Photo SpecialPEOPLE's Style Awards

Our style director, Susan Kaufman, reveals the stars who most deserve a fall fashion trophy. By Serena Kappes

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MOST DAPPER DUDE: USHER

"Usher is a throwback to the era of Frank Sinatra and the Rat Pack," says Kaufman. "It's that cool, laid-back school of dressing." The multiplatinum-selling Confessions singer knows how to work a suit – and look utterly "pulled together," from his pinky ring to his pocket square.

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