Okay, I have to offer my two cents. I really love pretty shoes, so that means I have a number of high heeled shoes (3.5 - 4 inches is the normal height for me, but the red shoes in my album have 5 inch heels and granted I only wear them for playtime. I bought them to match a red leather collar also shown in my album.) I love the way I look in heels, and I like that they make me about 6 ft tall, or more when I wear heels - I like being tall.
Anyway, I will wear heels, usually high wedges, to work when the weather is nice but I'll usually switch to sensible low-heeled or flat shoes for running errands. Currently I am 57 years old and have absolutely no problems with my feet, nor have I ever. I do take very good care of my feet though making sure to get regular pedicures and switching to flats anytime I'll be doing a lot of walking so I guess that's why. I do have heels that I will wear with party dresses, but I always take a pair of foldable ballet flats with me in my purse in case my feet start to hurt.
One other note, I always make sure to buy shoes that have a rounded toe box, I never wear pointed toe shoes, nor do I wear peep toe pumps that have a narrow opening and squish the toes together, so I guess that's another reason why I've been able to get away with wearing heels for so many years without any issues. Of course maybe I should append a 'yet' to that last statement...
Oh, yeah, since the New England winters are long and very snowy I wear flats pretty much all winter and that gives my feet a break too.