Margaret Josephs’ pink strapless dress on Sherri

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

Sherri’s beige floral dress on Sherri

Floral Long Sleeve Dress by Stine Goya at Nordstrom, $425