LEFT: MARC JACOBS tank top ($995) and skirt ($1,100), at Marc Jacobs, 11 East Walton Street (opening soon). MARLAINA STONE necklace ($1,600), at She Boutique, 483 Central Avenue, Highland Park. VAN CLEEF & ARPELS earrings ($61,000), ribbon ring ($33,900), and large ring ($10,400), at Van Cleef & Arpels, 636 North Michigan Avenue. RIGHT: CÉLINE jacket ($2,800), blouse ($1,200), and skirt ($1,400), at Ikram, 873 North Rush Street; and Blake, 212 West Chicago Avenue. PALOMA PICASSO FOR TIFFANY & CO. necklace ($850), at Tiffany & Co., 730 North Michigan Avenue. PRETTY LITTLE THING earrings ($42), at Eskell, 1509 North Milwaukee Avenue. HEATHER B. MOORE large ID tags and chain ($5,085) and jumbo ID tags and chain ($8,225), at Virtu, 2034 North Damen Avenue.

Photography: Sean Kennedy Santos

Producer: Gabrielle Fitzgerald
Stylist: Stacey Jones
Models: Jessica Pitti/IMG Models, Flo Gennaro/Supreme Management
Makeup: Hung Vanngo/The Wall Group
Hair: Seiji/The Wall Group
Styling Assistants: Stephanie Soong, Heidi Grunwald

LEFT: MARIA PINTO top ($1,350) and camisole ($285), at Maria Pinto, 135 North Jefferson Street. DENNIS BASSO skirt ($5,000), at Dennis Basso, 980 North Michigan Avenue. SILVIO BETTERELLI FOR FURLA TALENT HUB clutch ($575), at Furla, 1211 West Webster Avenue and 106 East Oak Street. RACHEL LEIGH cuffs ($326 each) and necklace ($188), at W Hotel Chicago-Lakeshore, 644 North Lake Shore Drive. JIMMY CHOO shoes ($495), at Jimmy Choo, 63 East Oak Street. RIGHT: LOUIS VUITTON jacket (about $2,374), denim jacket (about $1,197), shorts (about $507), and boots ($1,580), at Louis Vuitton, 919 North Michigan Avenue. TULESTE MARKET necklace ($130), at Krista K, 3458 North Southport Avenue. JIMMY CHOO bag ($2,995), at Jimmy Choo. LULU FROST large bracelet ($380), small bracelet ($360), and earrings ($130), at Simone’s Boutique, 1060 Gage Street, Winnetka. RACHEL LEIGH cuff ($149), at W Chicago–Lakeshore.

Photography: Sean Kennedy Santos

Producer: Gabrielle Fitzgerald
Stylist: Stacey Jones
Models: Jessica Pitti/IMG Models, Flo Gennaro/Supreme Management
Makeup: Hung Vanngo/The Wall Group
Hair: Seiji/The Wall Group
Styling Assistants: Stephanie Soong, Heidi Grunwald

LEFT: VERSUS dress ($995), at Blake. VERSUS bag ($595), at select Versace boutiques. EXTASIA FOR MATERIAL POSSESSIONS intaglio necklace ($165), MARGARET ELLIS FOR MATERIAL POSSESSIONS chain necklace ($605), and JADE TRIBE FOR MATERIAL POSSESSIONS cuff ($58), at Material Possessions, 704 North Wabash Avenue and 954 Green Bay Road, Winnetka. GIANVITO ROSSI sandals ($730), at Blake. RIGHT: J. MENDEL dress ($2,850), at J. Mendel, 919 North Michigan Avenue. BRUNO LAURENZANO FOR FURLA TALENT HUB clutch ($525), at Furla. EXTASIA FOR MATERIAL POSSESSIONS teardrop necklace ($170) and JUST JULES FOR MATERIAL POSSESSIONS locket necklace ($660), at Material Possessions. COACH flats ($168), at Coach, 625 North Michigan Avenue and other locations.

Photography: Sean Kennedy Santos

Producer: Gabrielle Fitzgerald
Stylist: Stacey Jones
Models: Jessica Pitti/IMG Models, Flo Gennaro/Supreme Management
Makeup: Hung Vanngo/The Wall Group
Hair: Seiji/The Wall Group
Styling Assistants: Stephanie Soong, Heidi Grunwald

MAXMARA trench coat, skirt, and belt (prices on request), at MaxMara, 900 North Michigan Avenue. BURBERRY sweater ($450), similar styles at Burberry, 633 North Michigan Avenue. TED ROSSI FOR MATERIAL POSSESSIONS cuff ($175) and CAROLINA FOR MATERIAL POSSESSIONS necklace ($185), at Material Possessions.

Photography: Sean Kennedy Santos

Producer: Gabrielle Fitzgerald
Stylist: Stacey Jones
Models: Jessica Pitti/IMG Models, Flo Gennaro/Supreme Management
Makeup: Hung Vanngo/The Wall Group
Hair: Seiji/The Wall Group
Styling Assistants: Stephanie Soong, Heidi Grunwald

LEFT: DONNA KARAN dress ($2,595), similar styles at Nordstrom, 55 East Grand Avenue. ALTUZARRA bustier (price on request), similar styles at Ikram. TOD’S bag ($3,025), at Tod’s, 121 East Oak Street. MARLAINA STONE necklace ($3,500), at She Boutique. CARTIER mother-of-pearl ring ($1,300), orchid ring ($8,100), bracelet ($14,600), and earrings ($11,200), at Cartier, 630 North Michigan Avenue. RIGHT: VIONNET blazer ($1,593), at Blake. ANDREW GN pants ($1,255) and belt ($220), at Nordstrom; and Neapolitan, 715 Elm Street, Winnetka. SIMONE studded dress ($928), at She Boutique. DAVID YURMAN necklace ($1,100), bracelet ($460), and ring ($850), at David Yurman, 40 East Oak Street. COACH bag ($1,000), at Coach.

Photography: Sean Kennedy Santos

Producer: Gabrielle Fitzgerald
Stylist: Stacey Jones
Models: Jessica Pitti/IMG Models, Flo Gennaro/Supreme Management
Makeup: Hung Vanngo/The Wall Group
Hair: Seiji/The Wall Group
Styling Assistants: Stephanie Soong, Heidi Grunwald

FRONT: VERSACE jacket ($2,250) and pants ($900), at Barneys New York, 15 East Oak Street. DAVID YURMAN prasiolite ring ($1,350), blue topaz ring ($1,650), cuff ($1,100), round ring ($2,850), long pendant necklace ($1,695), and chunky chain necklace ($4,100), at David Yurman. PALOMA PICASSO FOR TIFFANY & CO. earrings ($7,150), at Tiffany & Co. JIMMY CHOO shoes ($1,095) and bag ($1,150), at Jimmy Choo. BACK: FENDI dress and belt ($4,550) and heels ($1,595), at Neapolitan; and Neiman Marcus, 737 North Michigan Avenue. ERIN GALLAGHER FOR MATERIAL POSSESSIONS pearl necklace ($748), at Material Possessions. CARTIER necklace ($30,800), at Cartier. TIFFANY & CO. bracelet ($875), at Tiffany & Co.

Photography: Sean Kennedy Santos

Producer: Gabrielle Fitzgerald
Stylist: Stacey Jones
Models: Jessica Pitti/IMG Models, Flo Gennaro/Supreme Management
Makeup: Hung Vanngo/The Wall Group
Hair: Seiji/The Wall Group
Styling Assistants: Stephanie Soong, Heidi Grunwald