Back before Britney was feeding herself a steady diet of tranqs, fraps, husbands, court cases, and fame-whoring paparazzi, she attended five consecutive VMAs in outfits that would make absolutely nobody's mother proud (with the exception of maybe Mom of the Year Linda Hogan), constructed of fine fabrics featuring nary a thread of natural fibers, each tied (barely) together by the same common bond; from 2000's "You-Tarzan-Me-Asymmetrical" black mini-dress to 2002's Village She-People get up to 2003's Frederick's of Ho-llywood bridal collection, every outfit suggested an unfortunate encounter with a car door, pinking shears, and/or a paper shredder.
That said, all of the aforementioned cropped, tattered, and torn fashion offenses can be forgiven for her 2001 VMA performance of "I'm a Slave 4 U," when she graced the stage wearing the ultimate fashion accessory -- a live, seven-foot albino python. (Paging PETA!)
+ Check out more red carpet photos of celebs who got a little older, stopped doing their own shopping, and smartly hired stylists. Case in point, Gwen Stefani, who stopped dressing like a club-kid Smurf at a yoga retreat and is now the prettiest blond beauty in all the land (sorry Britney -- but there's still hope!)