I wore them for a few hours yesterday and they were amazingly comfortable. I'm not quite sure about the longevity of the sole but Crown does offer a resoling service for them. Considering the softness of the rubber on these crepe soles I probably wouldn't wear these for work, probably just casual use/walking. I might considering having them resoled with leather when the time comes. My oldest pair of Redwing Beckmans are 13 years old and I've never had to resole them but they have a sturdier Vibram sole. I expect to get at least 5 years out of these. If you're wearing out soles fast I'd recommend the Vibram with heel plates.