LEFT: Dennis Basso hazel sable jacket ($35,000) and brown cashmere embroidered pants ($2,100) at Dennis Basso, 980 North Michigan Avenue. Chris Benz orange silk-chiffon Amanda shirt ($795) at Blake, 212 West Chicago Avenue. Julie Baker Design yellow-gold locket ($4,445) and handmade yellow-gold chain ($5,720) at Sabbia, 106 East Oak Street. Lambertson Truex wheat python Tori bag ($2,995), by special order at Saks Fifth Avenue, 700 North Michigan Avenue. On eyes: Bobbi Brown Stonewashed Nudes palette ($50) at Bloomingdale’s, 900 North Michigan Avenue. On face: Giorgio Armani Crema Nera ($225) at Saks Fifth Avenue. RIGHT: Oscar de la Renta fuchsia sponge-crepe column gown with open back and black satin belt ($4,950) at Nordstrom, 55 East Grand Avenue. Armenta yellow-gold gypsy hoop earrings with Japanese seed pearls ($1,680) at Manny B& Company, 875 North Michigan Avenue. Tod’s black satin clutch ($795) at Tod’s, 121 East Oak Street. Jimmy Choo black velvet China sandals ($645) at Jimmy Choo, 63 East Oak Street. On lips: Bobbi Brown Shimmer lip-gloss in Stonewashed Nude ($19) at Bloomingdale’s.

Eia Millinery Design grass-green velour-felt Cloche Verte with petersham ribbon trim ($350), by appointment only at Eia Millinery Design, 1620 West Nelson Street; 773-975-5959. Yves Saint Laurent navy felted-wool coat ($2,260), black ribbed-silk unitard ($1,350), and black patent leather Tribute pumps ($660), all at Yves Saint Laurent, 51 East Oak Street. Cole Haan cranberry semiglazed leather Aerin convertible tote bag ($450) at Cole Haan, 673 North Michigan Avenue.

LEFT: Martin Grant black puff bouclé coat with glass buttons (about $1,720) at Barneys New York, 25 East Oak Street. Wolford black opaque nylon-blend tights ($42) at Wolford, 54 East Oak Street. Tod’s black pony-hair boots ($695) at Tod’s. RIGHT: Proenza Schouler black felt hat ($625) and multicolor pleated chiffon dress ($3,545) at Ikram, 873 North Rush Street. Hue navy-blue nylon-blend tights ($9) at Carson Pirie Scott, Edens Plaza, Wilmette. Cole Haan putty patent leather Ambrose Air pumps ($275) at Cole Haan.

LEFT: Roberto Cavalli brown-print silk dress ($4,495) at selected Neiman Marcus stores. Armenta granulated yellow-gold chain neck- lace ($3,160) and wheat yellow-gold chain necklace ($2,300) at Manny B & Company. Dennis Basso brown metallic tweed coat with sable trim ($5,500) at Dennis Basso. Hue navy-blue nylon-blend tights ($9) at Carson Pirie Scott. Cole Haan tan leather Melinda Air Mary Jane pumps ($295) at Cole Haan. RIGHT: Cynthia Rowley forest-green wool hat ($200) at Cynthia Rowley, 808 West Armitage Avenue. Ralph Lauren brown-and-silver cashmere-and-wool A-line coat ($2,998), chocolate cashmere-and-jersey turtleneck ($1,498), and chocolate cashmere-and-jersey circle skirt ($1,298), by special order at Ralph Lauren, 750 North Michigan Avenue. Diana Broussard sterling-silver three-strand necklace ($465) at Neapolitan, 715 Elm Street, Winnetka. Mark Gill chocolate sheared-mink clutch ($1,900) at Elements, 102 East Oak Street. Pottery Barn photographer’s tripod floor lamps at potterybarn.com.

Nina Ricci chartreuse satin strapless gown ($5,790) and chartreuse ostrich-feather and paillette embroidered silk-gauze jacket ($20,000) at Ikram. Di Modolo diamond-and-gold Favola ring ($7,200) at Saks Fifth Avenue and selected Neiman Marcus stores. Escada plum satin heels ($690) at Escada, 840 North Michigan Avenue. Emelie’s chaise, 704-982-6324 for retail locations.

3.1 Phillip Lim sand cashmere two-tone box jacket ($750) at Jake, 939 North Rush Street and 3740 North Southport Avenue, Chicago, and 565 Lincoln Avenue, Winnetka. Sevan amethyst, sterling-silver, and yellow-gold cocktail ring ($9,778) at Manny B & Company.

LEFT: Eia Millinery Design black velour-felt Cloche Fendue with charcoal leather brim and navy petersham trim ($360), by appointment only at Eia Millinery Design. Louis Vuitton blue-gray knitted angora tunic (about $1,545), long silver silk-radzimir shirt (about $1,930), and black wool-tricotine slim pants ($1,159), all at Louis Vuitton, 919 North Michigan Avenue. Tod’s black pony-hair boots ($695) at Tod’s. RIGHT: J. Mendel black wool coat with mink sleeves ($8,500) at J. Mendel Boutique, 919 North Michigan Avenue. Derercuny oyster silk-chiffon blouse ($749) and silver silk-jacquard dress ($1,206) at Neiman Marcus, 737 North Michigan Avenue. Andrew Gn black suede high-heel boots with bows (price on request), by special order at Nordstrom.

Eia Millinery Design brick-red and bottle-green French velour-felt hat with navy petersham trim ($450), by appointment only at Eia Millinery Design. Gucci black wool coat with astrakhan detailing ($2,995) and oxblood cashmere turtleneck ($755), by special order at Gucci, 900 North Michigan Avenue. Armenta yellow-gold and oxidized sterling-silver Midnight earrings with Japanese seed pearls ($1,910) at Manny B & Company.

LEFT: Andrew Gn jet-black sequined silk bolero (about $5,900), by special order at Nordstrom and Neapolitan. Chaiken black organza double-cowl blouse (price on request) at Helen Yi, 1645 North Damen Avenue. Eskell black polyester-blend Ashby high-waisted pants ($276) at Eskell, 953 West Webster Avenue. Lambertson Truex zebra-print calf hair and python Marilyn handbag ($2,995), by special order at Ikram. Jimmy Choo black nappa and patent leather Relax shoes ($595) at Jimmy Choo. Diana Broussard sterling-silver cuff with multicolored pearls ($465) at Neapolitan. RIGHT: Giambattista Valli charcoal-and-yellow graphic-print wool-crepe trench coat, belt not shown ($4,050), and black stretch silk-knit turtleneck ($625) at Blake. Louis Vuitton black leather pants (about $3,220) at Louis Vuitton. Vicente Agor diamond-and-gold leaf bracelet ($9,000) at Saks Fifth Avenue. Claudia Ciuti bronze-and-steel metallic leather heels with tuxedo bow detail ($276), to order at neimanmarcus.com.

LEFT: J. Mendel gray wool-and-silk faille dress with silver-fox trim ($4,200) at J. Mendel Boutique. Hanii Y black cropped cotton-blend jacquard jacket ($462) at Jake. Di Modolo gold Quadria bracelet with diamond accents ($11,900), by special order at selected Neiman Marcus stores. RIGHT: Alessandro dell’Aqua white viscose-and-cotton jacket with sleeves trimmed in goat hair ($1,650); white turtleneck sweater in wool, alpaca, and acrylic ($600); and white viscose slim trousers ($1,275), all at Blake. Escada white leather hobo bag with gold detailing ($1,250) at Escada. Cole Haan black patent leather Dayla Air Mary Jane heels ($295) at Cole Haan.

Photography by Brian Doben