The 50 Greatest Fashion Moments in Rap Video History

Image via Complex Original

Year: 1990

You know you've made a cultural impact when your name is still associated with a style of clothing two decades later. MC Hammer coined the term Hammer pants after he came out legs swinging and arms swaying in the video for his 1990 hit, "U Can't Touch This." He made the dropcrotch legitimately hot for a second, too. No one likes to admit that, though.

Year: 2001

This was that Bounty the quicker picker upper swag. Jada said it himself: "Got the bandana made of a napkin." Much of hip-hop fashion is about excess, but sometimes the best moments are an homage to modest roots. This is certainly one of them.

Year: 2004

White tees were anti-style, anti-consumerist, dope boy signatures—a way to flaunt disregard for fashion and individuality. From Dickies suits to the A$AP Mob's high-end designer styles, rap fashion has always been a tug of war between individual expression and rocking a uniform. The white tee was the ultimate example of the uniform, and will forever be remembered as a statement of counter-cultural street unity. Or what it looks like to wear a big white shirt.

Year: 2012

$1,500. Leather. En Noir sweats. It's a moment that future generation's will look back on with wonder and amazement. Rap, as of late, has become some sort of leather daddy S&M fetish club and this moment has so much to do with it. It's the best way to say, "I don't give a fuck," and even when you do, these pants say, "My fucks are more expensive than yours."

Year: 2001

One day, Nelly was playing basketball and got a cut on his face. He put a band-aid over it. For someone like Nelly-who has to do photo shoots and music video shoots, band-aid or not-it ended up being a noticeable blip when he rocked it in the video for "#1." Realizing that it was a source of interest, Nelly not only kept wearing it but made it his trademark look and said it was dedicated to his boy City Spud who was locked up.

Year: 1997

Hip-hop fashion is all about charting new territory, even if it means wearing your hat in the most uncomfortable manner imaginable. Why didn't anyone tell dude how awkward this looked? Or that it'd possibly result in some mean forehead acne? Fuck it, everyone jocked this style for a few months anyway.

Year: 2003

A man on a mission with a message, Nas set out to both inspire kids and make a statement when he wore a T-shirt that read 'I Am the American Dream.' Always one to go the extra step in making sure he's both seen and heard, Nas' shirt accomplished his goal of showing America that you can achieve "the dream" in more ways than one.

RELATED: 50 Things You Didn't Know About Nas

Year: 2001

Burberry's been around since 1856, but before rappers were debuting fashion lines in Paris, no one in hip-hop really knew what it was. Gucci and Louis Vuitton were the monograms du jour for the longest, then Ja Rule put the masses onto the elusive tartan pattern from England. Yeah, Styles P had the Burberry bucket hat in "We Gon Make It" a few months earlier, but "Always On Time" was a No. 1 pop song that caused way more hip-hop heads to take notice of the brand. The famous plaid has been on full blast since.

Year: 2001

For starters, there's the general audacity of a then-obese Fat Joe wearing a light blue fur coat. Like, how many animals were slaughtered for that piece of outerwear? His decision to jump into a swimming pool-with the coat on-toop this fashion choice over the top, making it an instant classic.

Year: 1998

"You done switched from Nikes to Reeboks, ha?" Reebok really should have picked up on this. The icy white souljas in Juvie's "Ha" video were the cleanest—everything else was covered in a layer of grime, from Juvenile's gold teeth to the 'Nolia projects. But those white sneakers stayed crisp.

Year: 1992

You know your fashion sense has made a definitive statement when people begin to associate you with it. Case in point: After Everlast sported the Celtics jersey in the video for "Jump Around," people thought he was from Boston (He was actually born in New York but moved to L.A.). In truth, Everlast donned the Bird jersey as a homage to Larry Legend and possibly as a nod to his Irish heritage. Smart move too, in the subsequent years House of Pain were able to brand themselves as Irish hooligans and tour with a variety of alt-rock groups. In the long run, those connections in the rock world might have helped Everlast when he picked up a guitar and went solo.

