@f When I was younger I wore heels regularly. I found them comfortable. But I did not wear extremely high heels, just regular high heels. I was in pretty good shape then and had good balance, and I didn't have to think about how to walk in them. It would not be the same now.
I dated a tall man for several years back then. I am not tall. Wearing heels when we'd go to a dance or when we went to some other kind of dressy event felt very natural; I liked being closer to his height.
That said, it was definitely partly due to my environment. It was expected. I did not mind, but that's because I kind of did not know there was another way. I led a fairly sheltered life as a youth.
@f Well, once I moved away from the small town where I was raised, I rarely wore them. Less and less as time went on. By the time I was 25 I probably never wore them anymore.