These took only a day or so to break in and were pretty comfy from the beginning. I only had them a couple of days, but wore them on a 5 day vacay in DC. We did a lot of walking (~40 miles) and while my feet were tired at the end of each day, they never got sore. These looked much better than wearing sneakers around the city and they still look good for work. My only complaint is that on one of the toes there is a 1"x2" spot that is noticeably lighter in color (grey instead of black). I would have exchanged them, but I did not have time before going out of town.