Year: 2005

The real question about this logo is, how many parents bought their kids the T-shirt with the angry snowman without realizing what it actually signified? The same ones who took their seven-year-olds to see Bad Santa, no doubt. In the mid-'00s, the snowman logo was so big that schools were trying to ban it. But fear not: Jeezy fought back, even releasing a tape called Can't Ban the Snowman.

RELATED: The 25 Best Songs About Selling Drugs

Year: 2000

Yeah, Ashton Kutcher re-popularized trucker hats, Justin Timberlake tried to take credit for re-popularizing trucker hats, and we'd freak out if we saw Judah Friedlander on 30 Rock without one, but really, the first person to make them look cool in the new millennium was Pharrell in the video for "Shake Your Ass." Of course, back then hip-hop fans were stuck in their "I'm a thug thus I wear fitteds" phase, and the look didn't really take off in the rap world, but we'll never forget that P was the true pioneer.

Year: 2008

Thanks to the War on Terror, the last decade put more brown people on American TV than ever before. Ever the iconoclast, Kanye must have looked past all politics and thought, "Damn, that scarf is kinda fresh." He started sporting keffiyehs in 2007 and the style hit its peak in the video for "Homecoming" the following year. Next thing you know, every fashion forward kid on the block started walking around trying to look like Yassir Arafat. Once the masses caught on, we're surprised that Yeezy didn't one-up everyone and rock the cloak like the best dressed world leader, Hamid Karzi.

Year: 2000

Hip-hop has a storied history with what are supposed to be undergarments. Artists are notorious for exposed boxers above sagging pants, and, wifebeaters-formally known as A-shirts. Hov wasn't the first to wear one in public, but he was the first to wear one in a rap video, on a yacht, with models, and Cristal. Suddenly casual was the new luxe.

Year: 1995

People really idolize Biggie's Versace speedboat era, and rightfully so, but you have to realize that Frank White was always a young god. This dude walked up in Nell's at 22 rocking a turtleneck under a leaher, probably fresh off depositing some of that new rap money. The ocassion was the video for "Big Poppa" and Big's whole steez in the song was completely believable because he was in there looking like the flyest dude out.

Year: 2003

Back in the day, there was only three ways to wear your hat. Straight, because you kept it a hundred and people could depend on you (think Ice Cube in the Raiders hat). Backwards, because you kept it funky fresh, but weren't to be trusted (like Wakko in the Animaniacs). Or you rocked your hat to the side because you were such a fucking rebel you refused to conform to society's agreed upon ways to wear a hat. But T.I. blew the lid off the whole fitted top game when he discovered a way to point his hat exactly at 8:55. And he angled it upward so didn't sit, it was perched on his dome ready to fly away at any moment like a sparrow. Of course, it never fell off T.I.'s head, he's too cool for the wind to blow his hat away. Sadly, the same wasn't true for the rest of us.

Year: 2004

Marginalized by their label, Clipse sat on the shelf as their their eventual classic Hell Hath No Fury languished. In the downtime, they hit the mixtape scene and caused a stir with the We Got It 4 Cheap series. Not only was Pusha's We Got It 4 Cheap shirt became such an important moment for the group. Not only did it become a popular shirt-one usually sold in mom and pops stores and not say Macy's-it was a big look for the Clipse brand. It also gave us something to look out for whenever we hit rap concerts but left our weed in our other jacket: The guy in the We Got It 4 Cheap! shirt.

Year: 2001

This was so practical when you think about it. Can't decide if your body temperature is airing on the side of hot and oppressive or cool and exposed? Ja Rule was happy to present us with a happy medium. It became a go-to move for many in summer 2001, and J. Lo made Juicy Couture the most popping women's line out in the same breath.

Year: 1997

Up until this point, you'd never seen anything like it in your life. What the hell was Missy wearing? Is that some sort of shiny garbage bag? Whatever the hell it was, it put her in a class of her own as an artist willing to take risks and do insane shit no one else would dare.

