For fall, I've always been intrigued by the balance of a flirty and floaty skirt worn with a cozy sweater and jacket. It's the equation of showing some leg, but covering up on top that brings a refined element to the look. (If the weather doesn't allow for bare legs, just add thick tights in gray, navy, or black.) To finish the outfit, a chic velvet blazer, metallic menswear-inspired oxfords, and a two-tone carryall lend a preppy edge, but more importantly, they add comfort and functionality.