I love wearing boots with heels. I have about a dozen pairs of boots, not all with heels, but heels are definitely my favorite. You can NEVER have too many boots.
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I'm 74 years old. I've never had high heeled boots. Nor shoes, because of how my ankles don't bend as much as is needed to walk in them. This winter I needed new boots, and got offered a pair for free. A size too big, but a pair of insoles and thick socks took care of that. They aren't 5 inch heels, only about 3, but, they are actually the most comfortable boots I've had in a whole wack of years. I love my boots, and they don't hurt.