Year: 1992

These days, artist merchandise is much more widely available than it once was. However, back in the day, one of the most innovative things Naughty By Nature did was embrace merch and see its potential for revenue. After the video for "Uptown Anthem," Naughty Gear was in high demand, so much so that the crew later opened their own store called to sell it. They still sell the merch on their website to this day. When you see acts like Odd Future and Watch The Throne setting up pop-up shops, know that Naughty helped pave the way.

Year: 2002

The average rap fan probably wasn't watching too much Sex and the City in 2002, but Beyonce was. After Carrie Bradshaw made Manolo Blahnik shoes famous with the socialite set, she introduced them to hip-hop, with the help of Jay-Z. Fakes popped up everywhere and a frenzy akin to the Louboutin craze of today was initiated.

Year: 2006

Okay, maybe Pharrell and Clipse were up on A Bathing Ape before Weezy F. Baby, but you can't front like he didn't make it a little bit hotter. The brand went from something fashion conscious cool guys knew about to an aspirational, mainstream item. Wayne wore it on the cover of VIBE, too. Of course, Clipse ended up catching feelings about it and criticized Wayne for copying their style. We asked Wayne about it later and he had this to say, "Who the fuck is Pharrell? Do you really respect him? That nigga wore BAPEs and y'all thought he was weird. I wore it and y'all thought it was hot. C'mon man."

Year: 1999

Back when being a total weirdo was a relatively frowned upon, 3 Stacks unapologetically let the world know that he absolutely was one with his wardrobe choices in "Rosa Parks." Most notable, however, was the set of football pads worn as outerwear. Yeah, the baseball catcher vest was wild, but when we think of Outkast being, well, outcasts, it's this visual that comes to mind.

Year: 1993

Hip-hop is all rugged and everything, so it only made sense for this crew of youngsters to come out rocking workwear like they had a carpenter apprenticeship on the side. The intent of the style connected thought, and Carhartt became a viable, and affordable, choice many a hip-hop head who wanted to stay dipped in the latest threads.

Year: 1992

Moms was still buying normal-fitting clothes when turning 'fits backwards became a trend, it was hard for most of us to make the jeans cooperate. But you know we tried, as did every kid in America-and adults took notice. The trend was absurd, but that was the purpose. The look ultimately helped Kris Kross blow up and go multi-platinum.

Year: 1998

When Raekwon thugged his way on the screen wearing the Snoopy Iceberg sweater in the "John Blaze" video, there wasn't a kid in the 'hood or suburbs that didn't start saving lunch money and allowance to cop it. A staple in any wardrobe, the sweater, and other Iceberg designs, became a mainstay in the hip-hop world.

Year: 1993

Seattle thinks it has a claim to flannel shirts, but the early '90s saw a flannel resurgence in Los Angeles, too. Basically everything Snoop rocked, from Chucks to khakis, became a signature style, and suddenly little G's from across the country were dressed like homeboys from the barrios of L.A.

Year: 2007

Kanye West was shopping for wardrobe for his $1.2 million "Stronger" video, when he made this last-minute purchase that would cement his pop culture influence for the rest of time. The glasses, sometimes called "Venetian Blinders," aren't particularly functional, but they were massively popular, copied, and re-produced cheaply worldwide. The glasses were so pervasive that people still use their likeness as representative of 'Ye, and he hasn't worn those things in years.

Year: 2003

Have you ever seen anything this patriotic? At the time, Juelz Santana was catching heat for praising 9/11 terrorist Mohamed Atta in his raps, but he countered in the most brilliant way possible. It's all like some sort of fever dream. Is this what the term "American gangster" is about? What a searing image.

Year: 1995

Before the term swag became overused and exhausted, LL Cool J was a dude who personified it. One of the finest examples of this was when he started rocking one pant leg up in the '90s. The trend hit the hip-hop world with force and soon other rappers, fans, and everyday people were walking around sporting the look.

