Jason after

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With Hollywood men's grooming expert Diana Schmidtke's help, Tim takes Jason from "farmer in the dell" to Kenny Chesney.

Before changing Jason's look, Tim says he used the Socratic Method to find out what Jason envisioned for himself. "[I had] a Q&A with Jason about how he sees himself and who his own style mentors are," he says. "We got to Tim McGraw and the country western aspects and using a classically tailored jacket with a nod to western wear with the western yoke and, of course, a pair of jeans that fit and a great cowboy boot that he loves." Tim also swapped Jason's ratty straw hat with a sleek cowboy hat.

Jason says he feels fantastic. "You wouldn't believe the looks I always got," he says.

"For all the wrong reasons," Tim says.

Boots: Alcalas.com; hat: Alcalas.com; jacket: Alcalas.com; belt buckle: Alcalas.com; T-shirt: Calvin Klein, Nordstrom.com; collared shirt: Dolce & Gabbana, Nordstrom.com; belt: Remo Tulliani, Nordstrom.com