Rachel Boesing’s black tie neck blouse and jacket on Sherri

Maria’s red two-piece knit dress on Sherri

Knit 2-in-1 short dress by Maje at Nordstrom, $385

Also available at: Bloomingdales | Neiman Marcus | Maje

Sherri’s white floral print tie neck blouse on Sherri

Harbison Romantic Floral Tie Neck Top by Nordstrom x Harlem's Fashion Row at Nordstrom, $129

Sherri’s striped polo top and skirt on Sherri

Sydney Striped Polo Top by A.L.C. at Bloomingdales, $227 (was $325)

Also available at: Saks Fifth Avenue | Revolve

Sherri’s purple belted dress on Sherri

Mock Neck Belted Pleated Dress by Anna Taylor at Ann Taylor, $169

Sherri’s plaid tweed jumpsuit on Sherri

Tweed Jumpsuit by Aqua at Bloomingdales, $118