At first it might feel weird because it looks like a thick platform sole, but you get used to it. It sort of sometimes feels at first as though you are going to "walk out of" the shoe, but it stays on.  Would have preferred the high top version, but they were unavailable at the right price (prohibitive!) Classic design from last century still works. Very comfortable and you can wear them all day without thinking about your feet, because they aren't hurting! Fits true to size.

As mentioned, takes some getting used to. Wouldn't call it "breaking them in" but more like "training" them to your foot, as you would a good hat. The more you wear them, the more they mold to your foot for a custom fit and feel.