For Women

Wool skirt

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

Rag & Bone wool-cotton jacket, $995,



Silk chiffon dress

Silk chiffon dress, $17,000,



Céline cashmere coat

“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

The Row cashmere sweater, $4,490, Barneys New York, 15 E. Oak St.



Alexander Wang silk top

Alexander Wang silk top, $1,250, and silk peplum-front pants, $820,

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Balenciaga silver-plated brass cuff

Balenciaga silver-plated brass cuff, $425, Blake, 212 W. Chicago Ave.



Derek Lam calfskin booties

“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

Aged-gold necklace, $750, Tory Burch, 45 E. Oak St.



Croc-print leather clutch

Croc-print leather clutch, $310, L.K.Bennett, 900 N. Michigan Ave.

NEXT: Menswear »


For Men

Rag & Bone wool sweater with leather trim

Rag & Bone wool sweater with leather trim, $450, Barneys New York



Prorsum wool twill coat

Prorsum wool twill coat, $3,295, Burberry, 633 N. Michigan Ave.



Cotton-wool blazer

Cotton-wool blazer, $595, and pants, $295, Gant Rugger, 1702 N. Damen Ave.



Dries Van Noten silk shirt

“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,



Wool pants

“I love pairing bright pants with neutral shades that are in every man’s wardrobe.”

Wool pants, $630,



Leather jacket

Leather jacket, $998, AllSaints, 700 N. Michigan Ave.

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3.1 Phillip Lim canvas backpack

“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

Vans canvas chukkas, $56,



A.P.C. tweed hat

A.P.C. tweed hat, $195,



Leather boots

Leather boots, $725, Marc Jacobs, 11 E. Walton St.