1 SHELLY LITVAK rutilated-quartz pendant necklace with yellow and white diamonds, red coral fist, and white-gold detailing ($1,200) at Tula, 3738 North Southport Avenue. 2 RELIGION chain-strap and rayon chain-print dress ($170) at Clever Alice, 750 North Franklin Street. 3 YIGAL AZROUËL black-and-gold strapless dress in wool-and-silk jacquard ($1,130) at Nordstrom, 520 North Michigan Avenue. 4 CUFFZ INC. Duchess clutch in silver with keyless-release handcuff ($165) at Plein Aire, 2036 West Division Street. 5 JIMMY CHOO Apple stiletto heels in black satin with crystal detailing ($995) at Jimmy Choo, 63 East Oak Street. 6 WENDY GLEZ Italian lace and silk-charmeuse bra ($84) and thong ($53) at Wildflowers, 1407 North Wells Street. 7 Belabumbum black polyester-and-viscose baby-doll camisole with pearl lace ($50) at Cheeky Fine Lingerie, 658 Central Avenue, Highland Park. 8 MASON BY MICHELLE MASON shantung strapless top in black ($240) at Della Moda, 1780 Green Bay Road, Highland Park. 9 TEVROW+CHASE leopard-print Julia skirt in cotton, acrylic, and polyester ($285) at Ouest, 1063 West Madison Street. 10CHANEL haute couture sunglasses with feathers and organza ($2,450) at selected Chanel boutiques, 800-550-0005.

PHOTOGRAPHY BY JEFF HARRIS (ALL EXCEPT 4, 5, 10)