Tossing the heavy shoes in favor of something lighter? Try these wool ones with a comfortable ribber sole: the upper is charcoal gray to hide scuffs and smears (and match with more than just your top jeans), and oxblood leather finishes off the look quite smartly. This fresh new approach to the sneaker comes in sizes 8, 9, and 11, and has interestingly vintage appeal. Don’t design always go full circle? [$90 at tobi]