Year: 1997

Shiny suits made appearances in more than a few late '90s Bad Boy videos, but everyone knows that this was THE moment. While Puffy & Co. had previously adhered to an unspoken "one suit per video" rule, but "Mo' Money" found them making outfit switches every other camera cut. Blue, red, yellow-they were going all out. Couple that with what was the most visible moment for the emerging ski goggles trend, and you have one unforgettable moment.

Year: 2001

At the turn of the millennium, hip-hop headgear was certifiably out of control. In this video alone, there are fitteds, visors, du-rags, headbands, and whatever the fuck type of towel contraption Jay-Z is wearing. (Is that a T-shirt? People were wearing T-shirts on their head around then.) Headbands in paricular went hand-in-hand with the sporty look of the era, and lest we forget, only a square wears his headband the correct way. The logo should be upside down, located anywhere but front and center, and preferably over your ears or barely hanging on. It seems like dudes were really just uncomfortable with showing their full head of hair for a minute there. A nation of impressionable youth followed suit.

Year: 1995

Before the days of endless product placement in rap videos-when Ciroc wasn't around and rappers weren't pretending like Nuvo doesn't taste like stripper sweat-Mobb Deep was sipping on that Henny Rock while kicking it in the projects. And they did more than just talk about Henny (along with E&J and Bacardi 151) on their songs, they customized jerseys with the word Hennessy splashed on them. When the HNIC himself Prodigy became the world's most dangerous blogger in 2008 and made a list of trends he started, one of them included, "CUSTOM MADE FOOTBALL JERSEYS WIT HENNESSY and E&J ON EM." Word.

Year: 2004

Preppy was a uniform; it was also not hip-hop. Kanye played with both of those rules. Preppy became a way to show his individuality, with him rocking the flashiest clothes possible while still wearing collared shirts. It wasn't a way to blend in, it was a way to stand out. Hip-hop's fashion possibilities were broadened in turn.

Year: 1994

Before 3 Stacks hooked up with Erykah Badu or started wearing football equipment, he was just a kid from Atlanta. As evidenced by his indignant acceptance speech for Best New Artist at the 1995 Source Awards, he must have felt Atlanta was getting shunned by the Yankees up north and was determined to put on for his city. Thus the Braves jersey isn't just the moment of Andre's fashion sense being down to Earth (as opposed to being down to Mars), but a significant moment of hometown pride.

Year: 2004

"See these Ice Creams?" Pharrell asked on "Drop It Like It's Hot." Yeah, we see them, P. Early in this career, Skateboard P was seen as a bit of a weirdo in rap's thugged-out landscape. But as the years passed, the hits piled, and the culture shifted to a more eccentric style. Thus, Pharrell pivoted from outlier to trendsetter. Since then, he's helped open the door for adventurous closets in hip-hop and those Ice Creams were the first of many, "Damn, where'd he get those?" moments for P. Same goes for the BBC shirt. We all just wanted to be as cool as Pharrell.

Year: 1989

Flavor Flav's top hat and oversized clock necklaces are a staple in the early dawn of hip-hop fashion. Flav wasn't drapped in gold or shining in platinum, he's always had fans gawking at that big ass clock swinging from around his neck. Anyone even remotely familiar with pop culture took notice, and the look still makes for one of the greatest (and easiest) Halloween costumes in existence.

Year: 1992

The West Coast loved the black and white monochrome colors. Like Raiders hats, the White Sox cap was badass with no color to brighten up the mood and none of the glittery showmanship of the World Class Wrecking Cru. This was pure, grim gangster signification.

Year: 2002

This is one of those things we thought would never happen, but somehow did. Ask an adolescent boy what he thinks of the color pink, and he'll hit you with the stinkface and say, "Ew, pink is a girl color." Ask one of the most thugged-out rappers of the Aughts (one who popularized the phrase "no homo") and he'll tell you it's his favorite color. Cam infamously sported pink in the "Hey Ma" video and subsequently went all-pink-everything on occasion. The style managed to catch on, with high school kids walking into school rocking 6XL pink tees like it was all good. Cam later switched his color to purple for his album Purple Haze, but it wasn't nearly as popular nor infamous. The man had a pink a pink Range Rover. Come on.

