Before picking up her razor, Diana says she asks her male clients about their personalities—and Eric is no exception. "Eric wakes up and just wants to go," she says. "He doesn't want to fit one particular personality but be more the fun, cool guy." Now, Eric's looks falls somewhere between banker and bearded caveman.

Will Eric keep his new look this time around? "I think so," Eric says. "Absolutely!"

Eric's look: Joe's Jeans "Bixton" Straight and Narrow Jeans, available at Bloomingdale's; Theory "Reynold Style" Shirt in rich navy shirt, available at Bloomingdale's; Dark Brown Goat Suede Jacket by John Vartos Star USA, available at Barneys New York.

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