Wedge flip flops outfit y2k

Britney Spears was photographed constantly in the late '90s and early '00s. Here, see photos of the pop star's best street style outfits.

You called it months ago: Jessica Simpson has officially joined Weight Watchers. While her pregnant body definitely warranted its own timeline, let's not forget that her figure has very-much been a point of discussion among gossip rags for over a decade. (Also, it's always fun to revisit those clothes and that hair.)