Wore my new boots I got for Christmas today, and they're surprisingly painful to walk in over concrete. But they look good. Priorities and all. However, I think long hikes through the urban jungle are off the list for these:
It's possible, but probably not. They fit great—they're not too tight or too big or anything—the problem is that the soles are a little thin, so when I'm tromping around outside, I can feel every irregularity in the sidewalk, and there's no cushion. The cold doesn't help either. They're fine inside on carpet and even flooring.