Prada vanilla cotton, mohair, and wool faux-fur cardigan ($980) at Prada, 30 East Oak Street. Bottega Veneta black washed-silk-crepe dress ($5,380) at Bottega Veneta, 800 North Michigan Avenue, and Ikram, 873 North Rush Street. Bottega Veneta black leather belt ($590) at Bottega Veneta. Isabella Fiore bronze satchel ($650), similar styles at Bloomingdale’s, 900 North Michigan Avenue. Jimmy Crystal Swarovski crystal zebra ring ($24) at Bag Plaza Corporation, 4533 North Clark Street.

Marni black washed-viscose long-sleeved shirt ($648) and black polyurethane skirt ($486) at Blake, 212 West Chicago Avenue. Chanel black-and-gold acetate, metal, and resin Paris Monte Carlo cuff ($1,650) and black-and-gold metal, stone, and Glasstone necklace ($1,895) at selected Chanel boutiques. Kristina Fine Jewelry diamond, blue topaz, sapphire, and white-gold ring ($8,000) at C. D. Peacock, 520 North Michigan Avenue. Tod’s red patent leather D-Bag Grande ($1,795) at Tod’s, 121 East Oak Street. DKNY black opaque nylon-blend tights ($14) at Bloomingdale’s. Jimmy Choo navy watersnake and kid leather Disco sandals ($750) at Jimmy Choo, 63 East Oak Street.

Y & Kei black-and-white acetate jumpsuit ($1,450), by special order at Ultimo, 114 East Oak Street. Vilaiwan freshwater-pearl, crystal, and satin-ribbon necklace ($390) at Greer, 1657 North Wells Street.

Brian Reyes silver silk-blend dress ($2,245), by special order at Neapolitan, 715 Elm Street, Winnetka. Salviati red Venetian blown-glass Caviale-R necklace ($550), to order at salviati.com.

Comme des Garçons black-and-white wool checked jacket ($1,490) and gray leggings with attached hands and dropped inseam ($295), similar styles at Saks Fifth Avenue, 700 North Michigan Avenue. Jimmy Crystal large oval teal Swarovski crystal ring ($38) at Bag Plaza Corporation. French & French stingray-skin Boston Bag ($560) at Chelli Chique Accessory Boutique, 120 North York Street, Elmhurst. Chloé black leather and wood slingback heels (price on request) at Blake.

Rodarte moss-green wool jacket ($4,830) and moss-green wool bubble skirt ($3,026) at Ikram. Chanel Paris Monte Carlo necklace in metal, Glasstone, and resin ($1,580) and bracelet in metal, stone, and Glasstone ($2,150) at selected Chanel boutiques. Jimmy Crystal Swarovski crystal leopard bangle bracelet ($80) at Bag Plaza Corporation. Furla mourmansky fur Virginie bag ($675) at Furla, 106 East Oak Street and 1211 West Webster Avenue. Coach patchwork velvet Diedra peep-toe heels ($268) at Coach, 625 North Michigan Avenue and 900 North Michigan Avenue.

Yohji Yamamoto long black silk ruffled dress ($11,690) and black wool pants ($900) at Ikram. MaxMara black wool military jacket ($1,305) at MaxMara, 900 North Michigan Avenue. Derercuny black resin flower necklace ($250) at luisaviaroma.com. Stuart Weitzman black suede studded Bulletin pumps ($280) at Stuart Weitzman, 900 North Michigan Avenue.

Giambattista Valli black wool and silk-radzimir short-sleeved ruffled jacket worn backwards ($1,650) and black wool and silk-radzimir slim side-zip pants ($660) at Blake. Derek Lam gold silk-lamé long-sleeved pleated dress ($1,990), by special order at Helen Yi, 1645 North Damen Avenue. Tanya Farah chunky pearl bracelet ($350) at Sydel & Sydel Jewelry, 208 South LaSalle Street. Cynthia Rowley shimmering nylon-blend tights ($54) and brown printed-suede platform pumps ($445) at Cynthia Rowley, 808 West Armitage Avenue.

Givenchy midnight-blue astrakhan-and-fox fur vest ($15,340) at Blake. Louis Vuitton blue round-collar leather shirt (about $3,735) and blue wool-lamé New Look skirt (about $2,060) at Louis Vuitton, 919 North Michigan Avenue. Bottega Veneta long black shearling gloves ($820) at Bottega Veneta. MaxMara black leather pumps with metallic heels ($470) at MaxMara.

Alexander McQueen green silk-and-polyester cowl-neck dress ($4,025) at Ikram. Marni black-and-green resin and horn disk necklace ($681) and dark-anthracite open-toe cotton tights ($96) at Blake. Tod’s red-and-brown, brown-and-gold, and black-and-gold calfskin bracelets ($225 each) at Tod’s. Kristina Fine Jewelry yellow opal and yellow-gold ring ($2,800) and yellow sapphire, citrine, diamond, and white-gold ring ($2,405) at C. D. Peacock. Giuseppe Zanotti Design black patent leather gladiator sandals with redwood platforms ($650) at Josephine, 1405 North Wells Street.

Photography by Tom Corbett