Serena van der Woodsen of Gossip Girl (played by Blair Lively) opted for the road less traveled. Judging from her her power-prowess outfit — Herve Leger bandage skirt, Slane & Slane layered necklace, and gray Topshop blazer — I deduce she’s heading to a fashionable business meeting of sorts. Her take on business casual is far from boring and leans on the sexy side — true to Serena van der Woodsen nature. And who can miss her decadent embellished Valentino tote? How fly is this outfit? — Ramlah Boadi

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