The latest episode of Gossip Girl was filled with oodles of pretty plaid, but one in particular caught my attention. While most of the Upper East Siders took the preppy route, Serena van der Woodsen's structured Smythe Les Vestes jacket and buckle boots add a polished equestrian aura to her stylish school-girl vibe. A white button-up top, gray tights, and shark tooth necklace complete her outstanding outfit — an A+ in my book!

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Photo courtesy of the CW