Cole Haan Air Ashby Oxford

Plain, simple, and yet surprisingly dignified, the Cole Haan Air Ashby Oxford ($160) is a solid all-day dress shoe option, transitioning well from khakis or chinos to nicely tailored denim. It features a genuine crepe sole for natural cushioning, a plain-toe design, a hand-burnished leather upper, leather and fabric lining, and concealed Nike Air cushioning for maximum comfort.