Leighton looks as fresh faced as ever, somehow managing to make a pair of metallic skinny jeans look effortless. Her breezy silk blouse and oversized necklace look are just enough to set her apart without going over the top.

Leighton stays classy in her revealing minidress, accessorizing with simple diamond stud earrings and a matching clutch, while metallic heels add an extra something special.

Always a fan of designer Julie Haus, Leighton Meester shows her support at her fashion show wearing a sweet pink confection of a dress accented with statement-y black and white sandals.

Leighton shows her love for jewel tones in this stunning deep magenta number. She keeps the neckline clean, instead adding a couple baubles at her fingers and ears. Criss-cross strap heels add just enough edge for this New York City girl.

Leighton Meester smiles through another day of filming Gossil Girp, taking on the humid New York summer in an easy printed maxi dress that she dresses down effectively with basic Havaianas. A two tone See by Chloe bag gives the bohemian casual look a modern touch.

Leighton goes green for the Teen Choice Awards, donning a draped Grecian dress appropriate for the screen goddess she is. She threw on a belt to carve out that tiny waist and a pair of ever-reliable peep toe platforms.

Leighton is a girl that gets the classic appeal of a simple black dress, but she makes sure to give it a current touch with fiercely strappy gladiator sandals and an outsized ring.

Leighton shows us there’s no need to be intimidated by the idea of wearing a maxi dress casually. Flat sandals, oversized sunglasses, and a hobo bag make for a look that is earthy but still sexy.