The wetter it gets, the more we appreciate rubber-soled shoes, and to be honest we don't understand why more proper footwear hasn't gone this route. Not even a high-end Italian sports car has leather tires, and the reasons for it apply equally to shoes. We think the rubber sole is underrated—as opposed to "Rubber Soul", which is about as overrated as anything can possibly get. We wouldn't mind if the rot-prone, easily-worn leather sole went the way of the leather football helmet. Shown: perfectly serviceable Lands' End Wingtips.