Air Jordan in wingtips? It used to be that dress shoes were clunky and painful to wear, but that’s all in the past. Cole Haan, which has been nurturing fine gents’ feet for 80 years, has the perfect answer to stale, pained toes and ankles in the office: Nike Air technology. Sounds crazy, huh? But just take a look at these Air Madero Cap Toes, with a soft calkskin outer and the cushiness you’d expect from Nike tucked away in your heel. You won’t sacrifice style, either. Cole Haan handcrafts these babies to achieve the silky smooth look in every pair. But if the office Olympics come around, we’ll put our money whoever is rockin’ the Air Maderos.

Buy: $198.

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