1 Jil Sander multicolored beaded pumps ($1,295) at Blake, 212 West Chicago Avenue.

2 Gucci black suede booties with stud detailing ($995) at Gucci, 900 North Michigan Avenue.

3 Cynthia Rowley black leather pumps with fox-fur detailing ($550) at Cynthia Rowley, 1653 North Damen Avenue.

4 Prada brown leather platform pumps with ruffle detailing ($750), similar styles available at Prada, 30 East Oak Street.

5 Chloé gray leather stiletto booties with leaf appliqué ($1,495) at Blake.

Photography: Alex Cao