I'm on a Dwight Yoakam kick for some reason.
This is a good collection of his stuff:
So, he looks pretty slick and hip, right? Always has the beat up hat with the serious curvature. Wears tight jeans, usually kind of beat up. He's always cultivated a bit of a rebel/rocker outsider image.
Here are some of his album covers...
And then, a couple years ago I was shocked when I saw him in a movie, sans hat
...and realized why he wears it. =)