In hip-hop culture, the 80s were about trendsetting, innovation, and all out over-the-top style. From gold chains to Adidas to that mashed up hipster/punk/streetwear look, the 80s went from simple to totally crazy, and we are still obsessed with all of it because it gave us the first indication that music and fashion really do go hand-in-hand.
5. Salt N Pepa
Salt-N-Pepa started trends that have evolved through the decades, and have influenced artists like Mary J. Blige, Lil Kim, MIA, Santigold and Nicki Minaj, but also the everyday woman. From leggings with boots to jean jackets to big gold bamboo hoops, they created styles that are still cool today. They will likely most be remembered for the varsity-style leather jackets they wore in their "Push It" video, and while those may be a little less mainstream today, any young lady would still look hot wearing one in the club.
The Beastie Boys had a style that mixed graffiti with boomboxes, hipster with streetwear. They even threw in crazy items like fuzzy hats into the mix from time to time. Member Mike D would even go on to help found X-Large, one of the first and most influential streetwear brands. Fans loved the Beastie Boys' for their music, but they created a unique and innovative, yet timeless style that helped shape a culture. Boys who have never even listened to the Beastie Boys were probably still influenced by their style.
3. Big Daddy Kane
Big Daddy Kane was one of the first artists to popularize big signature jewelry pieces; from gold chains to nameplate necklaces, to massive four-finger rings. He was one of the founders of the "Bling Bling" craze that's still fashionable today, making it cool to wear nameplate necklaces and thick gold chains with everything, a tee and jeans to a crispy velour suit.
2. Slick Rick
Slick Rick's style was straight up crazy. His outfits were both classy and gaudy, from clean and smooth to bright and fun. And he spiced things up even further by adding a Kangol newscap, helping men learn how to look sharp, but not too fancy, at all times.
Like Big Daddy Kane, Rick wore a lot of gold jewelry, probably more than we've seen to date. Perhaps we can thank his awesome English accent and extremely clever lyrics and delivery, but Slick Rick's outlandish fashion statements were never "too much." They worked because he wore everything with confidence.
1. Run DMC
Run DMC had a totally iconic style. They put Adidas tracksuits and shell-toed sneakers on the map, even taking a fashion risk by wearing them laceless with the tongue out, forever changing sneaker culture.
They started out as unofficial brand ambassadors, but the whole Adidas thing became so popular that Run DMC and Adidas would go on to collaborate on many special projects. Adidas even has its very own "Run DMC" line. That's how innovative and memorable the rap trio's style is. We can thank the Run DMC/Adidas relationship for a lot of the collabs of the 2000s and 2010s like Kanye with Nike and Louis Vuitton or A$AP Rocky with Jeremy Scott.
And we definitely can't forget the thick-framed Cazals, leather blazers, Lee jeans, thick gold chains, and fedoras. They made it super dope to wear tracksuits with bling. Their style was never really "exreme" or "over-the-top," but they definitely created awesome looks that nobody else has come close to pulling off. Run DMC is undoubtedly the most iconic fashionable rap group in history. Period.
Like the 80s, the 90s were still about innovation and the introduction of new trends. From Versace to LA Raiders gear to a rap group logo that became a major fashion statement and a clothing label. The 90s were about groups and cliques, with members who had their own unique style. The decade also made 20s-era prohibition gangster fashion totally dope. Again.
NWA's style wasn't particularly memorable in the Slick Rick sort of way. They wore the gold chains made popular by Big Daddy Kane and Slick Rick in the 80s, but (from a fashion point of view) they will forever be remembered for starting simple and casual trends like t-shirts, crewnecks, flannels buttoned all the way up, snapbacks, and jeans. They also made it really cool to wear LA sportsgear like LA Raiders (the Raiders were in Los Angeles from 1982 to 1994 before heading back to Oakland) snapbacks and jackets. Through their style, they repped the West Coast proudly paving the way for guys like Snoop Dogg.
Snoop's style has certainly transcended through time, but it was born in the 90s. Along with Tupac, Snoop reinvented the 20s Prohibition-era gangster style: double-breasted suits, alligator shoes, silk shirts and fedoras.
