Help! What Do I Wear To That? (Cold-Weather Edition)

And with the first sub-50-degree day, the start of "we can really start dressing" season began. But while creative layering, a good coat, and sweaters with big sleeves can rise to most cold-weather occasions, life still finds a way of throwing in a sartorial curveball every now and then. For instance, what do you wear to your S.O.'s family holiday party — when you've never met the parents, let alone celebrated with them before? What about a ski weekend — when you're still unclear on the difference between the bunny trail and the black diamond?

There's no need to break a sweat when you've got Cuddl Duds as a warmth-retaining base layer, and us, to preemptively style pitch-perfect outfits for five of the season's trickiest scenarios. Ahead, see how we've got you covered — in the clothes department, at least.