It's a smart idea to invest in some solid boots that can get you through all occasions (dress-up and dress-down) and weather (fair and foul). We could get semantic about it, but the truth is that any Red Wing model will exceed your expectations. What sets apart the Heritage 9156 moc boot, part of the century-old company's Genuine Handsewn range, is the sturdy, traditional moccasin construction. The leather for this made-in-Maine boot is something called Copper Rough & Tough, a thick hide augmented by a beautiful patina. Plus, the cushioned natural rubber sole manages to be durable yet gentler on the feet than your typical lug-soled stompers. [Red Wing Heritage 9156 Moc Boot, $310;]