I have purchased Bostonian cap toe oxford type dress shoes for over 20 years and have always been very satisfied with fit with the ability to wear them 12+ hours a day. My shoes usually take 2-3 days to break in and then they fit like a slipper. I am disappointed with this Andover model. The shoe never broke-in even after 4 months of wear (I was on assignment and was not able to return/adjust/ replace). The sizing from the last was terrible, the shoe bent at all the wrong spots and was uncomfortable, period.