The Worst Hip-Hop Fashion Fails of All Time

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performing at a live event, in a music video, or on the cover of your album, these lapses become unforgivable historical documents.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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Where: France

When: 2005

Going on vacation may mean a chance to take a break, but even on your days off chancletas are no-nos. Frankly, no one's exempt from this rule, not even Jay-Z. What did Cam'ron say again? "How's the king of New York rocking sandals with jeans? Open-toe sandals with chancletas with jeans on?"

Where: Ebet Roberts promotional photo shoot

When: 1980

The Furious Five, along with Grandmaster Flash, is one of the best-dressed crews in hip-hop history. Which is why the photo and outfits above are that much more disappointing. It's no secret that their style eventually grew to be flashy and reflected the rock and disco elements in their music, but this makes no sense at all. The caption in the image probably describes it the best: "Grandmaster Flash and the Furious Five would live to regret firing their stylist."

Where: Vibe magazine cover

When: March 2000

Q-Tip's eccentric sense of style went way left with he donned these infamous rhinestone jeans.

Where: "The Motto" music video

When: 2011

Lil Wayne continued his absurd style choices in "The Motto" video rocking a pair of neon green Forfex moon boots. Yes, moon boots. Meanwhile, Drake wore a rare Supreme jacket and Tyga rocked vintage Versace alongside the YMCMB boss. SMH.

Where: Everywhere

When: 1989-1990

You might be baffled as to how MC Serch was able to grow a high-top fade, but don't forget he could also execute a flawless running man. Anyway, his hair has been compared to Kim Jong-Un's ’do, and that's actually not a compliment to either of them.

Where: B.B. Kings in New York City

When: 2010

During her performance, Foxy Brown told the crowd, "This is what we tell all the haters: You can't keep a good bitch down." True, but you can also keep a good bitch indoors, especially if she's wearing this. The face of the guy in the back says it all.

Where: MTV Video Music Awards

When: 1990

Flavor Flav has rocked pretty wild outfits over the years, even showing up to the "Los Premios MTV Latin America 2008" Awards dressed as a bullfighter. But this ensemble trumps all: Flav attended the 1990 VMAs in straight Kanye West "Sorry I'm in pajamas, but I just got off the PJ" style—except he (probably) didn't fly private, and looked a lot less luxurious than Yeezy's lyrics sounded.

Where: MTV Movie Awards

When: 2007

Around this time, Three 6 Mafia launched their new clothing line of men's and women's apparel under the moniker, Dangerus and Skandulus. The garments were rock-inspired and featured skull designs, which could explain the gothic theme they had at the MTV Movie Awards. Still, they took the promotion a little too far, especially with the spiked accessories.

Where: The "Geto Heaven" music video

When: 2001

Common was the resident king of the tree hugger bohemian look. He owned it, whether it was kufis or crocheted sweaters he was rocking. Usually, we'd give him props for his unique sense of style, but this sleeveless crochet hooded sweater is a no-no. Even just typing that out sounded horrible.

Where: Everywhere

When: Mid-’80s

Before N.W.A, it was the World Class Wreckin' Cru, and Dr. Dre wore shiny red suits, not Raiders snapbacks and Cuban link chains. This was a dark era for Dre's style.

Where: Scotland

When: 2010

Puffy headlined MTV Crashes Glasgow wearing traditional garb: a kilt. We understand he may have wanted to show love to his Scottish audience, but he doesn't quite pull it off as Kanye West, A$AP Rocky, and Theophilus London all have in more recent times. Why? For starters, he's bearing his legs—put some pants underneath! Also, the jacket and the, not one but two, cross chains.

Where: The "Confessions Of Fire" cover

When: 1998

Cam'ron has started a few trends over the years, including wearing pink. But this greased-up Cam in denim overalls is a fail. Too much skin, Killa Cam.

Where: MTV Video Music Awards

When: 2006

Early in his career, LL Cool J seemed to be ahead of the pack, starting a few trends we've come to love. But at some point, he may have been overwhelmed by all the fads that came and went, and was unsure of what to rock and what to pass on. Take for instance the bedazzled hoodie he wore to the 2006 MTV VMAs. Maybe he was trying to outshine (literally) 50 Cent, who he arrived with. Either way, the ladies did not love Cool J, or Todd Smith, that night.

