I've been wearing these for the past couple of weeks to go to the dog park when it's cold (and muddy) and so far so good! I can fit my orthopedic insoles in them comfortably and I think there's enough room to wear a thicker pair of socks. I just haven't tried that yet. I do find they're a bit stiff, but they probably just need to be broken in more. I haven't gone on any long walks with them yet because it hasn't been cold enough yet.