One of my favourite shoes of the past 5 years was the Cole Haan Lunargrand wingtip. I loved the lightweight Nike outsole that gave some sneaker character to classic shoe styling.
The newest iteration of their "sneaker meets classic styling" is the Zerogrand. I got my hands on two different pairs: the more classic looking Zerogrand Oxford and the Zerogrand Waterproof Tall boot. In the past number of years athletic shoes have become more and more flexible to allow the natural movement of your feet. The deep grooves in the outsole adds this type of flexibility to your dress shoes. I haven't tried it yet, but I bet you could comfortably jog in these bad boys.
