Since hip-hop’s earliest pioneers, the secondary role of a rapper was being fluent in the jargon of floss and adept at the art of stunt. Hip-hop fashion has gone through many different phases. In the late ‘70s and ‘80s afrofuturistic and B-boy looks were celebrated. Then throughout the ‘90s, we saw both the rise of gully looks inspired by street life and exorbitant outfits like shiny suits and pimp coats. Within the past two decades, hip-hop fashion collided with skateboard culture and even avant-garde fashion. It’s undeniable that hip-hop fashion has deified and defined modern American style. So here we take a look at the most stylish rappers of all time.
Height of Style: In My Mind Tour
Signature Look: Forward-looking streetwear.
Pharrell is your favorite stylish rapper’s favorite stylish rapper. His approach—understated cool, with offbeat and witty accents—influenced EVERYONE; Jay, Kanye, Pusha T, and just about all the new school rappers owe him a debt. Pharrell pioneered nerd couture in opposition to hip-hop fashion hegemony and made it okay to wear high-end, skate park, anime-influenced accessories in bold colors and still be rap certified. He was onto A Bathing Ape early and established a continuing relationship with streetwear legend Nigo that led to his Billionaire Boys Club and Ice Cream brands. Even in his N.E.R.D. days, Pharrell harnessed the power of the collab, creating limited-edition items with Nike, BAPE, Medicom, and more. In more recent years, he’s boasted an ongoing relationship with Adidas resulting in a wide array of original sneakers and even dropped his own Chanel collection in 2019. These days, you would hard-pressed to find him not repping his friends lines, whether that’s Human Made, his joint venture with Nigo, or Cactus Plat Flea Market, Cynthia Lu’s collection. To top it all off, the man has barely aged a day since his days of dressing in head-to-toe Bape. That was over a decade ago. It probably isn’t a stretch to call Pharrell one of the coolest people ever. And his style is a big part of that.—Rob Marriott
Outkast: Andre 3000 & Big Boi
Height of Style: “Hey Ya” video
Signature Look: Throwback dapper gentleman.
Since arriving on the scene in the late ’90s alongside Big Boi, Andre 3000 reconfigured a Funkadelic style that drew heavily on George Clinton, Bootsy Collins and Afrika Bambaataa. Ever the contrarian, Dre has experimented with turbans, blond wigs, shoulder pads, a modernist take on Nat King Cole, and barbershop quartets. As time passes, Andre 3000, who went on to launch a retro-preppy brand called Benjamin Bixby, is in the public eye less and less. His style has settled down a bit. He opts for essentials like beanies, solid-colored crewnecks, and trousers more often than not, but he still has his moments. Who could forget the black jumpsuits adorned with various phrases like, “everything is temporary” and “thinking deeply about shallow sh#t,” that he rocked with a platinum blonde wig during Outkast’s reunion tour in 2014? Three Stacks, who would also work with Tretorn on a footwear capsule, still knows how to make a statement when he wants to. And his style has lived on thanks to Instagram mood boards reminiscing on his obscure Aughts fashion choices. Real icon status.—Rob Marriott
Height of Style: “So Fresh, So Clean” video
Signature Look: Gator belts, minks, white tux
Even though his flamboyant and daring partner Andre 3000 gets more attention for being a style star, Big Boi’s look is just as impressive because he stays fresh without going overboard. He found his own lane combining southern gentleman suits with trap-star standards like jerseys and baggy fits.—Rob Marriott
Height of Style: Watch the Throne Tour
Signature Look: Yankees fitted, spread collar shirts with jeans, All Black Everything
A look across Jay-Z’s 24-year career is like looking at the evolution of hip-hop fashion. The introduction of platinum, the full embrace of throwback jerseys, the re-introduction of Gucci sneakers in the form of his Reebok S. Carter line, the end of car rims, rocking collar shirts with jeans, the dawn of All Black Everything, and so on. Oh, he also, “made the Yankee hat more famous than a Yankee can.” In his later years, he hasn’t been afraid to embrace new trends. Whether he’s rocking Fear of God or a streak of Rhude fits while sitting courtside in early 2020, Hov always looks current and June Ambrose, his stylist, keeps him looking clean. And what about the colorful suits he’s worn alongside wife Beyoncé during the On the Run tour. Everyone always talks about Kanye’s style evolution from year-to-year. Well, his “Big Brother” Jay-Z’s versatility might be just as impressive.—Rob Marriott
