Jessica Szohr may have no shot in this one. Leighton Meester's a strong competitor, and, well ... she's channeling Gothic Barbie a little too much for our taste.
You be the judge, though. As you can see, she donned oversized shorts and a drapey silk cardigan and platforms at a fashionable Maybelline New York event.
Her Gossip Girl co-star, meanwhile, opted for the high fashion route in a color block Giambattista Valli dress with a draped front at NYC's Cipriani Wall Street.