Hair Highlights: Messy Chic

Simply Put: With her fine hair, Dree Hemingway opts for a simple (but not too perfect) middle part that's balanced by an unexpectedly bright lip.

Nothing but Neck: Trendsetting star Olivia Munn opts for an easy, finger-raked bun that's ideal for showing off a neckline with flourish.

Loose and Luxe: Model Lily Donaldson pulls off elegance with ease thanks to her subtle waves. Style hint: Dry the hair around your face and let the rest dry naturally for an unfussy look that's still polished.

Natural Occurrence: Fashion plate Alexa Chung is the master of downtown cool. Here, she looks as if she air-dried her coveted shoulder-length bob and just ran out of the house.

Low & Behold: Beachy waves and loose strands add the right amount of nonchalance to a low pony on Wanderlust star Malin Akerman.

Side Dish: Even though a side ponytail is undone by design, actress Theresa Moore kicks her style up a notch by teasing the hair at her crown before cinching her locks.

Top Notch: Leave it to Nicole Richie to make a knotted bun look chic. A structured jacket adds a touch of elegance to her casual 'do.

Down Time: British fashion fixture Poppy Delevigne works the off-duty model look with hair that seems as if it styled itself.

Pretty Pony: Fresh-faced actress Jennifer Missoni scores big with a super-casual high pony.