@firefly,
I stopped with 4" heels, high back then, when I was around 25. Later an orthopedist told me I had very high arches and (thus) metatarsals that that didn't "roll" like most peoples; instead they sort of slapped the concrete sidewalks. I was ok with more moderate heels. The real change came when I found out I love Danskos, which have always seemed to be made especially for me. I could walk miles in cities with those (or my pair of nike air max).
Not the prettiest shoes I've ever seen, but good for my feetsies.