The North Face Back-To-Berkeley Boot - Men's - $71.97

It would be nice to spend the winter in a sunny, temperate clime (with frequent trips to snowy peaks thrown in), but since most us us aren't that lucky, The North Face created the Men's Back-to-Berkley Boot. And while it may sport a retro West-Coast-y vibe, this is one boot that's ready for old-school, nasty northern winters. Between the PU coating on the ballistic mesh upper, the waterproofing on the suede mudguard, and the Hydroseal waterproof membrane, your feet won't be getting wet this winter. Thanks to 100-gram PrimaLoft Eco insulation, they'll be warm, too. - $71.97