These dolled-up penny loafers are stylish with tailored trousers or when playing against type with sporty separates or a girlie dress.
Shop the Look: Fleece and leather pullover, Love Zooey, $189; lovezooey.com. Cotton-wool-viscose shorts, Burning Torch, $225; 310-399-1920. Rope, metal, and enamel paint bracelet, Orly Genger by Jaclyn Mayer, $125; jaclynmayer.com. Rhinestone and antiqued silver plated cuff, Giles & Brother, $225; gilesandbrother.com. Leather pumps, Tommy Hilfiger, $89; piperlime.com.Read MoreLess