Sean "Diddy" Combs Fashion Pictures

Diddy Does it Up

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  Is this the Diddy we have all come to know and love to hate? The year was 1997, and the event is the opening of Sean Comb's now defunct Justin's restaurant. With that baby face and ill-fitting suit, Diddy, then Daddy, looks like a kid who's been playing in his father's closet.

  Ron Galella, WireImage.com

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  A long time player in the game called "hip hop mogul," Diddy played tough guy with fellow baller Jay-Z 200. They both look a little ashy. This was before the major paper would come. Is that a wash cloth is Comb's back pocket? Lord.

  J. Vespa, WireImage.com

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  Continuing to try to keep it real, Diddy dated felow middle-class urbanite Jennifer Lopez in 2007. As she rocked her fake Latina gang member do rag, Combs strutted the red carpet like a princely thug.

  Frank Micelotta, Getty Images

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  Um. I don't know what to say here, except wrong, wrong, wrong and NEXT!!!! The year 2000 was a very bad year for the artist formerly known as Puffy's style sense. And who would make a red Christmas tree?

  Ron Galella, WireImage.com

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  Unfortunately, 2001 was also not a very good year. Puff hit the streets in the type of wide-legged baggy pants only reserved for a 'Fat Albert' character.

  Jim Spellman, WireImage.com

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  Always known as a great performer, Diddy took to the stage in 2002 to show the world that he is a devout Mets fan in head-to-toe gear. Still a little childish. Would Diddy's style ever transform?

  Kevork Djansezian

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  I blame Kim Porter. Again modeling his look after a member of the 'Fat Albert' cast, poor Puff dresses like a member of the Junkyard Band in an over-sized Kangol hat. He was at a 2001 Jean-Paul Gaultier fashion show people!!!! SHM.

  Serge Benhamou, Prestige / Getty Images

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  BAM! In 2003, Diddy made the change from fashion misfit to trendsetter. He filled out a little bit, and took to the runway of his own fashion show to take a bow in a well-cut suit. It's a little shiny, and the sleeves are short, but he looks good!

  Mark Lennihan, AP

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  Continuing on a winning streak, P. Did hits the 2003 MTV Movie Awards red carpet in a very mature linen suit, while sporting the super-dark sunglasses he will grow to love. Maybe they help block the paparazzi's glare.

  Dave Hogan, Getty Images

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  In 2003, Diddy wore casual outifts without having to pull off a "thug" costume, as in earlier years. He can be effortlessly himself. There go those shades again.

  Lester Cohen, WireImage.com