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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 was talking to some people at the boatyard this morning and heard that in a conversation the other day I was described as the guy in the green boat who always wears tall boots. I’m getting known …

As a person who wears short shorts with knee high boots and a Hawaiian shirts occasionally in the summer, I see nothing wrong with the look, EXCEPT the height of the boots. But at 70, I could be delusional (but I doubt it).

Using the word "delusional" is a translation from my wife's English to the King's English, but I think it's a pretty accurate one. The only thing that has changed in the last decade is the scope and intensity of her disdain. Before, she believed that every single person was staring at me every minute we were in public, and probably pointing and laughing. Now, she believes that every person who gives me a compliment is merely teasing me. There is, of course, a kernel of truth to both of these. I'm sure that a small percentage of the time, both are true. Let's face it, I'm not for everyone.

While out shopping the other day, I saw a woman wearing shorts with knee high boots. The boots are what I would call flat, but they did have modest separate heels maybe 1 1/2" tall. Her top was long sleeved and sort of flowy. The shorts were short, but not shockingly so. I approved of her outfit in theory, but something seemed a little off. It was when I met her in another aisle that I realized that the woman had to be at least 60, and possibly more. She was with another younger woman who appeared to be her daughter. The daughter was dressed normally for an American in sweatpants and a t-shirt at least one size too big. Because of hair dye and good physical appearance, I had at first assumed the woman was much younger, and yet there was this indescribable quality that made me think, "Why does this outfit look less than awesome on her?" Don't get me wrong, I'm not being ageist, I don't believe there is an age when women should dress a certain way, or stop dressing a certain way, but this was not really happening for her, even though I cannot point to any one thing. I wouldn't have thought another minute about this encounter, which did not involve any conversation or contact, but here I am, days later, thinking about it for one rather selfish reason: Do I look like that when I'm out and about? I know I shock people for a completely different reason, but I think I do the shorts thing rather better. Perhaps I am delusional, as my wife has insisted I am for some time.

Tough to remember, because i progressed gradually. All started with 2" block heeled Frye Campus boots and cowboy boots, always looking for cowboy boots with taller heels. I made many thrift store purchases also. My first actual purchase was online, a few pairs of Pleaser boots.

My first heels were acquisition from my first wife in about 1977-78. It had (I think) 2 inch heels. Had them till the mid 1990's when they wore out. In 2011, I determine that my numerous ankle injuries was due to men's shoes not fitting my foot shape, so I switched to only women's shoe. No ankle issues since. I Started with mild 1.5 to 2 inch heels. It took a lot of nerve wracking to get over the clicking sound, but now I enjoy it. In February 2015 I had a (medical) need to raise a heel 4 inch, but I couldn't raise just one foot, so I went to DSW and found a pair of 4 inch heels in the clearance area. Put them on and within a minute found my balance and have been high heels since.

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 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.

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.

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!

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