My summer shoe uniform is Reef flip flops or Sperry boat shoes- comfy and casual but still slightly nicer looking than sneakers. I am looking for something else that will transition to fall and early winter (in New England, so come winter I'll be in winter boots 98% of the time). Must be comfortable enough to walk a few miles a day.

Any suggestions? I don't mind spending a little more since I'll wear them every day, if they are really comfortable (like, under $150 would be OK for something perfect). Thanks!