Playboi Carti
Height of Style: “Magnolia” video
Signature Look: All Rick Owens everything
From his start as a Soundcloud darling draped in rare Supreme to the Rick Owens obsessive he has become during his more recent baby voice era, Playboi Carti has always been about his style. There’s a reason Virgil Abloh recruited him to walk in Off-White and Louis Vuitton runway presentations in the past. While Carti’s fit pic archive showcases everything from vintage Vivienne Westwood to slouchy Raf Simons sweaters, his style magnum opus has got to be the video for his 2017 hit single “Magnolia.” In the 3 minute and 24 second spectacle he was maneuvering (or Milly Rocking, if you will) around New York City in fire pieces like Supreme basketball jerseys and polka dot button-ups, archive Issey Miyake, and Rick Owens Ramone sneakers. Sure, fans are still patiently waiting for Whole Lotta Red to drop, but at least Carti has kept his gear consistent during his extensive period away from the musical spotlight. —Mike DeStefano
Lil Yachty
Height of Style: Lil Boat 3 era
Signature Look: Vintage streetwear and rare sneakers
Lil Yachty has gone through a few transitions since catching people’s attention back in 2016 with his breakout single “One Night.” Rather fittingly, he helped usher in a short-lived revival for Nautica as a nod to his nautical name, which even resulted in an official partnership and multiple capsules of collaborative apparel in 2017 and 2018. Nowadays, it’s no surprise to see Lil Boat rocking a bubblegum-colored Bape Camo hoodie from the 2000s (he also has worked with the brand) and a super rare pair of sneakers that he paid thousands for like Kanye West’s Reebok S. Carter collaboration or OG Air Jordan Is from 1985. His jewelry game is just as impressive with custom pieces ranging from rainbow-colored grills to a $100,000 diamond-encrusted Bart Simpson pendant donning his signature red braids—it’s an homage to Gucci Mane’s Bart chain. He’s also has no problem supporting up-and-coming designers, too, a nice change of pace from the all designer everything many rappers abide by. Yachty cares about fostering the youthful community he’s a part of. The best part about Yachty’s style is how authentic it is to his persona. It looks like the 22-year old is just buying everything he wanted to while he was growing up and rocking it with pride. Is he a shopping addict? It’s possible. Is that a problem? Absolutely not. His passion for collecting his personal grails is obvious and you have to commend that. —Mike DeStefano
Ghostface Killah
Height of Style: Supreme Clientele
Signature Look: Knit hats, bathrobes, massive eagle bracelet, Wallabees
Pretty Toney took the Slick Rick approach to oversized accessories and made it his own. The bathrobe and massive eagle piece bracelet were tame style choices compared to the stocking cap he rocked, which was pulled over his face, when the Wu-Tang Clan debuted. But Ghostface’s most important contribution to fashion will always be the custom dyed Wallabees. You don’t just name your album Wallabee Champ and refer to yourself as the “Wallabee Kingpin” for nothing. Monica Morrow, his stylist, and her teammate, Boz, would run around New York City trying to bring Ghostface’s visions to life. “Ghost was very involved. You weren’t doing anything without him being involved in it,” says Morrow. Morrow says he would give her loose instructions. “He would say, ‘I want a robe that looks like a fax machine,’ or ‘I want glasses that look like I’m looking out of a window in Paris,’ and I would just have to figure it out.” And she did. Have you seen the “Cherchez LaGhost” video? It’s a masterclass in styling an artist as creative as Ghostface.—Aria Hughes and Rob Marriott
Height of Style: “C.R.E.A.M.” video
Signature Look: Polo, Buttersoft leathers and sheepskins, Timberlands, and Wallabees
