Chaco is the well-known purveyor of some of the world’s hardiest, most versatile, and highly repairable sandals—proven mainstays of amphibious recreation. Boasting the same cushy footbed that makes those sandals a standard, their Frontier waterproof boots are equally adaptable to shoulder-season urban or forest forays where wet, cold feet might make you moody. Full-grain leather uppers and sealed seams keep your feet warm and dry in wind and rain. With equally sticky grip on roots, rocks, and off-kilter sidewalks, their skid-resistant outsole and supportive suede collar will keep you sure-footed in anything you’ll face this fall. MSRP: $170. Chacos.com // (Justin Skay)