For anke-support issues (read: messed up tendons from years of playing second row in rugby), I wear boots almost exclusively. I've been putting at least 5-7 miles on my thursday boot captains almost daily for the past 4 months and have yet to see an issue, soles are fine, leather's soft and supple but still supportive. For a little more you can get a better boot probably but don't let the bad reviews scare you off if you like the look or that's your price point. Mine are doing just fine.

That said, for real punishing weather or hiking I've got my redwing Iron Rangers so if you're looking for a "swiss army" boot, you might want to look elsewhere.