1 LEIGHELENA cuff ($95), at Gem, 1710 North Damen Avenue.

2 SOÏA & KYO Destiny jacket ($450), by special order at Cinnamon Boutique, 2104 West Roscoe Street.

3 LEIFSDOTTIR blazer ($398), at Bloomingdale’s, 900 North Michigan Avenue.

4 JOIE Alicia tank top ($244), at Krista K, 3458 North Southport Avenue.

5 ELIZABETH AND JAMES Stiletto dress ($545), at Fix, 1101 West Fulton Street; and Roslyn.

6 KATE SPADE Blair flats ($200), at Kate Spade, 56 East Oak Street.

7 FRANK TELL leggings ($1,195), at Sarca, 710 North Wabash Avenue.

8 DEDE satchel ($195), at Florodora, 330 South Dearborn Street.

Photography: Jeff Harris, (5, 6, and Valentino) courtesy of designers