Dennis Rodman, Harry Benson, 1996

Dennis Rodman's Most Outrageous Looks

The cross-dresser, jet-setter, peacemaker — and one-time basketballer — has always had a flair for the fabulous.

Not So Tickled Pink, 1997 Michael O'Neill/Corbis via Getty Images Not So Tickled Pink, 1997 White Wedding, 1996 Evan Agostini/Getty Images White Wedding, 1996 Mad Hatter, 1999 Jeff Kravitz/FilmMagic, Inc Mad Hatter, 1999 Smokey Eyes, 1999 MR Photo/Corbis via Getty Images Smokey Eyes, 1999 Better Off Dead, 2005 Bennett Raglin/WireImage Better Off Dead, 2005 Graffiti Artist, 1996 Andy Hayt/NBAE/Getty Images Graffiti Artist, 1996 Ample Support, 2005 Chris Polk/FilmMagic Ample Support, 2005 Silver Lining, 2011 Jim Rogash/Getty Images Silver Lining, 2011 Limited Visibility, 1997 Bongarts/Bongarts/Getty Images Limited Visibility, 1997 Footballer, 2005 Brad Washburn/FilmMagic Footballer, 2005 Formal Attire, 2005 Jean Baptiste Lacroix/WireImage Formal Attire, 2005 Sparkly Sequins, 2013 Stephen Lovekin/Getty Images Sparkly Sequins, 2013 Furs and Pearls, 1996 Carl Sissac/The LIFE Images Collection/Getty Images Furs and Pearls, 1996 Nostril Spikes, 2006 Chris Weeks/WireImage Nostril Spikes, 2006 Rebounder, 1996 Rocky Widner/NBAE/Getty Images Rebounder, 1996