Where: The Sex Style album cover

When: 1996

Pink Kangol, pink speedo, black cowboy boots. Not Kool, Keith.

Where: GQ magazine cover

When: 2005

It's a bird, it's a plane...it's a Super Fail!

Where: Everywhere

When: 2010-present

To say Coolio is married to his braids is almost an understatement. The rapper had braids when he first hit the scene, though of course he actually had a head full of hair then. He's practically bald now but he's still holding onto his struggle braids. He just needs to let go and find a new look. Maybe he can take the advice Shaquille O'Neal gave LeBron James: Come home; bald is beautiful.

Where: "Sunshine" music video

When: 1997

This video birthed the Jay-Z and Joe Camel comparisons, as well as this shiny green suit. Hov's suit and tie game was a little off in the clip because his outfit reminds us of either a leprechaun or Bishop Don "Magic" Juan's pimp suit. Either way, not a good look. Good thing Hov has come a long, long way from this.

Where: "Street Dreams (Remix)" music video

When: 1996

We get it. Real men wear pink, right? Well this pink suit is just supa ugly. Right, Jay-Z?

Where: "Crank Dat (Superman Dat Hoe)" music video

When: 2007

Soulja Boy's "Crank Dat" may have been one of the most popular songs at the time, but we can't overlook the XXXL hoodie he wore in the video. If you ask us, he's to blame for making guys think it's okay to wear large hoodies—large airbrushed hoodies, mind you.

Where: Krush Groove / The "If I Ruled The World" music video

When: 1985

Kurtis Blow started off with a simple white shirt and black pants in the first few second of the "If I Ruled The World" video. But when his backup dancers brought out his sequined blazer, it was game over. Is it just us or does he looks like the Penguin in Batman, as played by Michael Jackson?

Where: Everywhere

When: 1993-1999

Now you know why the man right chea sounded so damn angry all the time.

Where: Concert at Brooklyn's Wingate Field

When: 2007

Every now and again, Lauryn Hill puts on a show and performs old material from The Miseducation of Lauryn Hill and the Fugee's The Score. In 2007, she hit the stage in Brooklyn and shocked fans with different renditions of her classics. That and she came out in a clown costume—if you google "Lauryn Hill clown costume" the photo above pops up. Why is she caked? And she is way over dressed for the heat with all that leather?

Where: The Totally Krossed Out era

When: 1992

The late Chris Kelly of Kris Kross once said that he never stopped putting his pants on backwards. "Even if I put on a suit, I put my suit pants on backwards," he told Hip Hop Media Training. "It's just a way of life for me." Years later and the group's trademark look still confuses us. How the hell do you pee?

Where: BET Awards

When: 2011

We know Cee-Lo is never one to miss an opportunity to surprise the audience with his stage outfits. But was it really necessary to dress up as Patti LaBelle during his tribute to the soul singer? Not to mention, bring a can of hairspray on stage and spray his wig? SMH.

Where: The "U Gotz 2 Get Down!" music video

When: 1989

"Your life is played out like Kwame and those f**kin' polka dots," rapped Biggie. All that needs to be said.

Where: "Pumps & A Bump" video

When: 1993

Why the hell is MC Hammer wearing a zebra-print Speedo? With gloves? And humping these poor women? MTV couldn't figure it out either, which is why it banned this video for being "too graphic."

Where: GRAMMY Awards

When: 2006

The 2006 GRAMMY Awards would have been a near perfect night for Kanye (he collected three awards, including Best Rap Album) if only he hadn't worn this white blazer-and-taco meat outfit. Even Yeezy himself has expressed some regret over the ensemble, telling us in our August 2007 issue that "even Jordan had off days."

Where: Instagram

When: 2013

Today in things that don't make sense: Snoop with a French manicure. After all these years of smoking, it looks like the weed may finally have gotten to the rapper's head. We just want the old Dickies-and-Chucks Snoop back. That's not too much to ask, right?

