For a dress that's got some structure while being wildly comfortable, the drop waist style is definitely our go-to. Keep the schoolgirl theme going with ankle socks and a crossbody bag.
Sea Pique Jersey and Perforated Cotton Combo Dress, $414, available at Shopbop.
Styled with Whit Canteen Bag, $348, available at Eaton Trading Co., Alejandro Ingelmo Kennedy Loafers, $475, available at Alejandro Ingelmo, Triwa Beige Chevron Lomin Watch, $190, available at Triwa, and Monica Sordo cuff.
Modeled by Olga Kubrak at Major; Styled by Haley Loewenthal; Hair and Makeup by Bethany Brill; Set Design by Marie-Yan Morvan.