Where: 2005 Emmy Awards
Carrie set a high fashion standard from quite early on. She went for that dark and mysterious look at 2005's Emmys with this floor-length, black-and-sequined halter gown, paired with a broody smoky eye, of course.
Where: 2006 Country Music Awards
She won Song of the Year for "Before He Cheats," but looking at Carrie in her nude, mermaid-inspired gown with that sexy, plunged neckline, it's hard to imagine anyone cheating on this classic beauty.