"People made a big deal out of Chris Young ditching his cowboy hat," says Veronica Alfaro, radio personality on WQYK-FM 99.5, a country music station in Tampa Bay. "But it worked.

Chris Christmas, a fourth-generation Black cowboy with Native American roots, considers the cowboy hat to be an indispensable part of his heritage. “I think I was born with a cowboy hat,” said ...