Bonanza Alan Jackson Cowboy Hat Style Pick

Alan Jackson Cowboy Hat

Most people associate country singer Alan Jackson – the twang-y crooner behind hits like “It’s Five O’Clock Somewhere” and “Chattahoochee” – with his signature cowboy hat.

As one of the best-selling music artists of all time, Jackson’s country music style blends honky-tonk with mainstream country. And it fits perfectly with his cowboy hat style choices.

The country music singer pairs his light-colored and traditionally shaped Alan Jackson cowboy hat with a wide variety of black and brown embroidered jackets. His shirts have untucked pearl snap shirts. And he loves western-style suits and custom boots. The look is a blend of carefully put-together choices and a relaxed “I just threw this on” look. 

Alan Jackson in a traditionally styled silver belly hat
Jackson pairs a traditionally styled silver belly hat with an embroidered jacket for a visit to New York City. The bound edge completes the dressed-up look. (Brian Ach/WireImage)

Why the Alan Jackson Signature Cowboy Hat?

Jackson has discussed his hat choice several times over the years. He began wearing a cowboy hat at the age of 17 to cover a big scar on his forehead. The scar conjures images of a young rodeo cowboy riding bulls.

In fact, it was just an everyday accident. “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 has admitted in numerous interviews so this is common knowledge by now.

At the start of his career, it made him feel more comfortable in front of an audience. Over the years, the scar and his confidence faded as his popularity grew. But wearing an iconic Stetson remained a key part of his image.

Although the Alan Jackson cowboy hat has changed over the years, he has chosen very similar colors and shapes. Let’s talk about three of Jacksons’ old and new hat choices. 

Alan Jackson Cowboy Hat Style

Alan Jackson in a relaxed Taco Brim Cowboy Hat
Jackson performs at the 39th Annual CMAs wearing a silver belly with a honky-tonk spin. The relaxed taco brim with a square front is a nod to the classic country artists that inspired Jackson. (Kevin Winter/Getty Images)

You won’t see Jackson wearing a black hat—he feels that a lighter color hat matches best with his light complexion. This silver belly hat features a matching bound edge on the brim and a matching hatband. The shape is a traditional Low Cattleman crease with a George brim shape.

The reason that each of Jackson’s hats features a slightly different, yet familiar shape, is because he shapes them himself. By using steam, he’s able to shape the hat to perfectly fit his tastes. This hat features the Low Cattleman crease that Jackson prefers. In terms of crown height, he doesn’t like them too tall. He says they look goofy on him, because he’s tall. So he goes with shorter crowns. The 4-inch brim is shaped into a relaxed taco shape, one of his favorite brim shapes for his performance hats. The sides turn up, but not too much like Jimmy Dickens.

Alan Jackson with his wife in White Cowboy Hat
Jackson and his wife attend the 50th ACM awards in Texas. His white hat stays within his preferred color, but the crown and brim shaping is slightly different than his other hats. (Jason Merrit/Getty Images)

Hat and Music Styles

For high-profile events, Jackson chooses a more formal hat to pair with his suit jacket and jeans. We love this white hat by Stetson, which is at least a 50X choice. The Show crease on the crown maintains the cap height that Alan Jackson feels best compliments on his face shape. The wide brim features a unique rolled shape with a round brim front. The style is that of a country cowboy who makes the effort to dress up for special occasions. 

In 1979, Jackson married his high school sweetheart Denise moved to Nashville to pursue their music career. At the time, she was a flight attendant and met Glen Campbell one day at the airport. She boldly asked for his advice on her husband’s career, and Glen generously gave her his phone number. The very next day, Jackson called Campbell who hired him on the spot to write songs for $100 a week. The rest is history. (source:

The Alan Jackson Cowboy Hat Stops Here

Alan Jackson makes slight adjustments to the hats he wears. But he maintains his signature style by sticking with natural colors and similar crease styles. He maintains that he will always choose Stetson hats, and he takes great pride in shaping his own hats. You can recreate the country music legend’s style by tweaking the brim with a Cattleman’s crease in a variety of ways. Country music legend Alan Jackson’s simple style choices are easy to execute and look great on everyone.

And then the brim, you pick the width of that depending on how it looks best on you. I like to turn it up on the sides, but not too much like Jimmy Dickens. (Source:

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