1. 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.

2. Joie Merci Shorts in Steel.

$158, Joie, Greenwich, CT, joie.com

3. Alice + Olivia High-Waisted Lace Shorts.

$385, aliceandolivia.com

4. If the shoe fits…Valentine Rockstud Gladiator Mid Chunky Heel Sandal.

$995, intermixonline.com

5. If the shoe fits…Loeffler Randall Mara cap-toe espadrille.

$195, loefflerrandall.com

6. If the shoe fits…Gentle Souls Lace Up Gladiator Sandals.

$195, bloomingdales.com