In the grimy 90s, Rae’s eye for detail made him a style leader in the Wu-Tang Clan. The Buttersoft leather king kept his hair waves precise and took his sartorial cues from the NYC drug lords. Perhaps his singular most iconic style moment was when he rocked the Polo Ralph Lauren Snow Beach pullover in 1993’s “Can It All Be So Simple” video. The piece is so legendary that Ralph Lauren even brought it back in 2018 with an official retro release. And The Chef is a big reason why. Of course, the footwear was always on point too as Rae kept a steady rotation of New Balance runners, Timberlands, and Wallabees laced up at all times. He’s been given his flowers from the streetwear community over the years, appearing in LRG and Kith campaigns, and collaborating with footwear brands like Saucony, which were inspired by his classic Only Built for Cuban Linx album (aka The Purple Tape). He also appeared on one of the most iconic Supreme T-shirts of all time alongside Elmo and an uzi. Morrow styled Rae as well. “Let me say something about Rae, he can dress his ass off,” says Morrow. “So once again, I was the executor. He knew exactly what he wanted, I just helped him achieve it. But he had an incredible sense of style.”—Aria Hughes and Rob Marriott
Lil Uzi Vert
Height of Style: Instagram circa 2019
Signature Look: The best designer pieces that money can buy
While many rappers boast about their lack of a stylist, you cannot have “NO STYLIST” as your name on Instagram without doing some serious dressing. And Lil Uzi Vert definitely does. His shopping habits are said to be stuff of legend. Plenty of people talk about buying the whole store—one friend told GQ in 2018 that he is, “literally spending house money on clothes.” Uzi really lives that life. The Philadelphia native is always stepping out in the flyest designer fashion. Perhaps the most obvious examples came back in 2019 when Uzi flooded his Instagram with fire fit pics, which have now been deleted. He was wearing everything from vintage Bape at the dentist’s office to full Prada suiting or Louis Vuitton pieces designed by Virgil Abloh. Even before his style renaissance, Uzi was making waves with his gender fluid, rockstar style. He was going viral in Faith Connexion and $2,400 Valentino blouses. Whether you love it or hate it, he doesn’t care. He had the perfect response to his critics during a 2017 interview at the Billboard Music Awards: “They never felt these fabrics before.”—Mike DeStefano
ASAP Rocky
Height of Style: “RAF” video
Signature Look: Anything. Literally anything.
The Fashion Killa. Pretty Flacko. Rocky. Whatever you call him, ASAP Rocky has been comfortably sitting at the top of many best dressed lists since entering the scene back in 2011. And for good reason. His “Peso” video fits are still legendary. He mixed zany Jeremy Scott x Adidas sneakers and a Supreme leopard towel draped over his head with luxury pieces from Raf Simons and Rick Owens. He loved the Belgian designer so much he even made an anthem for him in 2017 complete with a video inspired by Simons’ video lookbook for his debut collection. He became a face of the “street goth” wave that soon followed by helping catapult brands like Been Trill, Hood By Air, and Black Scale. As his career progressed, he leaned more into the luxury lane becoming the face of Alexander Wang and Dior campaigns. These days, it’s just as normal to see him in a vintage T-shirt and Needles track pants as it is to see him in a full Prada suit. There’s literally nothing he can’t wear. Case and point, he turned babushkas, a head scarf traditionally worn by Russian and Polish grandmothers, into something kids in SoHo wanted to pull off. He said it best himself on “Brand New Guy,” “Fuck fly/I am fashion.”—Mike DeStefano
Kanye West
Height of Style: Paris Fashion Week Fall/Winter 2010
Signature Look: Pink polos, Shutter Shades, leather kilts, Adidas Yeezys, earth-toned everything
“I have so much to stunt about,” proclaimed Kanye West (aka Martin Louis The King Jr.) in the middle of a Paris hotel room to officially announce his Louis Vuitton sneaker collab back in 2009. That sentence depicts Kanye West’s style history in a nutshell. Since wearing a “pink ass polo and a fuckin’ backpack,” when he first came out, Kanye has moved the needle of hip-hop fashion with his everchanging wardrobe. The Shutter Shades in the “Stronger” video. His all-red suit to debut “Runaway” at the 2010 MTV VMAs. The leather kilts and Givenchy T-shirts during the Watch the Throne era. Margiela face masks on the Yeezus tour. Wearing distressed denim to the Met Gala. All legendary moments. And that is barely even scratching the surface. Nearly anything he’s worn has trickled down onto fast fashion shelves. Perhaps the most obvious example being his “homeless” Yeezy Season style that included earth-toned hoodies, tattered T-shirts, and baggy sweatpants. Tour merch, he made that a hot commodity too with thought out designs for his Yeezus and The Life of Pablo tours—people wrapped around blocks just for some Gildan.
