I normally only wear leather soled dress shoes, my favorite brand is Allen Edmonds and I know they make some more comfortable casual shoes as well. Try Ecco as well. Both in the $200 range but the shoes hold up much better than Rockport/Dockers/Clarks shoes.
Most comfortable shoes are by Mephisto, sure they will run you $200+ but there comfort is unmatched by any other shoe company.
Nike, which owns Cole Haan, puts its AIR technology into a lot of the rubber soled shoes in the line-up, still pricey but in the $150 range and they look comfy, just a bit too casual for my taste.