But before Snoop flat ironed his hair and donned crisp suits, before he was a gangster, he was a gangsta. He took the NWA's West Coast style and added his own preppy touches. A typical outfit included a large button down flannel, Dickies with the cuff and the crease, a pair of Chucks, Nikes, or Jordans, and a flat bill cap.
Fans loved Snoop's West Coast preppy style so much that he wore a Tommy Hilfiger rugby shirt on a 1994 episode of Saturday Night Live and Tommy's sales exploded. Snoop Dogg gave Tommy's label street cred, sending the message to young men everywhere that Tommy Hilfiger was cool.
And we can't forget Snoop's hair, that was its own fashion accessory from cornrows to braids to perms to flat irons and back to braids. Not many guys could pull off pigtail braids the way Snoop could.
We've seen many artists' styles evolve through time, but not many have been as drastic as Snoop's. In the span of just a couple years, Snoop traded in the flannels, braids, and baggy pants for fancy suits, gator shoes, a flight iron, and a fedora. Whether Snoop was wearing a flannel and braids or a suit with a fedora, he always had that West Coast swag.
3. Bad Boys
Biggie, Puffy, and Ma$e all had style for days. With Versace shades, Coogi sweaters, and shiny suits, The Bad Boys had great individual style which also complemented each other very nicely. Biggie contributed to 90s fashion with Versace shades, colorful Bill Cosby-esque Coogi sweaters, Kangols, fedoras, suits, and so much more.
Puffy or Puff Daddy or Diddy, whatever you wanna call him, joined Biggie in making Versace and other designer labels cool and stylish. Together, the two were extremely instrumental in ushering in hip-hop's glamorous image.
In a way, one could liken Puff's style to that of Slick Rick's, going from classy to gaudy. The difference is, Puff Daddy was either classy OR gaudy while Slick Rick did both all at once. Puff could take a Versace suit and shades, leather pants, a Starter jacket or shiny suits and jerseys and still look stylish and put together.
Puffy founded his own clothing line, Sean John, in 1998. He is one of hip-hop's biggest style icons of all time.
From a fashion standpoint, Ma$e is probably most remembered for the shiny suits and jerseys he and Puffy wore in the "Mo Money Mo Problems" and "Can't Nobody Hold Me Down" videos respectively. In music videos, he and Puff often matched, and while their style was a little extreme, it served its purpose. In fact, the Shiny Suit Era ran for five years. It became so big, it was its own era. Like some other hip-hop fashion trends, shiny suits certainly aren't timeless, but they definitely helped define an era of more money, bigger music videos, and flashy clothes, and somehow, Ma$e actually made them look good!
Ma$e and Puff often dressed like twins, at least for videos, but let's not forget Ma$e's style. The white-on-white Air Force 1s, the puffy Northface, the Jesus piece, the hats...Often overlooked, Ma$e was definitely one of the most fashionable rappers of the 90s.
Simply put, the Wu-Tang Clan logo became its own iconic fashion statement, and grew to be so popular, it would lead to the creation of Wu Wear, the first of many clothing lines started by rappers. That alone gets the Wu-Tang Clan a spot on this list. Wu Wear was born in the mid-90s, but even today, men and women are rocking the iconic logo on everything from hoodies, jackets, t-shirts, and hats.
The group had its own fashionable rappers like Raekwon and Ghostface Killah. The rappers put Wallabees on the map. Ghostface even graced us with custom dyed Wallabees. Raekwon rocked the buttersoft leathers and sheepskins, and the Wallabees, but none of us will ever forget that "Snow Beach" Polo pullover he wore in Wu-Tang's "Can It All Be So Simple?" video.
Ghostace was definitely influenced by guys like Slick Rick and Big Daddy Kane, rocking the oversized accessories, but making the look his own with that gigantic eagle piece bracelet. His other contributions to fashion included knit hats and bathrobes, and of course those dip-dyed Wallabes. It's important to consider how much his style has evolved. When Wu first debuted he wore a stocking cap over his face, but over the years, he would go on to become one of the most fashionable rappers in history.