His Yeezy sneakers, which began with Nike in 2009 and have since turned into a multi-billion dollar empire with Adidas, are some of the most important shoes ever released. Following Jay-Z’s deal with Reebok, Kanye helped cement the precedent that shoe deals weren’t just for athletes anymore, a trend that’s continued with people like Travis Scott and Virgil Abloh (who both came up under Kanye). Now he’s working with Gap, which will likely be his most readily available apparel to date. As polarizing as he is for so many, his style legacy is Hall of Fame level. As he echoes on the Cruel Summer cut “Cold,” don’t talk to him about style, he will embarrass you. —Mike DeStefano
Travis Scott
Height of Style: AstroWorld era
Signature Look: His own Cactus Jack merch and a pair of Nike SB Dunks
Few rappers are as influential as Travis Scott when it comes to style right now. Every pair of Nike SB Dunks he wears skyrockets in value. He’s almost single handedly responsible for the Nike subdivision’s resurgence over the past two years. Every single one of his Nike and Air Jordan sneaker collaborations sells out within minutes. And his insane amount of Cactus Jack merch drops are start to feel less like typical artist merch and more like pieces from a lifestyle brand. All of this is La Flame at the height of his influence, but his personal style has been evident since the Owl Pharaoh days. Back then it would be commonplace to see him in Air Jordan IVs, leather pants, and a vintage Supreme Box Logo T-shirt. He walked in Mark McNairy’s New York Fashion Week runway show back in 2014 too, long before his star status was fully realized. He was one of the first people spotted in the highly-coveted Louis Vuitton x Supreme collection during Paris Fashion Week in 2017. He’s had official collabs with Ksubi and Helmut Lang. And he has an Evisu denim project (another 2000s trend he has helped bring back) on the horizon. He’s been the face of campaigns for Saint Laurent and Dior. The list goes on. Love him or hate him, you don’t get all of these looks if you dress poorly. If there is one person who embodies the style of the youthful streetwear scene in 2020, it’s Travis. And it doesn’t seem like that will change any time soon.—Mike DeStefano
Slick Rick
Height of Style: “Children’s Story” video
Signature Look: Assorted eyepatches, Justice scales on dookie gold rope chains, multiple rings, furry Kangols
Rick’s truly original amplification of British Jamaican rudeboy style turned hip-hop on its ear with his Bally shoes, furry Kangols, and cardigans draped in enough gold for an Ashanti King. Whereas Mr. T’s layered jewelry came off as corny at times, Slick Rick’s never looked out of place. It just worked. His influence is far-reaching—rappers as diverse as Tupac Shakur and Ghostface took meticulous notes. He was ahead of his time, a forefather of bringing luxury fashion into the hip-hop scene and obsessing over gaudy gold chains and rings as a go-to accessories. One style choice that no one else has been able to duplicate? His signature eyepatch.—Rob Marriott
Dipset: Cam’ron, Jim Jones, & Juelz Santana
Height of Style: Purple Haze Era
Signature Look: Pink fur
Killa Cam’s general “middle finger to the world” attitude somehow blossomed into one of the most unique uses of color in hip-hop history. Harlem’s penchant for flash and pastels reaches back to Teddy Riley and beyond, but Cam’ron took it to a new extreme resulting in an explosion of pink and fur and a Range Rover to match. Stylist Monica Morrow influenced Cam to try out the shade. “Cam wanted to do something different,” says Morrow. “And I thought, ‘Let me try pink.’ If anybody could pull it off, it was Cam. He was a pretty boy, but you don’t get more masculine than Cam. So we tired it and he loved it.” Morrow says that led to brands like Pelle Pelle making pink jackets. Quite frankly, Killa Cam’s cotton candy-colored fur fit from the Baby Phat fashion show in 2003 is one of the most iconic in hip-hop history. The Dipset member was also responsible for pushing the boundaries of custom jewelry in the Aughts with pieces like his motor-operated, Scarface-inspired globe pendant and color-changing stoplight still considered to be some of the best customs to ever swing from a rapper’s neck. Pelle Pelle leather and throwback jerseys, Cam was on that wave, too. If you want to know how rappers dressed two decades ago, he was the blueprint.—Aria Hughes and Rob Marriott
Height of Style: “Dipset Anthem” video
Signature Look: A bandana headband, Ed Hardy T-shirt, BB Simon belt, and baggy denim
Juelz Santana’s American flag fit in the “Dipset Anthem” video. That’s really all the evidence needed to verify the Dipset member’s place in hip-hop fashion history. The look is so iconic it even inspired one of the most coveted Supreme Box Logo hoodies that released back in 2014 and a patriotic Timberland collab in 2017. But if you need more evidence, just look at his signature rockstar-inspired looks from the Aughts. His colorful collection of studded BB Simon belts was legendary and paired perfectly with his gaudy Ed Hardy T-shirts. Chrome Hearts is the it brand of the moment. Well, Juelz was rocking it over a decade ago. Along with his fellow Diplomats Cam’ron and Jim Jones, Juelz represents an era of New York fashion, one whose influence is still prevalent in city to this day.—Mike DeStefano
Height of Style: Diplomatic Immunity era
Signature Look: Ed Hardy, BB Simon, scarves, and skulls
Like Cam’ron and Juelz Santana, Jim Jones is another Dipset member who has become known for his style. He’s maintained Harlem’s tradition of flash with everything from Arab style scarves to blingy skull and bones belt buckles (before Lil Wayne followed suit). Other things Jim takes credit for in hip-hop style: Pink (the color), button-up shirts, and tailored suits. The Sneaker Shopping alum also taught us how to properly “tongue fuck” our Air Jordans, a style move that should be in anyone’s arsenal. He’s even been able to turn his love for fashion into his own line, Vampire Life. In other words, he’s ballin…—Rob Marriott
Young Thug
Height of Style: Jeffrey Era
Signature Look: Dresses, slim fits, and high fashion.
