Leighton Meester’s character on Gossip Girl is the ultimate definition of upscale chic. She always looks prim and polished, with her collection of blouses, pencil skirts and tweed blazers. You can count on her to put feminine touches on all of her clothes, like lace, ruffles and bows. She goes preppy at times too (able to pull off the skinny tie), and loves slipping on a silk headband or other fab hair accessory. Her mother is a fashion designer. What else could we expect?