Piazza Sempione citrine wool-blend sweater ($848) at Saks Fifth Avenue, 700 North Michigan Avenue. Cynthia Rowley aubergine silk-and-nylon-blend petal cape worn as skirt ($525) at Cynthia Rowley, 808 West Armitage Avenue. BCBG Max Azria black leather round-toe, zip-up calf Nikkas boots with velvet embellishment ($325) at BCBG Max Azria, 113 East Oak Street. Betsey Johnson green leather Viva La Betsey bag ($275) at Betsey Johnson, 2120 North Halsted Street, and Lord & Taylor, Westfield Old Orchard, Skokie. Hue peacock-blue opaque nylon-blend tights ($11) at Nordstrom, 55 East Grand Avenue. On eyes: Chanel Irréelle Duo in Lotus and Cactus ($39) at Chanel, 935 North Michigan Avenue. On lips: Les 4 Camélias de Chanel lip palette ($65) at Chanel.

Lanvin red washed-silk-satin three-quarter-sleeve round-neck dress ($3,200), by special order at Barneys New York, 25 East Oak Street. Fogal purple opaque nylon-blend tights ($39) at Fogal, 900 North Michigan Avenue. Coach red suede Kayln wedges ($178) at Bloomingdale’s, 900 North Michigan Avenue.

Giuliana Teso red-fox coat ($10,800), by special order at selected Neiman Marcus stores. Mint Jodi Arnold Prussian-blue jeweled shift dress ($430) at Krista K, 3458 North Southport Avenue. Fogal orange opaque nylon-blend tights ($39) at Fogal. Dries Van Noten light-gray leather ankle boots ($636) at Blake, 212 West Chicago Avenue.

Thakoon blue double-duchesse cocoon coat ($1,750), by special order at Ikram, 873 North Rush Street. Doo.Ri canary sequined top ($3,300) at Jake, 3740 North Southport Avenue and 939 North Rush Street, Chicago, and 565 Lincoln Avenue, Winnetka. Louis Vuitton red leather pleated skirt (about $3,735) at Louis Vuitton, 919 North Michigan Avenue. Judith Ripka yellow-gold Ambrosia bracelet ($28,000) and yellow-gold Lola ring ($5,200) at Judith Ripka, 129 East Oak Street. THIS PAGE: Ermenegildo Zegna charcoal-gray double-breasted wool suit ($1,995) and blue-printed silk tie ($140) at George Greene, 49 East Oak Street, and Ermene-gildo Zegna, 645 North Michigan Avenue. Lorenzini white cotton shirt ($310) at George Greene.

Jean Paul Gaultier teal silk blouse ($1,220) and teal silk skirt ($4,125) at Perlie, 897 Green Bay Road, Winnetka. BCBG Max Azria mulberry wool-blend cardigan ($178) at BCBG Max Azria. MaxMara yellow wool military jacket ($1,115) at MaxMara, 900 North Michigan Avenue. Coach caramel leather Hamptons Vintage carryall ($798) at Coach, 625 North Michigan Avenue and other locations. DKNY black opaque nylon-blend tights ($14) at Bloomingdale’s. Furla red suede and patent leather Virginie pumps ($280) at Furla, 106 East Oak Street and 1211 West Webster Avenue.

Jil Sander violet paper-wool cape coat ($1,830) at Blake. Oscar de la Renta fuchsia embroidered silk-faille sleeveless dress ($3,950) at Nordstrom. Hermès blue leather Paris Bombay bag ($4,200) at Hermès, 110 East Oak Street. Fogal orange opaque nylon-blend tights ($39) at Fogal.

Ermenegildo Zegna charcoal-gray double-breasted wool suit ($1,995) and blue-printed silk tie ($140) at George Greene and Ermenegildo Zegna. Lorenzini white cotton shirt ($310) at George Greene. Maria Pinto ocean-blue shibori overdyed wool Tallulah coat ($2,600) at Maria Pinto Atelier, 2211 North Elston Avenue. Zac Posen aubergine wool chintz Iris jacket ($1,900), deep-purple stretch-viscose Iris blouse ($900), and aubergine wool chintz Tuxedo skirt ($990), all at Neapolitan, 715 Elm Street, Winnetka.

Photography by David Anthony