But while Raekwon and Ghostface were super stylish, they aren't the reason Wu-Tang is ranked #2 on this list. It's the iconic logo that so many of us are still rocking today.
Tupac was close friends with Gianni Versace. He absolutely loved dressing him, making him custom-tailored clothes. Tupac even modeled a gold suit at a Versace fashion show in 1996. Gianni Versace and Tupac have been described as "BFFs." A$AP Rocky has even said that Versace viewed Tupac as "the most beautiful man."
Tupac was definitely a style icon. Before he was a Versace model, he was rocking snapbacks, beanies, throwback jerseys, and no one will ever forget the bandanna tied into a headband-- that is perhaps how most of us imagine 'Pac when we think of his name. He stood out in the film Above The Rim in that unforgettable orange leather jacket.
Tupac's style took a more glamorous turn in 1995 with the velour shirt and snakeskin belt. In 1996, he and Snoop ushered in the 20s Prohibition-era gangster style. Whether he was wearing a bright denim jacket, a throwback jersey, or a double breasted suit, Tupac could pull off any look because he had swag. He helped remind us that style is about more than just clothes and shoes. It's a state of mind.
Honorable Mention: Will Smith
We couldn't keep Will Smith off this list, as his role in "The Fresh Prince of Bel-Air" gave him a huge following and cemented himself as a fashionista of sorts. His role as the Fresh Prince definitely helped curate what would became his staples-- colorful clothes (whether that be windbreakers, t-shirts, button downs etc), vests, snapbacks, Nike Air Forces and a high-top fade not only accurately sum up Will Smith as the Fresh Prince, but the general style of the '90s.
The 2000s paved the way for today's style, from making it acceptable to wear pink to bucket hats to the high-fashion white tee. We were introduced to Japanese fashion label BAPE, and clothing lines such as Billionaire Boys Club, Ice Cream, Benjamin Bixby, and more, were born. While the 90s made hip-hop glamorous, the 2000s took fashion to a whole new level, from streetwear to high fashion, trucker hats and tees to shutter shades and sick kicks, custom suits and pink minks.
T.I.'s style was iconic because, like Diddy, he could take it from casual to glamorous, and always look fly. With crisp suits, fedoras, and trench coats, he expanded on Tupac and Snoop's gangster look and made it his own. While his suit game was always sharp and crispy, we can't forget the perfectly angled fitted he wore in his "Rubberband Man" video.
He was definitely most popular for his suit game, but in 2008, along with Jason Geter, the Grand Hustle CEO founded a streetwear clothing line called A.K.O.O. In 2011, Tip's friend and labelmate B.o.B was announced as the "face" of A.K.O.O clothing.
4. Andre 3000
Andre 3000 was a lot like Slick Rick. He could wear the most extreme looks and somehow make it all work. He once covered a magazine dressed as an Egyptian Pharaoh, gold headdress and all. It was a little crazy, even for him, but like Slick Rick, no one questioned it.
At the 2001 VMAs, his Outkast brother Big Boi wore pink fur pants while Three Stacks wore a bright green and orange jumpsuit with a matching green hat. People couldn't decide if the look was dope or if the rap duo looked like "clowns." But like Puffy and Ma$e in the Shiny Suit Era or Slick Rick with the Kangols and extensive gold jewelry, Outkast made the look work. The only issue (and we would see this other times) was that their styles didn't really complement each other.
Andre made suspenders, knickerbockers, and straw hats cool. He could go from extreme to simple, from casual to fancy. In 2008, he founded his own clothing line called Benjamin Bixby. But the most impressive fashion contribution Three Stacks ever made was...making brown and black work together!
Cam'ron was one of the dopest dressers of the 2000s. Many of his crazy outfit choices helped pave the way for a lot of the high-fashion we see in hip-hop in today.
