I've said it before (here) and I'll say it again...
There is a necessity for warmth during these Chicago winters. Are you all screaming, "Duh!" to yourself right now? But who says it can only happen by wearing a down filled sleeping bag with sleeves? Exactly. Try layering a few thin items with a few thick ones and of course, sweater tights and Hunters.
Recreate my look:
LOFT skirt (similar), Cuddl Duds long sleeve tee, denim shirt, LOFT sweaters (similar), J.Crew vest (similar), HUE tights, gray Hunters, Uniqlo beanie (similar), Tory Burch sunglasses, Nars Red Lizard lipstick


