Aaron after

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Oversize sweaters with loud patterns may have defined Bill Cosby's style, but Tim says that was a different era. Aaron's new sweater has polish and sophistication. "It doesn't mean a patterned sweater can't work—just not that pattern," Tim says. "Go with something classic like an argyle."

Tim also updated Aaron's look by shaving his mustache and convincing him to lose his pleated pants. "It was all he was wearing," Tim says. "You look slimmer in these pants."

T-shirt: Calvin Klein, Nordstrom.com; sweater: Nordstrom.com; jacket: Faconnable, Nordstrom.com; pants: Zanella, Nordstrom.com; shoes: Dolce & Gabbana, Nordstrom.com