Mark Chesnutt
We knew they looked good in cowboy hats, but would two of country's young hunks flip for other lids? Chesnutt was leery: "Most of 'em, I thought, 'No way am I gonna put that on my head.' " Yet he proved to be a natural cutup in every hat he tried on. The Texan, 31, whose third album, ALMOST GOODBYE, just went platinum, does own dozens of cowboy hats and 300 to 400 caps—some of them decades old. Will any of the hats here make the grade? "Not anytime soon."

Neal McCoy
"I love hats," says McCoy, whose third album, No DOUBT ABOUT IT, has gone gold. While some of our choices had him howling ("Very stupid," he muttered at one), the affable Texas native does know his way around a Resistol. "You wear felt in the winter, straw in the summer," he notes. "And I try to match the color to my boots or belt. It's kinda tacky if you don't." With 12 cowboy hats and plenty more gimme caps, McCoy, 36, seldom has hair bare. "A hat's like a security blanket," he says.