The Lowdown: Heading somewhere potentially chilly and/or wet for the holidays (or heck, live somewhere that’s chilly and/or wet all the time?). There’s nothing that says a fashionista can’t be warm and practical too, especially this fall/winter with all the suede/shearling/ faux-fur boots we’ve seen everywhere. Navigating the dressy/casual line in messy weather can be tricky, but on the whole, protecting yourself from frostbite is job one — so we’d suggest slipping on some trendy but warm and waterproof boots for travel/commuting, and carry a big bag this winter to stow footwear appropriate to your destination as needed. Think you can’t get waterproof warmth AND style all at once? Piperlime proves otherwise, with these incredibly cute boots, under $100 each.