When it comes to style, anything goes for Young Thug. One minute, he’s wearing a dapper all-white fit embellished with bondage-inspired accessories by BOND Hardware. The next minute, Thug is wearing a Supreme fur varsity jacket with fleece shorts because in Thug’s world, seasonal temperatures are simply a construct. The Atlanta rapper has always been about wearing whatever he wants despite what anyone thinks. Throwback to 2016, back when Thugger was puffing a blunt while adjusting a model’s look on the VFILES runway, and donning an Alessandro Trincone dress on the cover of Jeffery. Supposedly, Thug wore the dress because he had to hide a “motherfucking AK-47 up under it.” But even when the internet clowned the look at the time, Thug was really carrying on the style legacy of other ATL greats such as Andre 3000 and Cee Lo, who’ve also rocked some ill dresses over the years. As Thug famously declared in a spot for Calvin Klein: “You could be a gangster with a dress, you could be a gangster with baggy pants.” —Lei Takanashi
Tyler, The Creator
Height of Style: From Odd Future to Igor
Signature Look: Supreme, GOLF, pastel colors
Any teenager who grew up during the Odd Future era of Tyler, the Creator’s career knows exactly how impactful the West Coast rapper’s style was. Although Supreme was a well recognized streetwear brand already, it’s undeniable that Tyler exposed the brand to millions of teenagers during the early 2010s. From wearing a blue box logo hoodie in “She” to having the entire OF crew wearing new Supreme five-panel caps in “Oldie,” practically every video Tyler released during this time advertised Supreme in some way. The rebellious attitudes of both entities synced perfectly together and Tyler and his crew held a James Dean-like influence on a generation of angsty teenagers. Eventually, Tyler leveraged his influence into promoting his own streetwear brand GOLF, which he exclusively wore for a number of years. But like his own music, Tyler’s taste in clothing has matured since those Odd Future days. Since releasing Igor, Tyler looks less like a Fairfax skate rat and more like an old college professor. —Lei Takanashi
A Tribe Called Quest
Height of Style: The Low End Theory-Midnight Marauders
Signature Look: Athletic caps, Dashikis, Normcore.
Within the flashy world of hip-hop, there aren’t too many crews like A Tribe Called Quest. Despite the fact that ATCQ were the first rappers to receive the gilded “Five Mics” rating by The Source for their debut album, the group carried themselves like the everyman—which probably explains why they made an entire song about losing a wallet in El Segundo. Granted, Q-Tip had a Tommy Hilfiger piece or two, the members of ATCQ weren’t really about rocking Cuban links or owning the flyest ‘90s gear that money could buy. A regular denim shirt, baggy jeans, a plain hoodie, and a baseball cap was really all the group wore when it came down to clothes. Of course, since the group was down with the Native Tongues movement, they also proudly rocked dashikis and other Afrocentric looks during their heyday in the early ‘90s as well. But when it comes to picking the most stylish member of Tribe, it was undeniably the late Phife Dawg. A fan of sports snapbacks, Starter jackets, jerseys, and New Balance sneakers, Phife truly made that laidback athletic apparel of the ‘90s work for him. Just peep this fit he wore for this performance on the The Arsenio Hall Show, where he perfectly matches a classic Team USA jersey with a pair of red and white Air Force 1’s. Rest In Power to Malik, the five-foot freak.—Lei Takanashi
Westside Gunn
Height of Style: Pray for Paris
Signature Look: Trench coats, sports jerseys, and fly designer.
