Tart empire waist dress ($210)

Elle Jewelry necklace ($110),

bracelet ($168) and earrings ($62)

Next Door, Brookfield

United Nude Moebieus pump ($199)

Shoo, Milwaukee

Free People tiered dress ($110)

Juliet Jewelry sterling silver earrings ($65) Next Door

Kathleen Van Wagenen bracelet ($30) Jennifer Mog necklace ($89)

Kyle Meyer ring ($40) J. Bird, Milwaukee

Lara Miller Prosper dress ($280) Kate Blake earrings ($25)

Kathleen Van Wagenen bracelets ($30 each)

Jacqueline Jarrot handbag ($349)

J.Bird

United Nude Moebieus pump ($199)

Shoo

Molly empire-waist dress ($154)

Tammy earrings ($38)

I See London, Fox Point

Lara Miller Lupe sweater ($336)

Julie dress ($159) Kelleigh tunic ($373)

Red Engine jeans ($159)

213 Industry belt ($69)

Tammy Spice earrings ($36) J. Bird

John Fluevog Giulia Burgundy Button Booty boot ($269) Shoo

Hartmann Wings traveler ($695) and tote ($475)

Landmark Luggage, Mequon

Dressed to Kill leather jacket ($313)

Ann Ferriday cami ($113)

Pure Color cropped jean ($150) Tammy necklace ($92) and earrings ($38)

Betsy Johnson belt ($85)

I See London

Chie Mi Hara, Kalo boot ($509)

Orla Kiely briefcase ($359) Shoo

R Jean ballerina dress ($123) I See London

Juliet Jewelry necklace ($65) and earrings ($65) Next Door