Country music star Travis Tritt has shared countless stories from his legendary career, but one memory involving Waylon Jennings still makes him laugh decades later.
In a recent interview, Tritt reflected on the early 1990s, when he was carving his path in Nashville with his signature “no hat” look—a rarity in a country music world dominated by Stetsons and cowboy boots. “I had all this hair back then,” Tritt joked. “I thought, why in the world would I cover it up?”
Waylon Jennings, known for his humor and straight talk, gave Tritt a piece of advice that stuck. The two had collaborated on “Old Outlaws Like Us,” and as the song faded out in the studio, Jennings could be heard teasing, “Travis, you may be the best—but I think you need a hat.”
Tritt said the playful jab was classic Waylon. “He was basically telling me, ‘Son, this is country music—you better at least look the part!’” The moment became one of Tritt’s favorite anecdotes from his early career, capturing the camaraderie and humor of country music’s outlaw legends.
Today, Travis Tritt still occasionally dons a cowboy hat, but he’s grateful he followed his instincts back then. His decision to stand out—along with timeless hits like “Here’s a Quarter (Call Someone Who Cares)” and “The Whiskey Ain’t Workin’” with Marty Stuart—cemented his place among country music’s most enduring artists.