Before They Were Fashionistas
Jessica Simpson 12/5/00
2000 was not a good year in fashion for Jessica Simpson, who had yet to hire Annabel Tollman as her stylist. At that year's Billboard Music Awards, Jess stepped out in a seriously short little black dress and knee-high black boots. A lot of skin, yes, but still cute. What sent this look over the edge were the feathers-cum-floaties adorning her arms. While she didn't fly away, her name flew onto a number of worst-dressed lists.