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

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Source: The Associated Press; the Web site WhoWonWhen.com. "Winners" announced early in January for the previous year.