Early Bruce Springsteen and the E Street Band may be among the the only rock musicians in to make the hat work for them on stage and in publicity shots. The Specials are the only other band that come to mind from the highly scientific top of my head. Am I missing someone obvious? Most of the hat-wearing rock musicans I can think of look silly: all those truck driver chic sorts from Brooklyn and other non-farming communities in high-resting John Deer caps; anyone who’s tried rocking a baseball cap on stage; rockers in cowboy hats (which work quite well on actual country musicians); the guy from Modest Mouse in his G.I. Joe cap… The beret is inherently silly looking, so Dr. John and Mink DeVille look as silly as anyone else who’s ever worn a beret.
With the hat’s rich tradition in blues, country, soul, jazz, and other building blocks of rock ‘n roll, it’s a wonder the hat hasn’t fared better in rock. For a rock musician to look good in a hat, is it necessary that the musician is playing a hat-appropriate form of rock ‘n roll, such as ska or horn-fueled R&B-based rock? Note how the E Street Band dropped the hats once they moved past their early horn-fueled era.
As a side thought, is it a coincidence that country music’s most rock-friendly musician, Johnny Cash, didn’t wear a hat?