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This fall, the smart money is on penny loafers as a classically chic casual look. Ellen Tracy's Relay sees this traditional silhouette in a stylish new light, thanks to glossy patent leather finishes and leather with leopard-print haircalf detailing.

Wind and winter weather can't stop you. Lace up these soft, durable and supportive Windy boots by Naturalizer, featuring a wide calf design, for stylish protection from the elements.

Classic fall style. Style&co.'s Ryder boots feature buckled straps around the ankle and top of shaft and a small, walkable wedge heel.

GUESS by Marciano's Raya booties feature faux shearling along the inside. Cuffed or uncuffed, these cute booties, with their major platform and heel, will add mega intensity to your look.