Where: "Wild Wild West" video

When: 1988

The song is called "Wild Wild West," so at some point, in made sense to dress up Kool Moe Dee in a full cowboy outfit. Just. Not. This. One. Kool Moe Dee is a legend, but this all-leather-everything look with no shirt and white cowboy boots is a legendary fail.

Where: MTV Video Music Awards

When: 1998

Style-wise, there was a lot happening at the 1998 MTV VMAs. Marilyn Manson rocked a green and blue leopard print suit. His then-girlfriend Rose McGowan wore a dress (can you even call it a dress?) that left nothing to the imagination. Lil' Kim sported a purple jumpsuit with only a sticker to cover her left breast. Busta Rhymes and the Flipmode Squad were dressed as a mariachi band. Still, Canibus managed to stand out, though in this case it may not have been in such a great way. The rapper performed in silver body paint. When asked about the aforementioned paint, he said he wasn't trying to win an award for best-dressed. He said it was because it felt good; because he was shining. Sure.

Where: MTV Video Music Awards

When: 2008

Lupe's outfit was a fiasco, from the vest to the riding jodhpurs. And we can't forget about the OJ Simpson glove. The rapper told Miss Info that he planned on debuting his Fall of Rome line on the red carpet but was instead forced to go to plan B after the garments didn't make it through customs. Plan B was this look by a Belgian label called Les Hommes. In the words of Miss Info, "that which looks awesome in a Men’s Vogue editorial spread set in the French countryside….doesn’t always translate in real life."

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.

Where: MTV Video Music Awards

When: 2007

We get it, Lil' Mama is the voice of the young people. But she took it too far and too literal. Was it really necessary to dress up as a baby? After this the boys definitely did not "keep jokin'" and chase her after school.

Where: Heavy D's "Don't Curse" music video

When: 1991

While Heavy D & the Boyz wore striped pajamas, Kane rocked his famous purple paisley shirt with matching scarf (and a cast!). BDK told Scion (yes, the car company) that he loved that shirt until a friend of his told him it looked like a bullfighter shirt. Wise friend.

Where: Various live performances

When: 2003-2005

G-Unit is definitely one of the best-dressed crews in hip-hop history. So it only makes sense that their clothing line is easily one of the most successful celebrity brands, raking in $50 million in the first year. In its five years of existence, it brought us plenty of camo, widely popular "Property of G-Unit" T-Shirts, and even sneakers. But with all that said, we still can't get behind the camisole 50 Cent was often spotted in. It's a little reminiscent of the very, very in-shape Timbaland and his camisoles, no?

Where: PM Dawn's "Looking Through Patient Eyes" music video

When: 1993

Is Prince Be wearing Victoria's Secret on his face? Someone find dude so he can finally solve this Hardy Boy mystery.

Where: MTV Video Music Awards

When: 1997

Before Busta started working out and eventually became The Rock's body double, there was this, a time when the rapper wore kimonos. He presented the award for Best Dance Video with Martha Stewart, making for one of the biggest hip-hop moments in pop culture, but unfortunately, also wore this outfit that slightly looks like it was made out of curtains. In his own words, "What the dilly, yo?"

Where: Unknown

When: 1982

Daniel Snyder is probably the only person who didn't find this vintage Sugarhill Gang performance offensive.

Where: MTV Video Music Awards

When: 2011

You never really know what you're going to get with Nicki Minaj, especially when it comes to her outfits. The YMCMB rapper walked the red carpet at the 2011 MTV VMAs wearing what looked like a stuffed animal ensemble with flat boots. Now, anyone who's been paying attention to her knows that she rocks some of the craziest gear. We've come to accept it and even love her for her unapologetic attitude and sense of style. But she looks slightly like a strange Japanese toy here. Sorry Barbs.

Where: Three 6 Mafia's "Tongue Ring" video

When: 2000

Lord Infamous clearly embraced piercings (especially tongue rings on women, apparently). When it came to his personal style, the jewelry was a big part of his persona, and something his fans remembered. But a nose piercing? A needle through his nose, mind you. The crazy thing is, he's the reason why some guys got nose piercings...

