The mid-2000s was not the best time for fashion, even for celebs who had a battalion of stylists and soothsayers to tell them what would elicit a "that's hot" and what would just be considered "ew." This was a time when the red carpet was full of clashing patterns. Ruffles and newsboy caps were completely inescapable. Actors were showing up to galas in distressed denim and faded band tees cut and slashed into bra tops. It was a dark time for anyone wondering who wore it best (No one. No one wore it best.)
With a decade separating us from the fashion mistakes of 2006, there's enough distance to view them as an anthropologist might. These celebrities have already moved into a much a brighter fashion world, not bothered by their bootcut past.
Click through to remember the truly cringe-worthy couture moments of red carpets past.