Tod’s brandy calfskin Benji Media satchel ($1,200) at Tod’s, 121 East Oak Street.
DKNY leather peep-toe Britney flats ($195) at selected DKNY stores.
Tommy Hilfiger peach-and-white cotton argyle sweater ($54) and cream twill Bermuda shorts ($49) at Carson Pirie Scott State Street.
Cynthia Steffe pixilated-stripe crochetedbib dress ($350) at Lillie Alexander, 197 East Westminster Road, Lake Forest.

Derek Lam spearmint laundered-satin blouse with organza trim ($890) and black cotton-and-Lycra poplin skirt ($650) at Barneys New York, 25 East Oak Street.

J. Crew navy washed-sateen jacket with gold buttons ($118), white cotton shirt with three-quarter-length sleeves ($48), and striped cotton skirt ($88), all at selected J. Crew stores.

A.P.C. cream textured knee socks ($44) at Penelope’s, 1913 West Division Street.
A.P.C. black crocheted beret ($76) at Penelope’s.

Schumacher blue-striped wool sweater with crocheted collar ($355), brown cotton sleeveless safari shirt ($245), and cotton print Daydream skirt ($395), all at Frannie, 808 Elm Street, Winnetka

Neal Sperling fig-and-natural cotton striped T-shirt ($195), striped cotton scarf ($98), and vanilla nylon cotton skirt ($345), all at Blake, 212 West Chicago Avenue.