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    Photo Gallery

    Mr. Blackwell's Worst Dressed: The Past 20 Years

    By Richard Lawson, 11:52 AM on Mon Oct 20 2008, 20,527 views (Edit post, Set to draft, Slurp)

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    Sad news that catty style assessor Mr. Blackwell passed away this weekend. Though, maybe not so sad for the decades' worth of celebrities that he slammed as his Worst Dressed picks of the year. If you're curious about who Mr. B selected as his top (bottom?) choice each year since 1960, you can find a list here. We've also compiled a photo gallery of the most recent 20, after the jump.

    • 
Sarah "Fergie" Ferguson, 1988
    • Sarah "Fergie" Ferguson, 1988
    • 
LaToya Jackson, 1989
    • LaToya Jackson, 1989
    • 
Sinead O'Connor, 1990
    • Sinead O'Connor, 1990
    • 
<a class="autolink" title="Click here to read more posts tagged JULIA ROBERTS" title="Click here to read more posts tagged JULIA ROBERTS" href="http://gawker.com/tag/julia-roberts/">Julia Roberts</a>, 1991. Image via Getty
    • Julia Roberts, 1991. Image via Getty
    • 
Madonna, 1992. Image via Getty
    • Madonna, 1992. Image via Getty
    • 
Glenn Close, 1993 (Photo not from that year, obvs.)
    • Glenn Close, 1993 (Photo not from that year, obvs.)
    • 
Camilla Parker Bowles, 1994
    • Camilla Parker Bowles, 1994
    • 
<a class="autolink" title="Click here to read more posts tagged HOWARD STERN" title="Click here to read more posts tagged HOWARD STERN" href="http://gawker.com/tag/howard-stern/">Howard Stern</a>, 1995
    • Howard Stern, 1995
    • 
<a class="autolink" title="Click here to read more posts tagged DENNIS RODMAN" title="Click here to read more posts tagged DENNIS RODMAN" href="http://gawker.com/tag/dennis-rodman/">Dennis Rodman</a>, 1996
    • Dennis Rodman, 1996
    • 
<a class="autolink" title="Click here to read more posts tagged SPICE GIRLS" title="Click here to read more posts tagged SPICE GIRLS" href="http://gawker.com/tag/spice-girls/">Spice Girls</a>, 1997
    • Spice Girls, 1997
    • 
<a class="autolink" title="Click here to read more posts tagged LINDA TRIPP" title="Click here to read more posts tagged LINDA TRIPP" href="http://gawker.com/tag/linda-tripp/">Linda Tripp</a>, 1998
    • Linda Tripp, 1998
    • 
Cher, 1999 (Image via Getty)
    • Cher, 1999 (Image via Getty)
    • 
<a class="autolink" title="Click here to read more posts tagged BRITNEY SPEARS" title="Click here to read more posts tagged BRITNEY SPEARS" href="http://gawker.com/tag/britney-spears/">Britney Spears</a>, 2000
    • Britney Spears, 2000
    • 
'Weakest Link' host <a class="autolink" title="Click here to read more posts tagged ANNE ROBINSON" title="Click here to read more posts tagged ANNE ROBINSON" href="http://gawker.com/tag/anne-robinson/">Anne Robinson</a>, 2001
    • 'Weakest Link' host Anne Robinson, 2001
    • 
<a class="autolink" title="Click here to read more posts tagged ANNA NICOLE SMITH" title="Click here to read more posts tagged ANNA NICOLE SMITH" href="http://gawker.com/tag/anna-nicole-smith/">Anna Nicole Smith</a>, 2002
    • Anna Nicole Smith, 2002
    • 
<a class="autolink" title="Click here to read more posts tagged PARIS HILTON" title="Click here to read more posts tagged PARIS HILTON" href="http://gawker.com/tag/paris-hilton/">Paris Hilton</a>, 2003
    • Paris Hilton, 2003
    • 
<a class="autolink" title="Click here to read more posts tagged NICOLETTE SHERIDAN" title="Click here to read more posts tagged NICOLETTE SHERIDAN" href="http://gawker.com/tag/nicolette-sheridan/">Nicolette Sheridan</a>, 2004
    • Nicolette Sheridan, 2004
    • 
Britney Spears, 2005
    • Britney Spears, 2005
    • 
Paris/Britney tie, 2006
    • Paris/Britney tie, 2006
    • 
Victoria "Posh Spice" Beckham, 2007
    • Victoria "Posh Spice" Beckham, 2007

    Read More: Photo Gallery, Fashion, Mr. Blackwell, Cher, Anna Nicole Smith, Britney Spears, Paris Hilton, Nicolette Sheridan, Victoria Beckham, Linda Tripp, anne robinson, Dennis Rodman, Howard Stern, Spice Girls, Julia Roberts, Madonna, Top, Jezebel

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New York, 3:43 PM
Mon Jul 6
28 posts in the last 24 hours

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