1 ESCADA purple satin heels ($650) at Escada, 840 North Michigan Avenue. 2 GUESS BY MARCIANO Carrie black leather heels ($90) at Carson Pirie Scott, 1 South State Street. 3 GUCCI black-and-white leopard-print satin peep-toe pumps with crystal horse bit ($595) at Gucci, 900 North Michigan Avenue. 4 and 5 STUART WEITZMAN Fever heels in wildcat and gunmetal patent leather ($250) at Stuart Weitzman, 900 North Michigan Avenue. 6 MANOLO BLAHNIK Albita white patent leather open-toe slingbacks ($635) at Neiman Marcus, 737 North Michigan Avenue.

photograph by alex cao