Then and Now

Toby Keith – Then and Now
Toby Keith – Then and Now
Toby Keith – Then and Now
Toby Keith's style has quieted down since the mid-90s photo on the left. Back then, the singer tamed a rare breed of mullet: the perm-mullet. His hair is naturally curly, but one doesn't get that sort of bounce without a little help from the ladies at the beauty salon.
Faith Hill – Then and Now
Faith Hill – Then and Now
Faith Hill – Then and Now
Faith Hill has changed her look more than a few times since debuting in this somewhat dowdy, very country velvet dress in the early '90s. By 2001, the singer straightened her hair and began to show her midriff at major award shows. Steamy videos followed, which was especially impressive since she'd just had a kid with husband Tim McGraw.
George Strait – Then and Now
George Strait – Then and Now
George Strait – Then and Now
George Strait's music isn't the only thing that doesn't age. The famous country singer looks remarkably similar today as he did when this "Then" photo was taken over 30 years ago. The King wasn't even 30-years-old when he began his country music career, yet somehow he took the stage with the confidence of performers who'd been doing it for decades.
Keith Urban – Then and Now
Keith Urban – Then and Now
Keith Urban – Then and Now
Keith Urban actually looks younger at age 44 than he does in the 'Then' shot from 10 years earlier. Perhaps it's just the light, but he seems to have less wrinkles, and his skin is a healthy pink instead of a color that matches his blonde hair.
Taylor Swift – Then and Now
Taylor Swift – Then and Now
Taylor Swift – Then and Now
When Taylor Swift walked the ACM Award red carpet in 2006, most photographers were left scratching their heads, wondering which artist brought his or her teenage daughter and why she'd gone rogue. These days, the country music superstar carries herself a little differently, but the same humble girl still shines through.
Kenny Chesney – Then and Now
Kenny Chesney – Then and Now
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.
Hank Williams Jr. – Then and Now
Hank Williams Jr. – Then and Now
Hank Williams Jr. – Then and Now
Hank Williams Jr. had a mountain climbing accident in 1975 that almost killed him. After that, he's kept the now-famous beard and sunglasses close by for public appearances, but this press photo from 1971 proves he wasn't always the surly country picker we know today. Heck, he looks borderline cheerful.
Rascal Flatts’ Joe Don Rooney – Then and Now
Rascal Flatts’ Joe Don Rooney – Then and Now
Rascal Flatts’ Joe Don Rooney – Then and Now
Rascal Flatts' guitarist Joe Don Rooney has always been on the leading edge of country fashion, so we'll cut him some slack and assume that the outfit he has on at the 2001 ACM Awards put him in a number of 'Best Dressed' lists. A decade of country hits has chiseled his then boyish face into one women scream for on a nightly basis. A model wife has no doubt helped him stay on top of his fashion ga
Brad Paisley – Then and Now
Brad Paisley – Then and Now
Brad Paisley – Then and Now
It didn't take long for Brad Paisley to begin picking up major awards at country music ceremonies. Musically, you can still hear the man he was in the late '90s or 2000 (when this "Then" picture was taken) in his songs today, but he's come a long way in the style department. His look today is a little less... traditional.
LeAnn Rimes – Then and Now
LeAnn Rimes – Then and Now
LeAnn Rimes – Then and Now
Now before you start making fun of LeAnn Rimes' "Then" photo, remember that it was the late '90s and we were all prone to wearing sage green blazers. The singer has always been on the cutting edge of country fashion, so it's safe to assume that this was the style 15 years ago. Teenagers all over America were wearing stuff like that, weren't they?

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