KEEN Denver Canvas Shoe - Men's - $61.74

Not only are the Keen Men's Denver Canvas Shoes classy as all get-out, but they also rock an insanely comfortable Keen Cush footbed with memory foam. Waterproof full-grain leather makes these kicks highly resistant to light rain, precipitation, and the occasional surprise encounter with a puddle on the city streets. Hustle through subway stations, pound the pedals on your cruiser bike, or just kick back at the local coffee house in the smooth-feeling, leather-lined Denver. - $61.74