Make Over My Man!
Inspired by Undateable, a wickedly funny new guide to the style mistakes men make, O takes on six self-sabotaging guys—nominated by the women who love them—and shows them six ways to improve their look.
Before and after shots of Robb Tennant
Robb Tennant, 29, with girlfriend Jacqueline Nicholls

Before: Too much facial hair is one of Undateable's main deal breakers. But for Robb, a musician with the alternative-folk band Rooftops, not shaving was a symbol of mourning based on Jewish ritual: His mother died five years ago, and he found it tough to move on. Robb's teenage clothes also needed to evolve. "I'd like him to look more clean-cut and sophisticated," says girlfriend Jacqueline, a fashion designer.

After: "From Amish farmer to Robert Redford!" raves Anne Coyle, coauthor of Undateable. The suit is slightly rumpled, so he looks hip, not stiff, and his shoes are worn sockless. Contacted a month after his transformation, Robb reports a "92 percent positive response" to his absent beard (just like a guy to quantify): "I expected teasing and jabbing, but people are surprisingly supportive."

Suit, J.Crew, $366. Shoes, Florsheim by Duckie Brown. Shirt, Brooks Brothers, $80. Tie, Ralph Lauren Purple Label, $135. On Jacqueline: Dress, Kate Spade New York, $395. Earrings, Helen Ficalora. Bracelets, House of Lavande, CC Skye. Shoes, Stuart Weitzman.