remember back in the day when a building was nearly complete, the owner would give tours to groups of people (I always assumed that they were employees/bosses at the company). Invariably, there would be several women in high heels during tours through a building under construction. I can recall another job site I worked on where the female engineer would show up every week to check things out in 4 inch block heeled boots. That was the Barilla pasta plant, and the engineer was actually from Italy. That may have had something to do with not only her footwear, but her impeccable sense of style, despite being on a construction site. The concrete floors were in by that time. It's not like she was stepping over clods of dirt in heels.

Hello, it’s been a long time since I last stopped by HHPlace but I thought I’d share my first heel purchase experience with you all again. It was during a recent conversation with my sister that I thought about this forum and in particular a post I had added back in July 2010. The topic was about the first heels that you had worn and I had responded with a post about the first heels I had purchased back in the 90s (see HERE). I had attached an image of a pair of heels which were similar to those that I had purchased but it wasn’t a particularly flattering image and the heels in the image weren’t patent leather like the pair I had bought but served as a reference to the type of style. With thanks to modern technology, yesterday I took the original image and with some help from ChatGPT I was able to reproduce a near perfect image of the first heels that I ever purchased; a pair of Ravel Black Cross Strap Patent Heels. I was a teenager back in the 90s and had had discovered that despite being male and fancying females I had developed a passion for female clothing, footwear, jewellery and makeup. I had taken a liking to black patent leather too and had nearly died when my cousin offered to let me try on her patent heels one evening after high school. I had said no when put on the spot but inside I was so wanting to try them on. Anyway, I had not long left high school and one evening whilst walking home from College with my sister, we happened to be walking behind some high school girls and I was drawn to the heels that one of the girls had on. On seeing them, in that instance I just knew that I had to have my own pair of those heels and so the hunt was on to find them in the shops. It was great back then as there were lots of shoe shops in my local town centre and so it wasn’t long before I had tracked them down with a little help from my sister to the local Ravel Shoe shop. Inside the shop we quickly located them on the shelf, my sister picked one of them up and gave me a close up view. I excitedly nodded with approval, gave her the cash and she went and made the purchase on my behalf. Pretending they were for her, she asked for a size 8 only to be told that they only had them in a size 7. She looked my way to gauge my reaction knowing I was a size 8 but I didn’t care, I’d somehow get my feet into those size 7s. I remember the sales assistant bringing them out and showing them to her and me getting all giddy inside as I battled to contain my excitement at the thought of soon being the owner of the heels I had wanted so badly. I remember it being a truly magical experience! Amazing how something as small as a pair of heels can have such a hold over you! They soon became my pride and joy too and for months on end I would wear them each evening in the privacy of my bedroom. Purchasing those heels wasn’t the start of the cross dressing but they certainly helped take the dressing to another level at that time. Eventually those block heels would soon be sidelined with my first purge. What came afterwards were heels that were much more sexier than before and now they boasted much taller heel sizes too. Care to share your first heel purchase experience? Was it as magical as mine?

Good luck to you in your recovery. It looks like you've got some pretty solid stuff there--nothing too crazy, but stylish and very nice looking. I don't love wedges either, but they do have their practical purposes!

I hope you keep up your incline ankle lifts. Practice on both side. They're great for wearing heels.

Giege, I have that same pair of pumps in your picture and I love them! Happy Heeling, bluejay

It doesn’t sound to me like anyone said or thought your footwear was inappropriate, only that for reasons of their own they didn’t wear heels themselves. All of them seem to give direct physical reasons why heels didn’t work for them, not that they were somehow inappropriate for the office

Gorgeous!

It almost hurts to think about, but at the time I was just an apprentice, and the year did not start with a "2." I learned a lot on that job. Not only about how to be an industrial electrician, but how to get along with people as well. There were people from all over the world on that job.

Got a strange message on social media a couple of days ago. It was a friend from high school who asked in a private message, "Hey look--I am in no position to judge anyone, but I was wondering when you decided to wear women's shoes... Are they comfier, because my feet hurt." This really seems a little off to me for an initial contact message. No "Hey, how's it going? It's been years and years!" or anything like that. As I had accepted his contact request maybe a month ago, I can only assume that he picked up on one of the remarklably few photos of me that show my shoes, and none of those really feature the shoes. After I came home from work, I messaged him with some short answers, and he responded to them with similarly short answers. I'm quite sure he was otherwise occupied, because the conversation trailed off rather abruptly. I'm glad I did not invest a whole lot of time into an explanation. We'll see what happens in the days to come.

My first attraction to feminine footwear was for the shiny white go-go boots worn by a very pretty red haired girl in my seventh grade class. I didn’t just admire them, I longed to have a pair too. At the same time I was also acutely embarrassed by the thought that I fancied wearing girls boots. I put such thoughts out of my mind, or at least tried to, although I still really wished I could have a pair of go-go boots and thought it grievously unfair that I couldn’t. It wasn’t an obsession, this curiosity and desire to wear feminine boots - it was the feminine styling, not so much the heels themselves that appealed to me - it was more like something I’d be reminded of from time to time. Some random style would catch my eye and send my imagination wandering down those corridors again. And always with regret that such a thing was impossible. About ten years ago, I had this damascene moment when I realised it wasn’t impossible. It was only me that was making it impossible. I decided that I didn’t want to go the rest of my life having never worn heels or feminine boots, and so I ordered a pair. I splurged and bought some beautiful black suede OTK boots from Jean Gaborit with 10cm slender - nearly stiletto - heels. They were beautiful and fit like a glove, my first feels. And from the moment I stood up in them I knew it had been worth the wait. I never did get a pair of go-go boots, but I want to…

I just ordered these Freebird Detroit in Red Croc. I had hoped to get a size 11, BUT I waited too long, so hopefully a size 10 works. A 40% off Mother's Day sale was my incentive, $275 otherwise.

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.