The first thing Tim and Diana agreed on? The beard had to go. "I have to say Miles was very open to this—nervous, a little trepidatious—but very open," Tim says. "When she started to take away the hair on the face, we began to see this incredibly handsome, powerful guy emerge."
Diana says any man can actually pull off facial hair if he's willing to commit to grooming it. "When it comes to the beard, what's most important is that you don't let it go," Diana says. "You have to maintain it on a daily basis. You have to trim away the stray hairs. You have to mold it into a shape. It's kind of like having the right haircut."
Miles loves his new look—clean face and all. "I'm feeling great," he says. "I hadn't seen my lip in like 30 years."
Jacket: beige leather, HugoBoss.com; shirt: Roundtree & Yorke short sleeve, Dillards.com; shirt: Roundtree & Yorke merlot button down, Dillards.com; T-shirt: Tommy John, Nordstrom.com; denim: Levi's 501, Dillards.com; belt: Ralph Lauren Polo, Dillards.com; boots: Too Boot, Dillards.com.