Style History: Diddy
Diddy recently turned 42 and is still so influential in the game. Take a look back at his stylish moments throughout the years.
Image via Complex Original
LEAD
Can't nobody hold him down! Say what you want, but Diddy is unstoppable. Ever since the late Heavy D gave him his first chance in the music industry, Sean Combs has changed the hip-hop game and made himself a millionaire with multiple business ventures (and awesome rants). The success of his Bad Boy label, Sean John clothing brand, and Ciroc vodka wouldn't be the same without his eye for style.
None of our Style History subjects have lasted in the game as a relevant player as long as Diddy has. So check out the looks we've covered from his days in high school, to stunting in Versace with Biggie, to Dirty Money performances today.
high school 2
WHEN: 1980s
WHERE: High School Photo
Complex Says: Is this the club photo for the Mathletes or Future Billionaire of America? Either way, the prep swag is palpable. Is that Kid Cudi on the right?
High School
WHEN: 1980s
WHERE: High School Photo
Complex Says: Even in high school, Puff was killing 'em with that million dollar style.
Video Interview 91
WHEN: 1991
WHERE: Video Interview
Complex Says: Here's Puff in a video interview in '91 with his mentor, Andre Harrell. When's the last time you've seen him rock the baldie?
karl kani 93
WHEN: 1993
WHERE: Karl Kani Ads
Complex Says: The Karl Kani ad campaigns are so cool to look back at now. Don't miss Nas and Tupac's modeling days either.
Yo MTV Raps 94
WHEN: 1994
WHERE: Yo! MTV Raps Interview
Complex Says: Right after he founded Bad Boy, with a Naughty Gear jacket on! Young Puff was getting that money.
mig mack 94
WHEN: July 1994
WHERE: The B.I.G. MACK campaign, shot by Chi Modu
Complex Says: This famous photo of Biggie, Diddy, and Craig Mack shot by reknowned photographer Chi Modu was for a Bad Boy feature in Billboard Magazine.
95 mtv awards
WHEN: 1995
WHERE: MTV Awards
Complex Says: Diddy's been doing this shit, Drizzy.
1995 billboards
WHEN: December 1995
WHERE: Billboard Music Awards
Complex Says: This image is iconic, when these three were on top.
97 soul train
WHEN: March 1997
WHERE: Soul Train Awards Show
Complex Says: Diddy in an all white get-up? Classic. And how can we forget Biggie's velvet moments.
97 Billboard
WHEN: May 1997
WHERE: Billboard Music Awards
Complex Says: All-camo-everything. Swag.
Shiny Suits
WHEN: 1997
WHERE: "Mo Money Mo Problems" Music Video
Complex Says: Puffy and Bad Boy singlehandedly made late '90s hip-hop about luxury and designer gear. Also, Shiny suits will never die.
97 video awards
WHEN: September 1997
WHERE: MTV Video Music Awards
Complex Says: Repping for his best friend, R.I.P.
Rush Hour Premiere 1998
WHEN: September 1998
WHERE: Rush Hour Premiere
Complex Says: We don't know what's more awkward, the leather outfit or Magic Johnson's bear hug from behind.
Kids Choice Awards 1998
WHEN: April 1998
WHERE: Kids Choice Awards
Complex Says: The fit of these jeans must be called Ross.
1998 mtv music awards
WHEN: September 1998
WHERE: MTV Music Awards
Complex Says: This look is a mix of old Harlem and Union Square bum, but he still pulled off the hat and coat in his own way.
vh1 fashion awards 1998
WHEN: October 1998
WHERE: VH1 Fashion Awards
Complex Says: A pimp from the '70s couldn't even try to look better than this. The white on white with fur is so fresh.
Source Awards 1999
WHEN: 1999
WHERE: Source Awards
Complex Says: Here, Diddy reps the West and East.
1999
WHEN: 1999
WHERE: Unknown
Complex Says: We're kind of loving this boater hat look on Diddy. Judge us all you want, but this is swag.
VMA's
WHEN: September 2000
WHERE: MTV Video Music Awards
Complex Says: What would a timeline of Diddy's stylish moments be without J.Lo?
2000 bloomingdales
WHEN: September 2000
WHERE: Bloomingdales in New York City
Complex Says: You can't mention Diddy and Sean John without thoughts of the classic velour suit.
2001 billboard music awards
WHEN: May 2001
WHERE: Billboard Music Awards
Complex Says: Varisty: Nice. The size: A bit OD.
Oct 2003 Marathon
WHEN: October 2003
WHERE: New York Marathon
Complex Says: Remember when Diddy sported a mohawk and ran the marathon? Memorable moment for sure.
2003 mtv vma's
WHEN: 2003
WHERE: MTV Video Music Awards
Complex Says: Yes, bucket hats were cool once upon a time.
2004
WHEN: 2004
WHERE: Unknown
Complex Says: Possible halloween costume for next year.
Cadillac Records
WHEN: November 2008
WHERE: Cadillac Records Premiere
Complex Says: The fur trim is oddly appropriate for the Premiere of the musical biopic.
2008 mtv awards
WHEN: September 2008
WHERE: MTV Video Music Awards
Complex Says: This makes us want a Sean John suit, stat.
2009 fifi event
WHEN: 2009
WHERE: FIFI Event
Complex Says: We're starting to appreciate the Sean John look.
white party 09
WHEN: July 2009
WHERE: Diddy's Annual White Party
Complex Says: We couldn't leave out a White Party outfit. We heard that 2009's party in Beverly Hills was the best yet.
Supreme
WHEN: 2009
WHERE: Supreme photoshoot with Terry Richardson
Complex Says: Streetwear!
2010 Glasglow
WHEN: September 2010
WHERE: Glasgow, Scotland
Complex Says: No comment.
2010 mtv movie awards
WHEN: May 2010
WHERE: MTV Movie Awards
Complex Says: The denim jacket with leather sleeves gets our co-sign.
Jalouse
WHEN: Unknown
WHERE: Outside Jalouse
Complex Says: Now this beefed up varsity jacket is something we'd like to see dude in more. And by dude, we mean ourselves.
Hangover II
WHEN: May 2011
WHERE: The Hangover, Part II
Complex Says: Another win on the sartorial side for Diddy.
Jul 1, 2011
WHEN: July 2011
WHERE: Club 55
Complex Says: Diddy in his chilled out look, versus his many outrageous 'fits.
2011
WHEN: September 2011
WHERE: Studio
Complex Says: Givenchy is taking over hip-hop.
