These are very comfortable shoes in every way EXCEPT the heel. For some reason they are shaped in a way that they cut in at the top of your heel, around the ankle in back. It's confusing because I can tell they would be perfect if they were straight in back instead of C shaped. Not sure if it's something I can fix by breaking them in or not... to keep them or not to keep them?? I've already tried an insole, but it didn't make a difference and really, if I need insoles for a pair of sneakers then something is wrong. Otherwise, they're damn cute! I love the soft leather and classic, retro style. They have squishy crepe soles, like other Clarks Originals. If you are familiar with those then you know how good that feels. I have them in white and they make my size 8.5 feet look small. I've already tried them on with skinny jeans and leggings and they look great. They're more grown-up than Converse and avoid looking cheap and trendy, like sneakers you find in a store that caters to teenagers and rhymes with Smurban Droughtfritters. Ok, I may have just convinced myself to work with them. Maybe some rubbing alcohol and a little stretching around the ankle with make them not cut in. Cross your fingers.