Cam made extreme clothing choices like pink mink, custom-made American flag patterned leather jackets that said "Diplomats," which he paired with a pink hat, monochromatic lime suits, and a long sweater that actually looked a lot like a dress. Perhaps we can thank that 2002 MTV VMA ensemble for that shirt-dress-thingy A$AP Rocky wore last year on 106 & Park, but more on that later. Cam made crazy fashionable choices that worked. For him.
But while Cam rocked pink mink, sweater dresses, and over-the-top leather jackets, he is also remembered for his sick throwback jersey game, and for making bucket hats cool. He is undoubtedly one of the biggest style icons of the 2000s.
2. Kanye West
Like Snoop and Tupac, Kanye's style has gone through many different stages. When he rose to prominence in 2004, he wore a lot of the popular trends of the time; baggy jeans, Nikes, and a Jesus piece. But he added his own unique touches such as pastel-colored rugby shirts and Polo Bear sweaters. Kanye was certainly not the first hip-hop artist to wear Polo or to even make it cool, but he did take crazy fashion risks like pairing one of those rugby shirts with a polo dress shirt and gold jewelry. So his claim that "Ralph Lauren was boring" before he wore him might have some validity. But Kanye's style has evolved so much through the years, there's really no sense in arguing that point. From prep swag to white dinner jackets with square-toed shoes and aviator shades to LRG, BBC, Bape, "shutter" shades and Crooks and Castles. Kanye could be preppy, hipster, or street. And he is a style icon because he could make any outfit in any of those genres look amazing.
We definitely can't forget Kanye's contributions to sneaker culture. His 2006 Nike Air 180 never hit retail, but they were definitely dope and proved that Ye had an eye for kicks as well as clothing. They combined black leather with a red Nike swoosh, cheetah print, blue accents, and the adorable College Dropout bear. He mixed street with high fashion in a shoe. Sneakerheads can still purchase a pair of Nike Air 180s on Ebay.
In the 2000s, both Kanye and Pharrell helped put Japanese streetwear brand BAPE on the United States map. In 2007, Ye collaborated with Bathing Ape on the Bapestas. Like the Nike Air 180s, the Bapestas had the College Dropout bear, but that's basically the only similarity. They combined red, brown, and tan, and of course featured the BAPE star. The Bapestas were the first Kanye-designed shoe to hit retail.
In 2008, Kanye's good friend Jay-Z collaborated with Reebok to create the S Carter CL Lows. Ye collaborated with Reebok and created four colorways for the Jay-Z-Reebok collab. In addition to his fun colorful twist, Kanye's version also featured the Late Registration bear.
In 2009, Kanye collaborated with Louis Vuitton on the Dons. There was no doubt before this that Kanye understood fashion and style, but his collab with Louis V solidified his place in the fashion world. Kanye's Louis Vuitton Dons would mark the first time a rapper would collab with a high-fashion luxury designer. The shoes were crazy expensive ranging from around $870 to $1140, but the high-fashion, haute-couture meets streetwear era was beginning, and Kanye capitalized.
Kanye's fashion and shoe game is still tight. He's still making dope collaborations with designers, and perfectly mixing streetwear with couture. He will forever be a style icon, and is one of the most fashionable men of all time, not only in hip-hop, but in the world.
Quite honestly, Pharrell could definitely be the most fashionable man on the planet. Like Kanye, he didn't just have dope style, he actually understood fashion from a marketing standpoint. He knew what he liked and he made it sell. But before Pharrell collaborated with BAPE founder Nigo to create Billionaire Boys Club and Ice Cream, he was "Skateboard P" rocking that bright yellow trucker hat, a logo tee, skinny jeans and Nike Dunks.
In some ways, Pharrell's style can be compared to Kanye's in that they both rocked streetwear and Louis Vuitton. They wore crisp suits, but they rocked BAPE hoodies and had a brilliant understanding of sneaker culture.
Throughout the 2000s, Pharrell was known for rocking so many different looks. He made it all cool from high-end to anime-inspired to trucker hats. Was he hipster, street, classy, high-fashion? Yes. Pharrell was all of it. It didn't matter what genre we saw him in, we were totally obsessed. And we still are.
