Keepin’ It Country Ain’t Only Reason Alan Jackson Wears a Hat

Alan Jackson: Mustache, jeans, dirty blonde hair, and a cowboy hat. ‘Nuff said. Ain’t nobody who’s had so much success in country music that has kept it as country as Alan Jackson, not just with his music, but with his actions, like the time he stopped down performing his own song at the 1999 CMA Awards to sing “Choices” by George Jones in protest, or told his drummer to play with no sticks when the ACMs demanded he perform to a backing track, or recorded “Murder on Music Row” with George Strait.

Part and parcel with all of that is the rarity to ever see Alan Jackson without a cowboy hat on. Sure, there are a few photos of Alan Jackson lidless, but only when he dips his hat in honor or gratitude. He’s never shown up to an affair or performance without one on. But this isn’t just an adornment to prove how country he is. There’s actually a practical reason for the ever-present Alan Jackson accessory.

As the Georgia-native first revealed in a 1992 interview with People Magazine, when he was a kid, he ran head first into a plate glass door, giving him a good horizontal scar across his mid forehead. Since then, headgear has been a requisite for Alan Jackson .

“I’ve just kinda gotten used to wearing them,” Jackson told GQ a while back. “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. 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.”

Alan Jackson was born in Newnan, Georgia, and grew up in a house built out of his grandfather’s old tool shed. Jackson’s mom lived in until she died. Jackson had been married to his high school sweetheart Denise for 6 years before deciding to move to Nashville to pursue music full time. Once they hit Music City, Jackson needed to do something to support the household, and took a job in the mailroom of The Nashville Network’s (TNN) offices. He later met Glen Campbell and the rest is history.

“Everybody doesn’t look good in a hat. I’ve always thought I looked better in a hat,” Jackson continued to GQ. “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.”

Jackson says Stetson felt hats are his headgear of choice, and he even shapes the brims and crowns himself. Even when he’s kicking it casual on a boat or in a convertible (yes, he really drives them, not just in videos), Jackson still wears a hat, though it’s usually a baseball cap.

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