Gossip Girl, 2009  THE ROLE: Leighton Meester as Blair Waldorf  SONG: "Prom Theme" by Fountains of Wayne  WHY WE LOVE IT: In a scandalous battle from prom queen, Blair triumphed over her rivals in a gorgeous Marchesa gown—completing a fairytale night (minus breaking up with Nate).

The Most Iconic Prom Dresses of All Time

Blair Waldorf and Penelope Shafai at their school Constance Billard........

The Ex-files - Blair Waldorf (Marc by Marc Jacobs cape, Alexandra Vidal top, Marc by Marc Jacobs shorts + Jennifer Behr headband).

Oscar de la Renta. Perfection.

Tips on how to dress like Blair Waldorf

Blair Waldorf in Oscar de la Renta An unexpected but brilliant color combo. Red Oscar de la Renta gown and fuchsia accessories: Roger Vivier clutch, Christina Loubouton heels, and Harry Winston fine jewelry.