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Yes those social norms are strangling - and they serve no useful purpose. Like you, I look pretty good in boots and feel even better because I am expressing myself.

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.

I was in my teens back in the early 1970s. Modest heels for men were quite common then. I bought 2 pairs of boots (high ankle or mid calf) with approx 2" heels. I think from Dolcis, now long gone. I still have one of the pairs, black patent with a gold ring decoration. They're rather fragile now but I still wear them occasionally.