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I'm always trying to find a pair of boots which not only are fit for winter, but also look polished enough to wear at work. These Cole Haan Air Stanton Chelsea Boots ($248) are perfect for that outdoor/indoor transition . They are completely waterproof and feature a lug sole to make sure you don’t slip on those icy sidewalks, yet their sleek profile makes them appropriate to wear with everything from a suit to jeans.

— Robert Khederian, fashion editorial assistant

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