“It’s pretty self explanatory,” says Kendra. Just pull on the beanie, tilt it back on your head, pull the top part back and down, and tuck in your hair. “I was always trying to wear a more tailored hat but it looked kind of uptight. The slouchie look has a much more relaxed vibe, and I think it gives you more street cred!”

How pretty does Kendra look?

Thanks, Kendra!

P.S. Kendra’s navy nails.

(Photos by Alpha Smoot for A Cup of Jo. Styling by Kendra Smoot. If you’re wondering, Kendra’s beanie is from Madewell (now sold out), her snood is from French Connection, her jacket is from Madewell, her bag is vintage Coach and her boots are Sam Edelman)