Proenza Schouler navy chiffon-and-sequin sleeveless pieced dress ($5,525), Rick Owens gray cashmere tights ($1,225), and Halston Bree boots in Halston gray suede ($995), all at Ikram.



Yves Saint Laurent extra-fine wool turtleneck ($625), Tokyo silk asymmetrical jacket with peplum ($2,400), and Tokyo silk high-waisted front-seam skirt ($1,400), all in black at Neapolitan, 715 Elm Street, Winnetka. Yves Saint Laurent ribbed cashmere tights from a selection by the designer (price on request) at Yves Saint Laurent, 51 East Oak Street. Jimmy Choo Erica black suede booties ($1,395) at Jimmy Choo, 63 East Oak Street.



Jil Sander Balzac pearl wool-felt jacket ($2,345) and black stretch-wool boy pants ($750) at Jil Sander, 40 East Oak Street, and Blake, 212 West Chicago Avenue. Jimmy Choo Helena black patent leather boots ($995) at Jimmy Choo.



Ohne Titel black lightweight-wool suit with single-breasted side-button jacket and skinny dress pants ($2,050) at Ikram, 873 North Rush Street. Jimmy Choo Kindle heels in red patent leather ($615) at Jimmy Choo.



OPPOSITE: Calvin Klein Night polished razor-cut cashmere jacket ($4,675), sheer molded silk-and-cashmere shirt ($1,315), and wool-crepe pencil trousers ($1,090), all in navy at Macy’s 28 Shop, 111 North State Street, and Saks Fifth Avenue, 700 North Michigan Avenue. Jil Sander black leather ankle-strap pumps ($695) at Jil Sander and Blake.



Halston sheer chiffon cape ($2,495),silk open-back flared  blouse ($995), and silk pull-on pants ($1,125), all in Halston gray at Ikram. Ralph Lauren Arlington black crocodile booties ($5,000) at Ralph Lauren, 750 North Michigan Avenue.



 Rick Owens metallic leather jacket ($5,295) at Ikram. MaxMara gray silk-and-cashmere dress ($995) and black leather ankle boots ($760) at MaxMara, 900 North Michigan Avenue. Martin Margiela oversize beaded clutch in black cotton velvet ($3,295) at Ikram.



Louis Vuitton ecru techno-ribs knit turtleneck ($815), wide periwinkle-gray shaggy-wool skirt ($1,830), cream shaggy-wool structured jacket, and gray-and-black leather wedges, jacket and wedges available in similar styles (prices on request), all at Louis Vuitton, 919 North Michigan Avenue. Yves Saint Laurent ribbed cashmere tights from a selection by the designer (price on request) at Yves Saint Laurent.

Photography: Sean Kennedy Santos Model: Heide Lindgren/ Muse Hair: Lydia O’Carroll using L’oreal infinium makeup: Karen Abitol Photo Styling: Stacey Jones Photo Styling assistant:Heidi Grunwald Producer: gabrielle Fitzgerald Photographed at Trapeze School New York