Hollywood's Stylish Bachelors

From well-tailored Tom Cruise to hippie-chic Bo Bice, check out the most fashionable single celebs, as selected by PEOPLE fashion expert Susan Kaufman. By Serena Kappes

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BRAD PITT

"Brad Pitt is a guy who knows fashion and has always worn the best of menswear – like Prada and Dolce & Gabbana suits," says Kaufman. When he isn't dressed up, he enjoys a rough-and-tumble look with scruffy leather and beaten-up boots. "He's a bit of a rebel," says Kaufman.