Sub-zero temps don’t mean you have to abandon all sense of style. Just be smart about winter investments. For bitingly cold weather, break out the Bentley of puffy outerwear: Moncler. Too expensive? Just opt for a long puffer with a belted waist to avoid looking like the abominable snowman. For lighter snowfall, choose Isabel Marant’s ankle-high boots—they’re lined in shearling, so feet will stay toasty, and a treaded rubber sole will help you stay upright in icy conditions. Plus, you won’t have to deal with clunking around in unwieldy snow boots once you’re inside. Layer a graphic necklace over a tunic-style sweater, shimmy into a pair of skinnies, and be sure to bring some pop-top gloves along—arguably winter’s smartest transition piece.