Photography: Courtesy of vendors
“Statement skirts are big for fall—and this flattering one will mix well with your existing wardrobe.”
Wool skirt, $150, Club Monaco, 1731 N. Damen Ave.
Rag & Bone wool-cotton jacket, $995, shopbop.com
Silk chiffon dress, $17,000, valentino.com
“The wrap front makes this elegant coat as cozy as a blanket.”
Céline cashmere coat, $6,000, Ikram, 15 E. Huron St.
The Row cashmere sweater, $4,490, Barneys New York, 15 E. Oak St.
Alexander Wang silk top, $1,250, and silk peplum-front pants, $820, saksfifthavenue.com
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Balenciaga silver-plated brass cuff, $425, Blake, 212 W. Chicago Ave.
“These beauties will make your legs look miles long. Pair them with a skirt or cropped pants.”
Derek Lam calfskin booties, $875, Saks Fifth Avenue, 700 N. Michigan Ave.
Aged-gold necklace, $750, Tory Burch, 45 E. Oak St.
Croc-print leather clutch, $310, L.K.Bennett, 900 N. Michigan Ave.
Rag & Bone wool sweater with leather trim, $450, Barneys New York
Prorsum wool twill coat, $3,295, Burberry, 633 N. Michigan Ave.
Cotton-wool blazer, $595, and pants, $295, Gant Rugger, 1702 N. Damen Ave.
“This shirt is more versatile than you’d think. Dress it up with a black blazer; wear it with jeans to go casual.”
Dries Van Noten silk shirt, $665, bergdorfgoodman.com
“I love pairing bright pants with neutral shades that are in every man’s wardrobe.”
Wool pants, $630, paulsmith.co.uk/us-en
Leather jacket, $998, AllSaints, 700 N. Michigan Ave.
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“Backpacks are making a major comeback. This one is good-looking and incredibly well priced.”
3.1 Phillip Lim canvas backpack, $30, Target, 1 S. State St.
Vans canvas chukkas, $56, stevenalan.com
A.P.C. tweed hat, $195, usonline.apc.fr
Leather boots, $725, Marc Jacobs, 11 E. Walton St.