The Worst Hip-Hop Fashion Fails of All Time

From controversial to bizarre outfits.

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Complex Original

Image via Complex Original

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Style is an indelible facet of hip-hop. It's how rappers differentiate themselves. Skills are important, yes, but no MC, no matter how deft on the mic, is worth a second listen unless he or she has a unique and compelling sense of style. Vocal inflection, cadence, flow, creativity with wordplay—these are aspects of style we get from the songs. But equally as important to any hip-hop legacy is style as it relates to fashion.  

Good or bad, iconic moments in fashion are often more memorable than the music. Hip-hop history's heavyweights are as known for their contributions to style as they are for their songs—Slick Rick and his abundant gold chains, LL Cool J's Kangol, Flavor Flav's clock, Run DMC's adidas, Ma$e's shiny suits. Yes, their musical contributions are significant, but when you play the word association game with their names, it's often their signature fashions that come to mind first.

We thank the trendsetters for their hit moments in hip-hop style over the years. And then there are the misses—or the fails, as we affectionately refer to them. Mistakes, lapses in judgement, bad decisions, "what the fuck were you thinking?" moments—they happen to all of us. But when you're in the spotlight, performing at a live event, in a music video, or on the cover of your album, these lapses become unforgivable historical documents. And nothing is more fun than collecting them all in one place for your LOLtastic pleasure. From Lil Wayne's women's jeggings to the Choppa Suit, click through and enjoy The Worst Hip-Hop Fashion Fails of All Time.

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50. Jay-Z's chancletas

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49. The Furious Five's costume party

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48. Q-Tip's rhinestone jeans

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47. Lil' Wayne's moon boots

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46. MC Serch's high-top fade

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45. Foxy Brown's leather body wrap

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44. Flavor Flav's pajama party

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43. Three 6 Mafia's gothic S&M swag

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42. Common's sleeveless crochet hooded sweater

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41. Dr. Dre's World Class Wreckin' Cru uniform

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40. Diddy's kilt

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39. Cam'ron's streetworker chic

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38. LL Cool J's bedazzled sweatshirt

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37. Kool Keith's pink Speedo

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36. 50 Cent's sleeveless dress shirt

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35. Coolio's bald braids

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34. Jay-Z's green suit

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33. Nas's pink suit

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32. Soulja Boy's massive hoodie

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31. Kurtis Blow's sequined blazer

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30. Mystikal's hair extensions

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29. Lauryn Hill's clown costume

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28. Kriss Kross's backwards pants

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27. Cee-Lo Green's Patti LaBelle drag

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26. Kwamé's polka-dot tragedy

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25. Hammer's animal skin Speedo

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24. Kanye West's taco meat buffet

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23. Snoop Dogg's French manicure

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22. Kool Moe Dee's wild wild mess

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21. Canibus's silver body paint

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20. Lupe Fiasco's equestrian struggle

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19. Pras's shiny flamenco suit

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Where: The Refugee Camp All-Stars' "Avenues" music video

When: 1997

After all the sequined jackets we just saw, Pras shows up in a white flamenco suit for his dance battle. It's unclear at what point this outfit made sense. A white flamenco suit with white sunglasses? Really? Truthfully, though, Pras' style in this video was an all-around fail. 

18. Lil Mama's baby gear

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17. Big Daddy Kane's purple paisley shirt and arm cast

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16. 50 Cent's G-Unit camisole

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15. Prince Be's lace face mask

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14. Busta Rhymes's sleeveless Vietnamese tunic

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13. Sugarhill Gang's redface invasion

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12. Nicki Minaj's stuffed animal outfit

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11. Lord Infamous's nose toothpick

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10. Lil Flip's leprechaun costume

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9. Lil B's grandma earrings

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8. Ludacris's Confederate suit

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7. Choppa's Choppa suit

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6. Nas and Kelis's "N*gger" shirts

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5. Lil' Kim's face cage

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4. Vanilla Ice's "Word To Your Mother" suit

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3. Lil' Wayne's animal print jeggings

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2. will.i.am's blackface Gumby

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1. MC Hammer's harem pants

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