Sarah, Duchess of York - Feb. 9, 1990
Sarah Ferguson, who married Prince Andrew, Duke of York in 1986, rocks an oversized sweater and fetching boots at a skiing competition while pregnant with her second child, Princess Eugenie. Marital bliss didn't last long for Fergie, who allegedly had extra-marital affairs and was divorced from Andrew after 10 years of marriage. Though she retained her Duchess title, Fergie became a royal outcast, culminating in a tawdry episode in which she attempted to drunkenly sell access to her ex-husband, Prince Andrew, and was caught doing so on tape by a reporter for the now-defunct News of the World. Fergie didn't make the 1,900-person guest list to the royal wedding of Prince William and Kate Middleton, but her daughters, Princess Beatrice and Princess Eugenie, stole the show with their outlandish fascinators.