I am obsessed with the "Caroline" maxi dress from Milly. Obsessed! Chevron stripes are one of my favorite preppy patterns and are just perfect for a poolside soiree at the club. The unexpected color combination of Hermes orange and nautical navy will make your tan pop and the rattan espadrille and clutch keep this look summertime specific. Hot trend this season? Match your lipstick to your outfit and you'll be in with the ladies-who-lunch crowd before you can perfect your backhand.