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30 Awkward Style Moments in Hip-Hop

Hip-hop style has come a long way from b-boys in tracksuits breakdancing in the streets to rappers like A$AP Rocky gracing the pages of high-fashion magazines, Pharrell designing for Adidas, Nicki Minaj creating a line for Kmart and Kanye West sitting front row at Paris Fashion Week.

While the art form has evolved and the culture has grown, our ability to count on hip-hop for bewildering style choices throughout the years stays exactly the same. Some of our favorite MCs have fallen into the “what not to wear” category more than once.

Lucky for us, T-Pain‘s hats, Lauryn Hill‘s hobo-chic misadventures, Drake‘s endearing hipster interpretations and Missy Elliott‘s love affair with all that is shiny only scratch the surface of awkward style moments.

Memorable fails from Snoop Dogg, Ghostface Killah, Da Brat, Grandmaster Flash, Fabolous, Ice-T, Diddy and Foxy Brown, among others, prove good music isn’t enough to steer clear of the fashion police. Check out 30 Awkward Style Moments in Hip-Hop.

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