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