Gary LeVox, born Gerald Wayne Vernon, Jr., burst onto the country music scene as the big-voiced lead singer of 1999's breakout band Rascal Flatts. Despite his natural talents for hitting all the impossibly high notes, his talent for choosing designer duds was sometimes questionable, like in this "Then" picture from the 2002 ACM Awards, leaving his young, eager style much to be desired.

Two children, 12 No. 1 singles and more than 20 million albums sold later, LeVox seems to have transitioned into fatherhood and super-stardom with grace. He, along with bandmates Joe Don Rooney and Jay DeMarcus, are often credited as staples of red carpet fashions, and the stylish musicians even joined forces with J.C. Penney in 2009 for their own fashion line.