1 JIMMY CHOO Lou sunglasses in gray gradient ($295) at Jimmy Choo, 63 East Oak Street. 2 ANANAS Fabina nude crinkled patent leather purse ($360) at Niche, 1566 North Damen Avenue. 3 Nine West short-sleeve satin top with petal detail in champagne ($79) at Carson Pirie Scott, 3333 West Touhy Avenue, Lincolnwood. 4 Loeffler Randall wool suspender skirt in taupe ($260), by special order at Jake, 939 North Rush Street. 5 Blue Notch five-pocket classic slim boot-cut jean in light charcoal wash ($190) at p.45, 1643 North Damen Avenue. 6 USE yellow cotton halter dress with front ruching ($321) at She, 1024 West Armitage Avenue. 7 Dana Rebecca Designs Converse Falcon ring in morganite with diamonds ($4,840) at Marshall Pierce & Company, 29 East Madison Street. 8 Studio 1 a.m. cork cuff ($48) at Green Mango Goods, 5247 North Clark Street. 9 Vince wool-blend half-tie coat in taupe ($285) at Neiman Marcus, 737 North Michigan Avenue. 10 KENNETH COLE Motorway mustard leather bag ($368) at Kenneth Cole, 540 North Michigan Avenue. 11 Cynthia Rowley alpaca teddy wool cardigan ($405) at Cynthia Rowley, 1653 North Damen Avenue.

Photography: Jeff Harris (all except 1, 7)