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?