Lizzy Caplan

Lizzy Caplan. Photo by Getty Images.

Who: Lizzy Caplan

Where: Outside “Jimmy Kimmel Live” in Los Angeles.

When: Tuesday, June 23rd

What: A gingham Lela Rose Fall 2015 dress, black sunglasses, and Birkenstock-style sandals.

Why: With a long hemline and a dark red lip, Caplan proves summer’s most controversial shoe can be chic—albeit not necessarily ideal for every social situation.