Marc Jacobs Printed Wool Bermuda Shorts.
$895, net-a-porter.com — TIP: Pair Bermuda shorts with a structured waist-length shirt or cropped jacket — this keeps you from looking sloppy.
Joie Merci Shorts in Steel.
$158, Joie, Greenwich, CT, joie.com
Alice + Olivia High-Waisted Lace Shorts.
$385, aliceandolivia.com
If the shoe fits…Valentine Rockstud Gladiator Mid Chunky Heel Sandal.
$995, intermixonline.com
If the shoe fits…Loeffler Randall Mara cap-toe espadrille.
$195, loefflerrandall.com
If the shoe fits…Gentle Souls Lace Up Gladiator Sandals.
$195, bloomingdales.com