I didn't believe the size chart. I ordered wide calf (casual boots in wide calf are usually too wide for me). The measurements listed for the wide calf didnt seem wide enough but lots of boot have stretch gussets at the top and the leather relaxes with wear. I couldn't even zip these past my ankles. I do not have wide calves, in fact, I wish they were more muscular, but apparently they are too big for these boots by a lot, and the stretch gussests arent nearly long enough to help. Even the Xwide wont fit. The leather is very very very stiff. It will require a long soak in the tub, probably multiple soaks in order to get creases that won't hurt your ankles.But otherwise, they will probably hold up fairly well to repeated use.