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I remember the 90s as being some pretty dark days as far as being able to purchase decent looking shoes. My memory isn't what it used to be, but all I can remember is giant ugly platforms with lugged soles, and the jeans that girls would wear too long on purpose so that the hem would get stepped on and get all ratty looking. I also fail to remember my very first high heel purchase. I can remember my first pair of heels, but I didn't buy them, I actually found them. Inside the bass drum of the drum kit in the high school choir room. I know they were some girl's show choir shoes from a previous year, because I recognized them. I paid attention to such things. They sat in that bass drum for quite some time, probably unbeknownst to anybody but me, and I finally decided that they needed a better home. In retrospect, they were kind of ugly. I'm not going to waste a lot of time trying to recreate their likeness, but they were very 80s looking open-toed pumps with fake stacked heels, dangerously close in lack of height to being kitten heels. And they actually fit me. I remember wishing many times that they were 4 inchers, but alas, they were barely half that. I have to fast forward us about 25 years before I bought actual real heels for myself to actually wear in actual life.

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?

Yes, even if the caption is inaccurate. Shouldn't that read "World of High Shafts?"

Fashion is all about contrived obsolescence. Styles are here and gone in weeks and either you buy them or you don’t. It’s a shame but it’ll never change

I would have to agree

Indeed walking a towpath in tall boots and jeans, jumpers and high heeled boots in the supermarket will never grab the headlines, but people here have grown used to seeing me in my tall boots - to the extent that one day when I was wearing hiking boots, one of the locals said he didn’t recognise me at first when he saw me from behind

Precisely. Regular guys wearing nice boots and outfits that isn't some crazy over the top design for the runway. But, I guess our "carpet" is our day to day travels going about our lives in public.

Now these look great and fit nicely

So true, I always know the brand name of my boots, sometime the model name as well. But, good luck finding them...

The wife and I made a Costco run yesterday. Sometimes I take this approximately monthly opportunity to be a little ambitious with my outfit, and sometimes I don't. Yesterday was the latter situation--I didn't have the energy or desire to wear truly "high" shoes. I literally need to warm up for half an hour to wear "high" shoes anymore. So I chose my Söfft ivory sandals (model name unknown), which are effective 3 1/2" heels. While in the store, I was accosted (and yes, that is pretty close to the right word) by a young-ish woman, who demanded to know where I got my shoes. I told the truth, and said I didn't remember exactly. I kind of hate doing that, but these days, not only is it the truth, but I have to inform people that this particular model (pretty much the case with whatever I wear) hasn't been made for at least 15 years, and good luck finding it. Thus far I have refrained from pontificating further on the state of current fashionable footwear, which I find either boring or ugly, or both!

Yes those are very nice - a bit high for my tastes, I like just over the knee, but the heels and overall styling are very nice indeed

Another pair that would look good on men. Believed to be by Biondini, but not sure if still available.

I suspect you’re right. They need guys like us on the carpet, who actually wear boots and heels!

For sure. Furthermore, these boots and outfit were probably just grabbed "off the shelf" and given to the model to wear, no time for custom fitting, etc.

To be fair, there is so little style guidance out there for men in heels or tall boots. You can find no end of fashion stories and articles for women looking for inspiration on what to wear with boots and heels, how to pair things up, but for men there is nothing and the few examples one sees, on Instagram or in the catwalk, are generally bizarre, androgynous, or overtly gay and thus offer little guidance for an average Joe who fancies adding a touch of theatre to his look without going over the top.

Generally, I agree with the comments that have been added to this thread. The boots DO look like waders and as much as I appreciate the actor wearing thigh high boots in public, this outfit is somewhat of a mess. I also think the jacket is too long and should be cut off at the waist. I, too, read the article on CNN and also appreciate the lack of judgement about the style choice.

On one of my early trips to Antarctica back in the 90s I spend several weeks on an icebreaker and during that time obviously came to know everyone - about 90 or so people (crew, scientists, tradesmen working at the bases) After spending time on the base, and changing over the staff, we headed back home again. One night at sea I found myself talking to what I thought was one of the new guys - returning home after a winter in the ice. I introduced myself and asked his name. He gave me a funny look. It was one of the marine biologists, a guy I’d played scrabble with many a time in the preceding weeks at sea - only he’d had a great bushy beard then. He’d shaved it off while we were at the base and I completely failed to recognise him.

Yes, as someone who wears tall boots a lot I always wear skinny jeans so they can fit nicely in the boot shaft instead of ruching up and/or having the fabric billow out over the top of the boot. His boots are so high though - much too high for my tastes - and so loose (again, much too loose fitting for me) he could probably get away with wearing even zoot suit trousers under them.

I wonder what he's got on underneath those boots? I personally find that I cannot wear traditionally tailored suitpants with tall boots, because there is too much fabric there to stuff in, and it ends up billowing out in unflattering places after a bit of movement.

The "once-over" was not what I would consider a negative one, it was a curious one. Realize that my assessment is based upon a split second impression that was made before I realized who the guy was. lHad I not been in a hurry, I would have said hello, and the conversation would have been pleasant, if not brilliant. He is also in construction, though he is now retired. How we have not run into each other in the last 10 years, I have no idea. I see his sons around town often, and I still to this day do not call them immediately by name, because they are identical twins. From a distance, they still look very much alike, even though they are now approaching 50. And I can attest to context being everything. It is very jarring, and sometimes downright confusing to meet one of my colleagues outside of work. For one thing, people can look very different without a hard hat!

I saw that article too - or an article anyway. Perhaps there were others. I liked the tolerant tone of the one I read (on the CNN website) It was far from disparaging the notion of tall boots for men. I’m not a fan of the style - too much like waders - but to each their own. It was not outlandish. A positive response to them, as in the article I read, could well help to normalise the idea of tall boots on men. And that would be a great thing!

They are nice boots, but sure don't fit his legs very well. The important thing is that he is wearing them, perhaps helping to normalize guys wearing great boots

Not sure if anyone saw this but there was a rather public event regarding a male wearing OTK boots (but without a high heel). Swedish actor Alexander Skarsgård was recently photographed wearing a pair of Saint Laurent thigh high boots (designed for men) on the red carpet at Cannes in the recent past. There was an interesting article that accompanied this "story" about how this may be the next logical step in men's footwear trends. I did some research on the boots but information was limited. Given the designer name, I am sure they cost as much as a small automobile. Just to clarify, the picture is not mine but posted for purposes only related to this discussion.

Context is everything. It had been years and he wouldn’t have been expecting to meet you - and when he did encounter you, his eyes were drawn to your sandals. That’s what his impression would have been based on, and the corridors down which his thinking went. Small wonder he didn’t recognise you. Had you been in jeans and work boots I think he might well have recognised you

OK, so the guy that "gave you the once over" was the same guy at the counter, correct? When you say "once over", did you feel it was a positive once over? Any curiosity as to how the conversation would have gone had it occurred? I have reacted the same way when encountering fellow crewmembers on a layover.