1Streamline Your Base
Hellin Kay Resist the initial urge to grab the thickest, nubbiest pieces in your closet; a long-sleeve tee worn over skinny pants serves as a sleek base layer. Pro tip: Pants > opaque tights, since "tights are never thick enough in the dead of winter," Duprie says. "Cigarette trousers provide the same look with added warmth."
Old Navy Relaxed Boat-Neck Tee in Navy Stripe, $8.97, oldnavy.com; Old Navy The Long Pixie Pants in Black Jack 3, $36.94, oldnavy.com
2Insulate Your Feet
Hellin Kay Pull a thick pair of knee-high socks on over your pants.While their purpose is more function than fashion, choosing a fun print can't hurt. "It adds a touch of personality to your outfit—even if you're the only one that sees them," Duprie says.
Old Navy Printed Boot Socks, $6, oldnavy.com
3Double Up On the Bottom
Hellin Kay The skirt-over-pants trend is easy to pull off. Just watch the proportions: A figure-flattering full-skirted mini that hits a few inches above the knee shows off just enough leg, while acting as an additional buffer between you and the frigid air.
Old Navy Fit and Flare Skirt in Heather Grey, $13.50, oldnavy.com
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4Pile on a Sumptuous Sweater
Hellin Kay What would winter layering be without a plush pullover? This cashmere-blend knit skims the frame without appearing too bulky. Duprie recommends one that's 1) cable-knit for added dimension, and 2) cropped just above the waist so it reveals the striped tee underneath.
Club Monaco Meera Cable-Knit Sweater in Pale Heather Grey, $149.50, clubmonaco.com
5Time to Boot Up
Hellin Kay Flat over-the-knee boots are the most fashionable winter-approved footwear. They elevate any outfit while covering even more surface area.
Stuart Weitzman Lowland Boot in Black Suede, $798, stuartweitzman.com
6Top it Off With a Cool Coat
Hellin Kay In lieu of your trusty parka or longline overcoat, make a statement with an insulated bomber jacket. "Look for something that's incredibly warm but somewhat short," Duprie says. "You want to show off your outfit without covering up any of the layers."
Old Navy Plaid Wool-Blend Bomber Jacket in Navy Plaid, $35, oldnavy.com
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7Add a Standout Scarf
Hellin Kay A layered winter look isn't complete without a chunky knit slung around the neck. (For the record, bulk is a good thing here.) Duprie recommends choosing a brightly colored circle scarf that you can wrap two or three times; that way, it becomes your outfit's main accessory.
Old Navy Chunky-Knit Infinity Scarf in Apple of My Eye, $8, oldnavy.com
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