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I have been thinking about this post for a while and promise to try and keep it on point. When I started wearing heels, the height of the heel was what was important – the higher the better and I always went for 4.5” – 5.” The style of the heel did not matter whether it was a stiletto, block, wedge, or some other form. I loved such high heels because there was a certain irresistible and indescribable feeling of just being able to walk on a heel that I found to be so horribly alluring. Fast forward to November 2023 when I started wearing heels out in public. I started with 4” block heels in order to get comfortable with doing so and to date, have only worn a higher heel out to an event just once. When I started wearing heels to work earlier this year, 3” – 3.5” seemed to be a good start but for me, 4” is the limit for my own personal reasons (do not want to restart the what is/is not work appropriate debate). I have always felt that I wanted that which I was wearing to compliment the heels I chose for the day. I never felt comfortable wearing “guy” clothing with heels and as a result, began wearing feminine clothing with any pair of heels while out in public. To me, and speaking only for myself and not to offend anyone, most heels are alluring but “guy” clothes are boring and drab, thus, the two types of clothing are not compatible for my tastes. As I realized that my style of clothing to wear with my heels was starting to take shape, I began shopping for heels that matched the outfit in terms of color, style, and practicality; heel height became secondary. Thus, the height of the heel started not to matter so much anymore. Not to get off-topic, I will wear “guy” lounging clothes around my place when I have a new part of heels that need a bit of “breaking in” time before they are worn out in public. Soon, I began to feel a sense of comfort and fulfillment in the entire outfit even if I was only wearing kitten heels provided that what I was wearing with them reflected my sense of ‘haute couture.’ I, for example, love the look of tailored wide-leg pants with either a kitten heel or a shorter heeled animal print pump. Such reflects a certain sophisticated and classic elegance, a ‘je na sais quoi’ about it. The summers in my part of the world, however, can be quite unforgiving on some days which wreaks havoc on my feet; heels that fit today will not fit tomorrow if it is hot and humid. Fun and useless fact – one acre of corn stalks releases 2-3k gallons of water vapor (humidity) when they are short of maturity. When the heat takes hold, I opt for my Vans as I have several pairs in many colors which allow me to easily match those shoes to either my pants/skirt or top. Likewise, I have a very comfortable pair of loafers that are probably one of the most comfortable pairs of non-trainers I own. When I go this route of shoe choice, I still feel as great as I do when I am wearing a pair of heels out in public provided that the outfit looks great and my accessories match. Thus, I have come to realize that as much as heels are an expression of whom I am, I can still do so without having to wear 5” stilettos or the like. So, I have to ask if the height of the heel really matters?

My wife used to tell me that shoes were accessories. She chose the shoes that matched or accented the outfit she was wearing. Women’s shoes don’t have to have high heels to look feminine. In her more mature years, she would often wear very girly styles with kitten heels and look smashingly sexy. She often told me that she would leave wearing higher stilettos to me because she found them to be uncomfortable. As for me, I love wearing heels. In my. 30’s and 40’s my normal shoes had 5” heels and I enjoyed occasionally wearing higher heels. Now that I’m enjoying my 60’s, I very rarely wear heels higher than 4” anymore. My main interest has always been “Girls Shoes”, not looking like a girl. But, back on point, you’re evolutionary process is probably normal. Transitioning from pure male appearance to a male wearing female garments in public has elements of your being comfortable at the same time as your overcoming your apprehension about your appearance not being acceptable. It’s a long process. Being a female is a complex process. There is a lot more to think about, especially if you want to appear only slightly feminine. One step at a time!

Adding to my earlier reply, I think heels look quite good with men’s clothes - otherwise I wouldn’t wear them. I’ve no interest at all in anything else from the women’s side if the shop, just the heels, and then just the styles that appeal to me.

I wear what I feel for me are a combination of good looking and comfortable. I typically wear 12 to 13 cm heels, usually narrow stilettos. Like Melrose, I don't wear dresses, skirts, etc. I like "guy" clothes with heels. Your very comments suggest you believe heels are just for women and to wear them you must look like one. I'm not the only one here who doesn't agree with that viewpoint. All that said keep wearing what you feel is best for you.

In a word, yes. While I also will not (generally) wear heels with any old guy clothes, I am also not ready to delve into anything that is not bifurcated on the bottom. How this is different or more radical than wearing Daisy Dukes with heels, I am not sure, but it feels more radical. Back on point, I have got to where I am rather gradually over a number of years, and I have landed on 4 - 4.5" as the height that feels right to me. Absolute heel heel height is not as important to me as the steepness. I would never wear a 4 inch heel that had a 1 inch platform. Not only does it look kind of weird, it doesn't have the right feel to it. If for some reason the only thing available were 3 inch heels, I probably wouldn't even bother, to be honest. That's why I never really got into the Nike Sky High Dunks. Not enough lift to them.

I don’t think it does. I think at the outset the sheer novelty of wearing heels and the satisfying sense of daring in doing so makes higher and racier heels - the five-inch stiletto - seem very attractive. But as you grow more into the idea of wearing heels, and make that a part of your natural look and style, your tastes will evolve and you’ll choose heels that work well with what you’re wearing and be less fixated on how high the heels are. Your relationship with wearing heels will be more like women’s relationship with them - a stylish accessory to complete a look, whatever that look may be. when I first started wearing heels I really fancied the idea of wearing thigh boots. Now I’m not really interested in them - they just don’t work with my personal style, which is boots and jeans, knee and ankle boots mainly. Less theatre and lower heels - my favourites being 3.5” block heels. I like stilettos and am pleased that I own a couple pair, including some 12cm ones, but they are not my natural style - fun to wear on occasion, but not really “me”. I do like OTK boots but only just over the knee - and again in styles that work well with jeans and guy clothes. It’s the overall look that matters not heel height or an overemphasis on footwear

Those are nice. I especially like the boots in the middle frame. That’s just my style!

To be honest, I’d struggle to get them on without tights. Full nappa leather lining plus slim fit Some others I’ve wanted to share

I went to church yesterday in an 800 year old rural church in a fairly remote part of England - lovely old church, a congregation of twelve including the 91 year old organist, and tea and homemade fruitcake afterwards. The tiny congregation was generally older but there were some younger ones in their 40s and one of these women was in 3” heels - a bit of a surprise I was in very sturdy hiking boots. The challenge of walking two miles along the rough, stony towpath was enough in those!