(1) JONES NEW YORK red silk belted cocktail dress ($170) at selected Carson Pirie Scott stores. (2) SAJA black silk-chiffon top with charmeuse detailing ($205) at Flirt, 3449 North Southport Avenue. (3) LISA FARRELL blue Thai silk Peacock Alley hat with handmade flower and vintage veil ($425) at Ooh-La-La, 441 Central Avenue, Highland Park. (4) SOPHIA AND CHLOE Katherine reproduction Lalique cameo necklace with pearl and gold-filled chain ($495) at Bourdage Pearls, 3530 North Southport Avenue. (5) FIDELITY DENIM silk-denim Tantra jeans ($198) at The Dressing Room, 4635 North Lincoln Avenue. (6) CHULO PONY crimson herringbone tweed blazer with leather cuffs and belt ($315) at Clever Alice, 750 North Franklin Street. (7) BUILT By Wendy silver metallic wool vest ($134) at Penelope’s, 1913 West Division Street. (8) SUSANA MONACO flax boiled-wool mock cape ($396) at Mint Julep, 1013 West Armitage Avenue. (9) TEVROW + CHASE dark-green floral taffeta Aerin dress ($395) at Ouest, 1036 West Madison Street. (10) ISABELLA FIORE black-and-tan embroidered Spanish chenille Heirloom Bloom Celine bag with calf and patent leather trim ($650) at Bloomingdale’s, 900 North Michigan Avenue. (11) STUART WEITZMAN chocolate leather Hampshire lace-up oxford pumps ($285) at Stuart Weitzman, 900 North Michigan Avenue.
Photography by Jeff Harris (except 4, 10, 11)