Not so long ago, if you expected footwear to be functional, you had to opt for something besides a dress shoe. That changed when Cole Haan started making dress shoes with the comfort of sneakers and the weather resilience of boots. Their latest entry: the 4.ZERØGRAND Winter Wingtip Oxford Dress Shoe, with a traditional wingtip upper made from waterproof leather and a lightweight, cushioned ZERØGRAND sole with additional traction for the winter.