B. Hartford’s red plaid western shirt on My Life with the Walter Boys

Jackie’s navy contrast polo on My Life with the Walter Boys

Kearney Short-Sleeve Polo Tee by Veronica Beard at Neiman Marcus, $198

Jackie’s gray varsity mini dress on My Life with the Walter Boys

Varsity Twofer Mini Dress by Anthropologie, $39.95 (was $168)

Jackie’s black cropped vest on My Life with the Walter Boys

In Motion Vest by Alo Yoga, $108

Jackie’s navy mini dress on My Life with the Walter Boys

Flutter Sleeve Fit & Flare Sweater Dress by Ted Baker at Nordstrom, $139 (was $295)

Jackie’s cable knit sweater on My Life with the Walter Boys

Cable Cotton Crewneck Sweater by Ralph Lauren at Nordstrom, $148