Blackwell's Worst Dressed
Mr Richard Blackwell is a fashion critic who every year releases his ten worst dressed list. The list started in 1960.
Britney Spears now leads in this dubious distinction having been singled out three times. Paris Hilton, Cher, Barbra Streisand, and Zsa Zsa Gabor have each 'won' twice.
| Year | Worst Dressed | Runner Up |
| 2008 | Victoria Beckham | Amy Winehouse |
| 2007 | Britney Spears | Camilla Parker-Bowles |
| 2007 | Paris Hilton | Camilla Parker-Bowles |
| 2006 | Britney Spears | Mary-Kate Olsen |
| 2005 | Nicollette Sheridan | Lindsay Lohan |
| 2004 | Paris Hilton | Madonna; Britney Spears |
| 2003 | Anna Nicole Smith | Kelly Osbourne |
| 2002 | Anne Robinson | Britney Spears |
| 2001 | Britney Spears | Angelina Jolie |
| 2000 | Cher | Celine Dion |
| 1999 | Linda Tripp | |
| 1998 | Spice Girls | |
| 1997 | Dennis Rodman | |
| 1996 | Howard Stern | |
| 1995 | Camilla Parker-Bowles | |
| 1994 | Glenn Close | |
| 1993 | Madonna | |
| 1992 | Julia Roberts | |
| 1991 | Sinead O'Connor | |
| 1990 | LaToya Jackson | |
| 1989 | Sarah Ferguson | |
| 1988 | Lisa Bonet | |
| 1987 | Meryl Streep | |
| 1986 | Stephanie Grimaldi | |
| 1985 | Cher | |
| 1984 | Joan Collins | |
| 1983 | Diana Spencer | |
| 1982 | Barbara Mandrell | |
| 1981 | Brooke Shields | |
| 1980 | Bo Derek | |
| 1979 | Dolly Parton | |
| 1978 | Farrah Fawcett | |
| 1977 | Louise Lasser | |
| 1976 | Caroline Kennedy Schlossberg | |
| 1975 | Helen Reddy | |
| 1974 | Bette Midler | |
| 1973 | Raquel Welch | Julie Andrews |
| 1972 | Ali MacGraw | Jacqueline Kennedy Onassis |
| 1971 | Sophia Loren | Angie Dickinson |
| 1970 | Queen Elizabeth | |
| 1969 | Julie Andrews | Carol Burnett |
| 1968 | Barbra Streisand | Julie Christie |
| 1967 | Mia Farrow | Julie Andrews |
| 1966 | Princess Margaret | Barbra Streisand |
| 1965 | Barbra Streisand | Jayne Mansfield |
| 1964 | Zsa Zsa Gabor | Elizabeth Taylor |
| 1963 | Zsa Zsa Gabor | Rosalind Russell |
| 1962 | Debbie Reynolds | Sophia Loren |
| 1961 | Anna Magnani | Brigitte Bardot |
Email Dan@WhoWonWhen.com with suggestions for new lists, or to report spelling or other errors.
Every attempt is made to insure the accuracy of the above information, however accuracy is not guaranteed.
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