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The Coolest Girl In Town

Let me introduce you to a new idea: Making your most powerful outfit not look powerful at all. As if you got dressed without thinking too hard, almost like an accident.  Carolyn Bessette has mastered this illusion. A white button down, a black skirt, a slip dress, and undone side parted hair. Nothing about it felt loud, yet the images of her running away from paps in New York city have become some of the most referenced pictures till date. Her outfits never tried to impress vogue’s critiques, but that's exactly why they were.  Let me be honest with you, the illusion of looking unbothered is never an accident, it’s careful consistency. Build your wardrobe around a narrow set of choices: sharp outerwear, personal stacks (I am done seeing Rolex watches, a tennis bracelet and a Cartier), almost undone lipstick, completely undone hair, and a lot of Calvin Klein dresses. And it’s okay to repeat silhouettes constantly, repetition creates clarity. But also the role of mystery is very ...

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