“I tell you, I started off really when I was a teenager. I had a–and I still have it–a big scar on my forehead from when I ran through a glass door when I was little,” he said. “And I was always self-conscious, so when I started singing in high school it kinda bothered me. It was bigger and bolder then; I guess it’s kinda worn down over the years. I first started wearing a hat when I was about 17, my old brown cowboy hat. That’s the hat I wore to Nashville when I came.”
“Well, everybody doesn’t look good in a hat,” Jackson said. “I’ve always thought I looked better in a hat. It’s about picking what fits your face and head right–if you’ve got a wider, bigger head you need a wider brim. You don’t want a small brim if you’ve got a big head. And same way with that crown. The top of the hat, you’ve gotta be careful with that. You really have to experiment with it and pick colors that are good. Like, I never have been able to wear a black hat. I always loved it. But every time I put a black hat on it looks goofy on me because I’m so fair lookin’. Dark guys look better in a black hat.”
Nowadays, examples of stylistic choices that help define a singers’ image usually involve sunglasses (Eric Church) or baseball caps (Luke Combs), not Western wear.