Gear wonks like to debate the origin of soft shells. Let us direct you to the Mackinaw Cruiser, which has remained virtually unchanged since it debuted in 1914. Like our favorite softies, this 100 percent wool jacket is weather-resistant and tougher than dirt. It fits closely because you buy it like a suit—it's available in ten different sizes. There's even a large "cruiser" pocket on the back, accessible from either side, that's big enough to hold everything from maps to lunch. The understated and classic styling, of course, is not up for debate.

Filson Mackinaw Cruiser $275 filson.com