Christina Aguilera
While singer-songwriter Christina Aguilera’s “Dirrty” era granted the fashion lookbook of the early-aughts with a number of memorable additions, her 2002 MTV Video Music Awards Outfit is by far the most…questionable. Turning a see-through scarf into a sling for her breasts and strutting her stuff in a micro-mini denim skirt, Aguilera rounded off her edgy look with striped hair and a chain belt. Paired with her overly-lined lips, this “outfit” is one fashion critics won’t soon forget.