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Make sure they fit properly too. The foot slides forward a lot in a stiletto which often makes it loose around the heel. You can't afford this to happen - make sure there is a snug, non-slippy fit round the heel.
back in the 80s I would wear them all day every day. I didn't drive so that included walking a mile to the station and then half a mile to the office. I could run for a bus or train without any problem and would often stay out all evening dancing or standing up at gigs. Nowadays I live in Uggs and Skechers and all my lovely heels have been given away. I have a couple of pairs of highish wedges but they are only worn when I can be sure of getting a cab to and from my destination!
I was also a tiny size 8 with a flat belly, no broken veins, thick lustrous flowing hair and the complexion of an angel. And did I appreciate all that? No, I was shy and insecure and stuttered if anyone spoke to me.
I live in them from Mondays to Fridays (plus the occasional Saturday). I've been doing ballet since I was a kid so stilettos aren't a problem for me. What's important though, is finding the right one. Proper fit, proper height, proper support. Get any of those wrong and they're a nightmare to walk in.