Photo: Jonathon Kambouris

21 of 25
Old School: You can't wear boots in summer.

New Rule: Behold the summer bootie! Choose a pair in a lighter color and with a lower shaft height, and feel free to wear them with shorts, skirts or dresses. Bonus: Pick a closed-toe version and you can skip the pedicure.
Rag & Bone, $525;