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Fashion in Hip-Hop has come a long way since its beginnings in the early 1980’s. Back then b-boys could get fly for relatively cheap–throw on a pair of Lee jeans, some shell toes with a nylon shirt and you were good money. While some of those golden era brands like Kangol and Bally would go on to become fashion staples, the Furious Five spandex swag should never be allowed to come back.

But surprisingly enough there are still many current day rappers are making sartorial choices that might be just as bad. Whether it’s due to their own poor taste or the result of a struggle stylist dressing them, some of your favorite rappers are looking bad out here.

You’ll find some of today’s most popular Rap artists in their most suspect fashion moments in the following pages. Let us know your favorite fashion fail in the comments.

Photos: BET, YouTube, XXL

We are all for revisiting that feel of the 90’s era, but Drake took things a little too far with his infamous leather Dada outfit that he donned for the “No New Friends” video earlier this year. This iconic pose would inspire much slander and still leaves us wondering what were the socks all about?

As much as A$AP Rocky professes this to be a long shirt, this will forever be the day he wore a dress and construction Timberlands to 106th & Park.

While Kanye West is given much props for helping getting us past that dreaded throwback jersey and oversized white t-shirt era, the leather skirt / kilt wasn’t the wave for us b.

Jay Z once boasted “can’t wear skinny jeans cause my knots don’t fit” but was caught in an awkward combination of skinnies and Timberlands. #Irony

Lil Wayne is a repeat offender when it comes to questionable fashion choices. From his passion for foul colored UGG boots to those infamous leopard print jeggings, Tunechi needs a fashion intervention.

French Montana looked downright silly in this bear hoodie – don’t let him fool you.

2 Chainz continues to slide down a slippery slope of wack sauce. The Atlanta rapper’s preference for luxury Italian fashion house Versace has gotten him into some interesting styling. Let’s us not forget the leather tassel moment with skirt or when he showed up to The Grammys as The Count.

It’s hard enough for our culture to be respected in corporate america when rappers are walking around with their pants sagging off their ass while speaking struggle English. Nicki Minaj sported a pink chicken necklace and let the whole world know that “Chicken Rules Everything Around Me”.

Trinidad James is wearing a denim mini skirt, mini skirt b. That is all.

Skateboard P went all types of wrong with his interpretation of black tie tuxedo with an oversized bow tie, a very young blazer, shorts and no socks.

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