Mr. Blackwell's worst-dressed list, year by year.
1960: Anna Magnani
1961: Debbie Reynolds
1962: Zsa Zsa Gabor
1963: Zsa Zsa Gabor
1964: Barbra Streisand
1965: Princess Margaret
1966: Mia Farrow
1967: Barbra Streisand
1968: Julie Andrews
1969: Queen Elizabeth
1970: Sophia Loren
1971: Ali MacGraw
1972: Raquel Welch
1973: Bette Midler
1974: Helen Reddy
1975: Caroline Kennedy
1976: Louise Lasser
1977: Farrah Fawcett
1978: Dolly Parton
1979: Bo Derek
1980: Brooke Shields
1981: Barbara Mandrell
1982: Diana Spencer (Princess Diana)
1983: Joan Collins
1984: Cher
1985: Princess Stephanie of Monaco
1986: Meryl Streep
1987: Lisa Bonet
1988: Sarah Ferguson
1989: LaToya Jackson
1990: Sinead O'Connor
1991: Julia Roberts
1992: Madonna
1993: Glenn Close
1994: Camilla Parker Bowles
1995: Howard Stern
1996: Dennis Rodman
1997: Spice Girls
1998: Linda Tripp (Clinton scandal figure)
1999: Cher
2000: Britney Spears
2001: Anne Robinson ("Weakest Link" host)
2002: Anna Nicole Smith
2003: Paris Hilton
2004: Nicollette Sheridan
2005: Britney Spears
2006: Paris Hilton, Britney Spears (tie)
2007: Victoria "Posh Spice" Beckham