Ariat, and OluKai—employ impregnated leather for a unique spin on winter-ready protection. The thing is, these don’t look like the rubber-coated winter boots you might be accustomed to.

Like the Skyline Low, though, grip is somewhat limited. Smart, supple leather meets bouncy rubber soles in the pleasingly lightweight Ariat Skyline, surely one of the best-looking walking shoes on ...