Leighton Meester might not be a privileged Manhattanite a la her Gossip Girl character Blair Waldorf, but she’s doing pretty darn well for herself despite being born to a convict. (She’s even joked with the press, “Look, I could’ve turned out a lot worse,” when questioned about her upbringing.) In addition to prowling the Upper East Side while filming her hit series, Leighton signed a recording contract with Universal Republic in 2009 and sang a Rascal Flatts song for the soundtrack of her flick Country Strong. She’s the current face behind Herbal Essences and Vera Wang just selected Leighton as the face of her newest fragrance, which will be released in the spring of 2011. Her natural beauty and talent are definitely taking her farther and farther career-wise, and these full rectangular Yves Saint Laurent sunglasses are definitely Gossip-worthy with this outfit!

Buy these now: Yves Saint Laurent 6254/S, $174