There’s been men in country music you’d rarely see without their trademark cowboy hat dating back to Hollywood’s singing cowboys in the ’30s and ’40s and honky tonk heroes from the ’50s like Hank Williams.
By the ’90s, country singers were either hat acts like Alan Jackson, or, in the cases of Marty Stuart and Travis Tritt, their image was partially built on never wearing hats on stage.
When considering Jackson’s look, it’s easy to assume that like most of his songs, his Stetson hat reflects an appreciation for country music legends. Yet per a 2018 interview with GQ, it turns out that the future ’90s heartthrob started wearing a hat while in public because he was self-conscious about his appearance.