Pharrell is probably most-remembered for putting BAPE on the map, and then for taking it a step further by collaborating with BAPE founder Nigo to create Billionaire Boys Club and Ice Cream. Like many of the rappers on this list, Pharrell's style is timeless and he could certainly have a spot on the 2010s list, but his style was born in the 2000s.
Pharrell's Billionaire Boys Club and Ice Cream lines continue to evolve. There's even a Billionaire Girls Club line also known as "BGC." One of the most unique things about Pharrell was that his style also influenced girls. He is quite literally the definition of a style icon.
The 2010s would see high-fashion, urban hipster, streetstyle, avant garde, and cutting edge risks come together. There would be more sneaker collabs, lions, gold chains, and even dresses.
5. The Cool Kids
The Cool Kids have heavily influenced fashion with their own brand of urban hipster. They can pair a $2 thrift-store-found t-shirt with a pair of skinny jeans, a snapback, and dope kicks. Back when they first started out in the rap game, around 2007, they mixed patterns and graphics, and looked just as stylish in a Coogi sweater or throwback jersey as they would in a colorful windbreaker a la Fresh Prince. Of course, both Sir Michael Rocks and Chuck Inglish's respective styles have evolved since then, but they are undeniably responsibly for bringing back the snapback from an era bygone. They wear what they like, and what feels comfortable, and that in it of itself has become its own trend.
They also made the bike culture cool in the hip-hop world. Sir Michael Rocks and Chuck Inglish did for bikes what "Skateboard P" did for skateboards. The Cool Kids remind us that style is about more than clothes and shoes. Style is a state of mind. Nowadays, you might catch Mikey wearing some over-sized wooden beads, graphic tees/sports jerseys and/or Hermes sweat suits, plus some Cartier shades-- an eye wear staple that is also making a comeback these days.
Theophilus London's unique style mixes tailored pieces with high-end streetwear. While it's hard to define his style, there is no doubt that he is one of the most fashionable men of the 2010s. He even has his own clothing line, LVRS, which has collabed with brands such as Surface to Air, 40 Oz NYC, and Del Toro. He and designer Cole Haan also collaborated together on a pair of blue suede shoes, mixing retro and modern swag and creating something beautiful.
Even Chanel's Karl Lagerfeld loves Theophilus London's style, and has photographed London wearing Chanel. Theophilus London and Karl Lagerfeld might be the Versace and Tupac of this generation.
Theophilus London isn't the first rapper to mix high-fashion with streetwear, but he does it differently than his predecessors. He'll rock a blazer with a snapback and a pair of Jordans. His style is classic, yet contemporary.
Wiz Khalifa is one of the most fashion-forward rappers in history. Sometimes he keeps it simple with (extremely skinny) jeans, a tee or tank, and a vest, while others, he goes for a more Jimi Hendrix-ish psychedelic look. He has a very versatile style that is not always relate-able: when he revealed the album cover for O.N.I.F.C., many fans scratched their heads, yet to the high-fashion world, the look he rocked was dope.
His tattoos and bleach streak have also become fashion accessories in their own right. He can go shirtless with a pair of jeans, a dope belt, and Chuck Taylors, and still look awesome because his body art is a fashion statement alone.
Wiz is undoubtedly best known for his love of Chucks. He even collaborated with Converse in 2013. Khalifa has loved the "clean and classic" look of Chuck Taylors since his high school days, and actively expressed his excitment to collab with the brand. The shoes in the Wiz Khalifa collection stay true to Chuck Taylor's iconic classic design that Wiz loves so much, but the Taylor Gang leader added his own accents, such as the signature Wiz Khalifa logo tab, to express his own creative vision. The collection epitomizes Khalifa's style; classic and simple with a splash of bold and eclectic.
2. Big Sean
Big Sean is one of the most fashionable men of the 2010s. He helped take the clothing brand TI$A to great heights, as well as make the Starter jacket cool again. Big Sean took the 90s West coast style of the NWA with the snapbacks and the Starter jackets and put his own unique high-fashion spin on it. He took the snapback and put his own sophisticated touches, like snakeskin, on it.
