1> JIMMY CHOO bag ($2,595), at 63 E. Oak St.

2> STEVE MADDEN booties ($130), at Akira Footwear, 1849 W. North Ave.

3> CYNTHIA ROWLEY booties ($495), at 810 W. Armitage Ave. and 1653 N. Damen Ave.

Photography: Jeff Harris

4> ANTHROPOLOGIE necklace ($158), at Anthropologie, 1120 N. State St.

5> ESCADA wide belt ($350), at Escada, 840 N. Michigan Ave.

6> COLE HAAN belt ($68), at Cole Haan, 673 N. Michigan Ave.

Photography: Jeff Harris

7> GIDIGIO boots ($330), at Florodora Shoes, 348 S. Dearborn Ave.

8> CLUB MONACO messenger bag ($229), at Club Monaco, 900 N. Michigan Ave. and other locations.

9> FURLA hobo bag ($475), at Furla, 106 E. Oak St.

Photography: Jeff Harris