Sometimes you get it right on the first try. Case in point: the Pro-Keds Court King ($74). Originally designed as a tennis shoe in the 1960's, these durable, full-grain leather sneakers feature a rubber toe cap, aluminum eyelets, canvas lining, and a retro embroidered logo on the tongue. The padded footbeds are removable so you can change them out rather than retire the entire sneaker, and the vulcanized rubber midsole sport the famous Keds stripe, a splash of color on these otherwise understated kicks. Available in four colors, we're stuck between casual blue and traditional white (maybe both?).
Keep your feet dry and comfortable on your next hike in the classic Danner Mountain Light II Hiking Boots ($230). Featuring Gore-Tex lining for waterproof protection, a Vibram Kletterlift outsole for shock absorption and traction, and one-piece, all-leather upper, these USA-made boots are ready for anything — even if it's just a trip down to the pub. For more intense missions, check out their Tactical collection.