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Bring at least one fun evening dress and one or two casual night out ensembles to cover all your bases here

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Credit: Scott Wintrow/Getty Images September 2007 The singer paired her bubblegum pink dress with bright accessories and a feather fascinator at a Fashion Rocks party in New York City

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Sinclair, 26, on a recent warm afternoon sauntering through Domino Park in Williamsburg, Brooklyn, slick forelock curled in an anime flip, inked arms emerging from the sleeves of a sinuous Issey Miyake pleated dress