Following her Oscar win, Gwyneth became a fashion darling -- and the face of Dior's City Dior handbag. It would be the first of many fashion and beauty deals for the stunning actress, who would grow to have an illustrious reign at the top of many a best-dressed list. In 2005, she became the face of Estée Lauder's Pleasures fragrances, scoring a $1-million-a-year paycheck for the partnership. She then became a brand ambassador for Coach during their 2011 and 2012 seasons. Reed Krakoff, Coach's executive creative director, called Gwyneth "a natural choice." Finally, in 2012, Gwyneth joined Hugo Boss, hawking their Boss Black Boss Nuit Pour Femme perfume, and inked a deal to become the face of cosmetics brand Max Factor.