He shows his lifelong love of 90s hip-hop by wearing Biggie and Tupac tees, but he does it with style and elegance, not in the extremely tactless way Miley Cyrus "showed appreciation" this year at the MTV EMAs.
Sean can wear a tux or a Supreme flannel and still look super dope. He has a unique sense of style that is perfectly represented in his Aura Gold clothing line. Founded in 2013, Aura Gold clothing reflects Sean's love of athletic and vintage. Aura Gold is sporty yet elegant, a look not many can pull off. He reps the Finally Famous crew with sophistication using what has become an iconic lion logo.
Sean's Aura Gold line features tees and hoodies that "real people" would actually want to wear. He took his own creative vision and turned it into something truly remarkable. Many rappers have created their own clothing lines, but not all of them have had Sean's true attention to detail and business sense. When Aura Gold was his first released, Sean didn't personally love every piece of clothing, but he understood that the public would. He understood that he had to put his personal tastes aside and make a business decision.
In addition to Aura Gold, Sean heavily reps the #BeenTrill clothing brand (as does his label head Kanye West), and has recently hinted at a possible collaboration.
1. A$AP Rocky
A$AP Rocky is the most fashionable rapper of this decade, and one of the most fashionable men in the world today because he takes risks. At the 2013 BET Cypher Joell Ortiz rapped that he never expected to see a fellow rapper in a dress. He was talking about this shirt-dress-thingy A$AP had previously worn on 106 & Park. It was different, it was bold. A$AP breaks fashion rules and makes his own. And while not everyone can get behind the dress, we can all agree that the man has a unique style.
A$AP Rocky has taught us many lessons about fashion. For instance, you can wear all white or long Johns with shorts and a quilted bomber jacket, and all you need is a pair of Timbs to balance the look. On a related note, it's not very easy to pull off some of Rocky's layered ensembles. Start slowly and don't forget your Timbs.
The "Fashion Killa" rapper also reminds us to pick a brand we love and rep it to the fullest. For A$AP Rocky, that brand is HBA (Hood by Air). He also rocks Supreme, but not as hard. His HBA pieces might be a little too daring and avant-garde for some of you. The lesson here: Rocking a bunch of expensive brands doesn't make you look cool. Loving your clothes, feeling good in them, that's what's dope.
For you sports fans out there who are wondering how to rep your favorite team and still look fly, the biggest fashion mistake you make is wearing the jerseys of current players. Nah, homie. If you want to look as dope as A$AP Rocky does, you've got to understand that sports and high-fashion meet in a beautiful place called "throwback jersey" land. A$AP Rocky not only understands throwback jerseys, he makes them elegant and luxurious by adding python skin to the logo, number, and name like on his Chicago White Sox Bo Jackson jersey. Now, you could probably wear a Bo Jackson White Sox jersey and still look dope. But Rocky's sophisticated accents certainly don't hurt. See also: his retro Chicago Blackhawks jersey. On a related note: this also applies for wrestling shirts. By wearing a D-Generation X jersey, Rocky proves that it's not nerdy to be a wrestling fan. You just have to know how to express your love.
We've also learned that it's great to be adventurous with fun patterns and crazy looks, but keeping it elegant and sophisticated with a simple black shirt and pants and a few gold accents looks pretty dope as well.
In September 2013, A$AP Rocky collaborated with his friend, designer Jeremy Scott, on a pair of Adidas. The JS Wings 2.0 "Black Flag" wings are a long way from the shelltoe Adidas Run DMC made so popular in the 1980s, but the collaboration proves that it's stylish and admirable to take a lesson from those before you, and collab with a designer or company you believe in.
The most important lesson we can take from A$AP Rocky's adventurous fashion choices is to dress how YOU want. He can perform in a jumpsuit and look awesome because he owns the look. Not everyone can pull off a lot of Rocky's risky looks because they're not confident enough.
You might not love all the ensembles or looks or fashion choices of the rappers on this list. And that's fine. Style isn't just about clothes and shoes. Style is a state of mind, and every rapper on this list proved that with their own unique vision.