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performing at a live event, in a music video, or on the cover of your album, these lapses become unforgivable historical documents.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
49. The Furious Five's costume party
48. Q-Tip's rhinestone jeans
47. Lil' Wayne's moon boots
46. MC Serch's high-top fade
45. Foxy Brown's leather body wrap
44. Flavor Flav's pajama party
43. Three 6 Mafia's gothic S&M swag
42. Common's sleeveless crochet hooded sweater
41. Dr. Dre's World Class Wreckin' Cru uniform
40. Diddy's kilt
39. Cam'ron's streetworker chic
38. LL Cool J's bedazzled sweatshirt
37. Kool Keith's pink Speedo
36. 50 Cent's sleeveless dress shirt
35. Coolio's bald braids
34. Jay-Z's green suit
33. Nas's pink suit
32. Soulja Boy's massive hoodie
31. Kurtis Blow's sequined blazer
30. Mystikal's hair extensions
29. Lauryn Hill's clown costume
28. Kriss Kross's backwards pants
27. Cee-Lo Green's Patti LaBelle drag
26. Kwamé's polka-dot tragedy
25. Hammer's animal skin Speedo
24. Kanye West's taco meat buffet
23. Snoop Dogg's French manicure
22. Kool Moe Dee's wild wild mess
21. Canibus's silver body paint
20. Lupe Fiasco's equestrian struggle
19. Pras's shiny flamenco suit
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.