Every pair of Dexter shoes I've bought has been awful on my heel. I'm talking two pairs of socks and moleskin just to prevent blood and blisters. I inadvertently bought a different pair at Payless which at least looked better. Just as painful to wear, however. This particular pair looks just like what it is--a cheap, horrible pair of dress shoes that wear out too soon if worn for more than an hour at a time. Invest in something better quality, for the sake of your poor feet.