Kenny Chesney – Then and Now

Much like his music, Kenny Chesney's style has evolved over time. In 2000, he turned up at the CMA Awards wearing this light gray, three-button suit. We're afraid to look at old photos to see if everyone was wearing their jackets to the knees earlier this century, but we'll give him the benefit of the doubt and assume that was the case.

Nowadays, the country singer is usually much more relaxed during television appearances or at award shows. He'll put on his stiff, black hat for more formal events, but if he can get away with a t-shirt and jeans, he'll do it. Chesney is noticeably more toned now than he was 12 years ago. The lines of time show on his face, but certainly not in a bad way. Most fans of this superstar's fans will agree that he continues to look better as the years pass by.