Kenny Chesney tells a hilarious Taylor Swift story on The Tonight Show. During Chesney's January 16 appearance on The Tonight Show Starring Jimmy Fallon — sporting his trademark cowboy hat, ...

Country superstar Kenny Chesney -- who performs Thursday, June 20, at Blossom Music Center -- almost never gets photographed without his trademark white Blue Chair Bay Palm Straw Cowboy Hat.

Sporting a gray T-shirt, blue jeans, boots and a black cowboy hat, Chesney opened his 15-song set with "Reality." "No Shoes, No Shirt, No Problems" was particularly a crowd favorite; Chesney got ...

Here's a sight you don't often see. Country superstar Kenny Chesney spent his New Year's Day surfing in Hawaii with a pal. He shared a photo, sans his trusty cowboy hat.

Kenny Chesney has been more willing to pose for photos without a cowboy hat in recent years than he was early in his career. Before, it was impossible to find the 'Feel Like a Rock Star' singer ...

Kenny Chesney seems like a fun guy to hang with. You know, the dude who always has a fresh batch of margaritas chillin' in the blender at his beach pad in the Virgin Islands, a bevy of bikini-clad ...

Kenny Chesney (right) and bass player Harmoni Kelley perform "Beer In Mexico" during the CMT Music Awards in the Municipal Auditorium in Nashville, Tenn., in this April 11, 2022 file photo.

Besides being the biggest male acts in country music, they all wear cowboy hats. For a long time, it was a prerequisite that to really succeed in the country music business, you had to have a hat. In ...

Dressed in a cowboy hat, jeans and a loose-hanging sleeveless Grace Potter & the Nocturnals T-shirt, the country superstar, who turned 47 Thursday, gave a three-hour 36-song set. A big star ...