The Trackhead Winter Boot ($325) is both rugged and casual with eye-catching style. This work-wear inspired footwear by Timberland is made with burnished, waxed and washed brown canvas with brown Horween premium, full-grain leather toe cap and details. The Trackhead Winter Boot features a multi-density EVA footbed for support and comfort, thick wool lining for warmth and rubber Vibram outsole for traction and durability.