From PEOPLE Magazine Click to enlarge
He's a billionaire, so how come he doesn't look like at least a million bucks? The 51-year-old real estate conquistador lives in his Manhattan Trump Tower amid the world's toniest shops, but the elegance hasn't traveled up to his penthouse. Even two fashion-conscious ex-wives failed to shore up the master builder. Rumpled, shaggy and a shade behind the times, Trump, our judges rule, needs some wardrobe reconstruction. "He doesn't really have a style," says designer Deena Appel. "But he definitely has the means and motivation to be more modern." TV host Barbara Smith advises, "Get a personal shopper." And all agree that Trump could use a breath of fresh hair. Says MTV's Kennedy: "He needs to stop trying to fool everyone with the comb-over."

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