I've started jogging this year, and on the advice of some friends, got some nice running-specific shoes, that were about $140. Saucony Cortana 3 or something like that. I had been running in some old beat-up Nike Shox that must be close to 10 years old.
Weird thing happened, though. I'm not in the best shape, so it took me a bit to build up some endurance. Started off, with the old Shox, doing about 5.5 miles, but with more of that being walking than I'd want to admit. I ran about a mile, but then had to stop and rest, and the remainder was a combo of walking and running. Well, the last time I ran in those Shox, I jogged 3.9 miles without stopping at all, and a combo of walk/jog the 3.9 miles back. So, I figured I'd go even further in these nice new running shoes. Nope...right calf started hurting after about 9/10 of a mile. And today, six days later, I STILL feel some pain in it! Wonder if the shoes just need to be broken in, or they're working my leg in a different way from the old beat-up shoes, or what?
I remember the first somewhat-expensive shoes I ever got as a teen. $40 Converse "Star-Tech" leather hi-tops, back in 1984. Adjust for inflation, and that's about $90 today.
As for dress shoes, I haven't had to dress up for work in ages, but I probably paid about $70 or so for a pair back in the early 90's. They're long since gone now. For a situation where I have to dress up, I have a few pairs of boots I can pass off with a suit, without looking like too much of a redneck!