Warm to the form of a slouchy cashmere vest from Inhabit ($480; Ami Ami, Deerfield, Ill., 847-940-0669).
Perfect for your neck of the woods: this Aldo Accessories plaid scarf ($18; aldoaccessories.com).
Pair this Imitation of Christ pencil skirt ($225; Albertine, NYC, 212-924-8515) with a ruffles blouse.
Fee stay fashionably warm and dry in lace-up boots from Via Spiga ($275; nordstrom.com).
A red leather Hayden-Harnett bag ($450; haydenharnett.com) is a surefire attention-getter.
With its cropped cut and shawl collar, this Theory wool and cashmere jacket ($595; theory.com for stores) is a ladylike update on a classic.
Top off your cold-weather attire with this fun Simply Vera Vera Wang hat ($35; kohls.com).