Where: The Leprechaun album cover

When: 2000

Lil Flip (probably) heard it from everyone for wearing this leprechaun costume, inlcuding T.I., who the rapper had beef with a few years back. T.I. At the 2004 Birthday Bash concert, T.I. freestyled, rapping "What kind of n---a take a picture in a leprechaun suit with a lollypop chain and some leprechaun boots?/ ... Being lame is a curse you can never undo." Flip dug a grave for himself.

Where: "Got The Mack Loaded" music video

When: 2012

Rappers have worn earrings for years, so that's not the problem here. The problem is is Lil B rocking chandelier earrings, straight grandma style—the kind of earrings hipster girls find at the Brooklyn flea market. The video, and his questionable accessory, were met with some criticism—even A$AP Rocky had a few words to say about it—and led to tons of parodies.

Where: Vibe Awards

When: 2005

Here's another outfit that caused some controversy. Ludacris caught some flack back in 2005 for wearing this Confederate suit while perfoming "Georgie" at the Vibe Awards. Some thought it was another example of a rapper's ignorance. Still, Luda said he wore the flag to make a statement. "This flag represents the oppression that we as African Americans have endured for years; this is a symbol of segregation and the racism that reigned not only throughout the South but throughout the entire United States. I wore it to represent where we came from, to remind people that Ray Charles’ original “Georgia” was written because of that racism..."

Where: WorldStarHipHop

When: March 9, 2009

Back in 2009, Chopper City posted a video online of his rant about E. Ness from Making Da Band. He went on for 12 minutes. But let's be honest, no one paid attention to what he was saying. Everyone was too focused on his over-sized suit that must have been from 20 years ago. The Internets had a field day with this one, producing tons of parodies and memes. Even Bow Wow got a kick out of the "Choppa suit."

Where: GRAMMY Awards

When: 2008

Nas and Kelis shocked everyone at the GRAMMYS when they walked the red carpet in their matching "N*gger" shirts. When a CNN reporter asked the Queens rapper to share the reasoning behind their outfits, Nasir said the "word is supposed to be ignorant" and that it was all about "the experiences we go through every day, of all ethnicities—Black, White, indifferent." If Nas wanted to make a statement, he definitely got people's attention.

Where: The Soul Train Lady of Soul Awards

When: 1998

Before Lady Gaga, there was actually Lil' Kim, who if you paid attention, wore some pretty extreme outfits to award shows. Take for instance, this cage headpiece she wore to the Soul Train Lady of Soul Awards that slightly looks like a medieval knight's chainmail coif.

Where: Saturday Night Live performance

When: 1991

Ice took his style to self-parodic levels with this black-and-silver suit that was so shiny it looked like it was made of Reynolds Wrap. And oh yeah: The jacket had "Word to your mother" printed on the back. So there's that. Truth be told, it looked kinda dope on Jim Carrey, though.

Where: MTV Video Music Awards

When: 2011

This is possibly one of the most memorable moments in VMA history: Lil' Wayne in women's jeggings. Weezy already had people talking before it was confirmed that he was indeed wearing women's pants because said pants were so tight. But once the news hit, the Internets had a field day—someone even made a Lil Wayne Jeggings Twitter account. Years after the fact and it's still equally hilarious and terrible.

Where: MTV Video Music Awards

When: 2010

will.i.am stirred up some controversy when he performed "Check It Out" with Nicki Minaj at the VMA pre-show in his black gumby costume. Some called it racist, referring to the resemblance to blackface. Following all the backlash, will addressed the outfit, tweeting "Just because I wear all black including head mask as expression and emphasize my outfit, it shouldn't be looked at as racial." True, not everything should be considered a racist act. It's also true that some artists prefer to wear costumes on stage to further express their creativity, and because it's part of the performance. But it's hard to disagree with the fact that will's black gumby outfit is anything but a fail.

Where: "U Can't Touch This" video

When: 1990

These drop-crotch pants are still associated with Hammer, so he does get some props for wearing something and making it widely popular. But file them into the category of trends that should have never happened. If you find yourself considering these pants, ask yourself, "If Hammer jumped off a bridge, would I?" Because in reality, harem pants just make you look like a former fat guy who couldn't lose the weight in his thighs.