Year: 2001

There was nothing cooler than walking into a high school classroom in the Aughts donning a crispy throwback. Alex English? Elgin Baylor? Pistol Pete Maravich? Sometimes we didn't even know who the players were, all we knew was that their jerseys were worth a fuckload of money. And you know who had money to spend on them? Fabolous. He was the undisputed throwback king. He rocked them in several videos, but it's his debut, "Can't Deny It," that brought his jersey-copping talents to the forefront. Why couldn't he just give us one?

RELATED: 100 Photos of Rappers in Sports Jerseys

Year: 1995

This look is so iconic that if anyone ties their bandana like this for the rest of time, they'll be compared to 2Pac. He'd been rocking the style for a bit, in public, and in the video for "So Many Tears," but its appearance in the video for No. 1 hit "California Love" was the coming out party.

Year: 1987

The Beastie Boys aren't just important figures in hip-hop for their music, but also their look. They may have been dismissed back in the days for embracing the frat and punk aesthetics, but they had a style all their own. Mike D's Volkswagen medallion wasn't prominently displayed in the video (like so many rapper chains), nor it was all that expensive, but it certainly left an impression. We can't help but see Rick Ross and the MMG crew sporting iced-out Maybach logos and think it was Mike D who set the trend.

Year: 1987

Forget snapbacks, bucket hats, and fitteds. In the '80s, cool cats were wearing Kangols and making them the most relevant accessory in hip-hop. LL Cool J has more or less had a Kangol attached to his head since he released the visual for "I'm Bad." It's a simple piece of headwear that's also representative of an entire rap generation.

Year: 2003

Jay-Z really got you dudes fooled. Knowing damn well that every fad eventually dies, he opted to "change clothes" and ditch the sports jerseys that he helped overrun hip-hop and put on a fresh new button-up dress shirt. In some ways, the throwback was already on its way out, but if you say, "Jay-Z killed the jersey," you're not reaching, either.

Year: 1994

This was definitely the era where team affiliation accounted for approximately zero percent of the reason you might rock a given jersey. Kids all wanted the Charlotte Hornest starter jackets, Miami's orange and green looked pretty fly, and Snoop definitely put Pennsylvania's black-and-yellow-black-and-yellow on the map more than a decade before Wiz Khalifa. Combine that with the afro and the gold chain...Snoop had style, and it changed the game.

Year: 1987

The God MC Rakim brought drug dealer chic to the video shoot for "I Ain't No Joke." Nobody was smiling but we're sure they were admiring. His tracksuit and gold ropes were flamboyant, something both classic and priceless. They were items that you were tempted to touch, but always seemed elusive. The allure of the items holds to this day, where artists like Drake still take advantage of the effortless cool that comes with a tracksuit and gold jewelry.

Year: 1996

Versace has experienced a massive resurgence in hip-hop lately-but long before 2 Chainz was wearing Medusa insignia to the Grammys, there was this. Despite the dozens of ways rap has repped for the brand, no image persists more than this one. Biggie was living out his larger than life, mafioso raps right in front of our eyes.

Year: 1994

Where the hell is Snow Beach? We have no idea, but when Polo released a pullover with the words Snow Beach written on it and Raekwon came through in the "Can It All Be So Simple?" video, 'Lo Heads everywhere lost their collective shit. There was certainly a double entendre in play when someone like Chef Raekwon mentions "snow" (nah, mean?), which we doubt Ralph Lauren originally had in mind. The outfit became so iconic that last year even Chris Brown wore it while performing on The Today Show last year. We're sure it went over the heads of the audience, but it was still one of Breezy's least douchey moments, so that counts for something.

Year: 1986

It doesn't get any crazier than this. It was 1986, rappers were in a music video with Aerosmith, rocking sneakers that they eventually got paid $1.6 million to wear. Moments like this are why a hip-hop trio could call themselves the kings of rock. In one fell swoop, they'd created a trend and asserted themselves as the most important act on the block, the boardroom, and the pop charts. Don't even think about putting laces in those shelltoes, either.