Edited by Stephanie Soong

1 CLUB MONACO Harriet gray-and-white cotton-and-elastane coat ($249) at Club Monaco, 900 North Michigan Avenue; 1731 North Damen Avenue; 2206 North Halsted Street; and 1074 Northbrook Court, Northbrook.

2 SAJA gray silk-charmeuse dress ($499) at Les Dress, 1741 West Division Street.

3 ABIGAIL GLAUM-LATHBURY Aseel sand stretch-cotton jacket ($385) at p.45, 1643 North Damen Avenue.

Photography: Jeff Harris (Except 4, 9, 12)

4 FURLA Bouganville black leather and gray snakeskin pumps ($365) at Furla, 106 East Oak Street and 1211 West Webster Avenue.

5 BUILT BY WENDY black cotton-canvas skirt ($149) at Penelope’s, 1913 West Division Street.

6 HELMUT LANG silver silk cropped pants ($290) at Hejfina, 1529 North Milwaukee Avenue.

Photography: Jeff Harris (Except 4, 9, 12)

7 LAURIE B. Swing gray cotton-and-cashmere cardigan ($202) at Clothes Minded, 1735 North Damen Avenue.

8 GRÓA BY GRO ABRAHAMSSON Mitte black tie-dyed linen-and-viscose skirt ($289) at Tula, 3738 North Southport Avenue.

9 TORY BURCH black-and-ivory resin cuffs ($150 each) at Tory Burch, 66 East Walton Street.

Photography: Jeff Harris (Except 4, 9, 12)

10 MAXMARA white leather crocodile-embossed bag ($1,340) at MaxMara, 900 North Michigan Avenue.

11 MATTHEW AMES Maki black-and-white tussah-silk dress ($955) at Helen Yi, 1645 North Damen Avenue.

12 BETTYE MULLER Katy stone linen espadrilles ($170) at Perchance, 3512 North Southport Avenue.

Photography: Jeff Harris (Except 4, 9, 12)