AK Anne Klein Sport Women's Buttons Ballet Flat

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.

Classic oxfords with a colorful punch. Steve Madden's Jazie oxfords feature brilliant blue soles for a look that screams preppy chic.

Awesome textures for those lower temperatures. Kensie's Boss booties feature a fully lace-up vamp with thick laces and blanket detailing on the sides of the shaft.

The worn-in detail on the tapered toe of Giani Bernini's Allcott boots lends rugged charm to this otherwise polished style.