What was once reserved for the New England boarding school crowd has been made cool again thanks to nouveau prepsters like Alexa Chung, Olivia Palermo, Gwyneth Paltrow, and Jenna Lyons, who revamped preppy mecca, J. Crew. I’m a huge fan of the style because it’s classic and sporty, slightly tomboyish and the new spin on it gives it a downtown edge that’s cool yet effortless.

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