There’s only one FlyGod. Aside from ASAP Rocky, it’s highly likely that Westside Gunn is the only rapper on this list who has name-dropped every brand currently stocked at Dover Street Market or SSENSE today. You’ll honestly be hard pressed to find another rapper who could spit a verse about Mac-10s and Feng Cheng Wang trench coats over a Preemo beat. Considering that Griselda was originally supposed to be the name of Gunn’s clothing label, it’s not surprising that he is passionate about fashion. But what makes Gunn unique is that he’s willing to pull off looks others wouldn’t dare to try. Who else is wearing a customized San Jose Sharks hockey jersey for Louis Vuitton’s runway show or a one-of-one KidSuper jacket for Griselda’s debut appearance on late night television? No one but the FlyGod himself. “I can’t speak for nobody else because I was always a trend setter,” Gunn told Complex. “I always just studied fashion and what people wore. What was the newest thing and what was the newest thing coming out? I always wanted to just stay 10 steps ahead of everybody. It’s just been like that my whole life.”—Lei Takanashi
Height of Style: Livin Large–Nuttin But Love
Signature Look: Suits, Nikes, and glasses.
Before Biggie Smalls, before Big Pun, and before Rick Ross, there was Heavy D. When Andre Harrell tried to convince Russell Simmons to sign the “overweight lover” to Def Jam in the mid-80s, Simmons rejected his offer because he believed that know one would support an overweight rapper. Harrell called Simmons bluff by forming Uptown Records, signed Heavy D and the Boys as the first group on his new label, and made Heavy one of the first plus-sized rap stars. “The first thing I noticed about them [Heavy D and the Boys] were that their haircuts were so immaculate,” said Harrell in an interview shortly after Heavy D’s death. “He [Heavy D] was a style guy. He didn’t want you to think of him as a fat boy.” Heavy D became revered for his love songs and presented himself like a dapper gentleman early on by wearing full suits while also staying true to ‘80s hip-hop style with the gold rope chain and the oversized shades. He was also up on ‘80s trends like Coca-Cola rugbys and was clearly a huge sneakerhead. Heavy dedicated a song to Nike on his debut album and even wore newly released Air Jordan IIs on the cover of his 1987 album Chunky But Funky. But never forget that moment in the music video for “Money Earnin’ Mt. Vernon” when a sneaker salesman approaches Heavy D with a stack of red Nike shoe boxes and leaves one Reebok box on top. Our mans Heavy already knew that it was Swooshes over ‘Boks all day. He really tossed that Union Jack shoe box over his head to get to the real goods.—Lei Takanashi
Biggie Smalls
Height of Style: “Hypnotize” video
Signature Look: Coogi sweaters, double Jesus pieces, custom suits, fedoras, apple jack hats, and Versace Sunglasses
Biggie went from playing dice in Timbs on the streets of Brooklyn to rocking Mafia-esque suits with Puffy at the 1997 Soul Train Awards. The garments Biggie wore, such as colorful Coogi sweaters and leather Avirex jackets, defined ‘90s hip-hop fashion at its finest. Always seen wearing a pair of Versace shades, Biggie introduced hip-hop to the brand decades before the Migos made an anthem about it. Even Donatella Versace herself has acknowledged that the masses learned about Versace because of Biggie. But If we’re talking about Biggie’s style, a lot of credit has to go towards his stylist Groovy Lew. According to interviews, Lew said Biggie’s style was originally “straight, dirty, Brooklyn” and that he had to get Versace pieces specially tailored for the rapper because European brands never released clothing in sizes that large. Years later, it’s clear Biggie was miles ahead of the game. What other rapper was wearing Bathing Ape jackets in the ‘90s? Case closed.—Lei Takanashi
Height of Style: “Going Back to Cali” video
Signature Look: Kangol bucket hats, gold rope chains, and TROOP gear.
LL Cool J understood the art of branding from the very beginning. His red Kangol, if not completely original, became his trademark—along with his “don’t fuck with me” muscles. From TROOP gear to custom Gucci tracksuits by Dapper Dan, LL Cool J was at the top of the hip-hop fashion game throughout the ‘80s. The following decade, he could be seen rocking North Face Gore-Tex pieces from head to toe and accidentally launched some of his own fashion trends—turns out that he always rolled up one pant leg because he just wanted to give his large left calf muscle some air. As hip-hop grew, LL went from rocking the freshest brands to landing spots in FUBU print ads—he invested in the brand—and iconic Gap television spots. Nowadays, LL is chilling and trying to carve his own lane in the world of streetwear with his brand Rock The Bells. Monica Morrow started styling him on the G.O.A.T. album, and had a full circle moment while working with Armani on the suit he wore to receive his Kennedy Center Honors Award in 2017. “Back then people would be like, ‘No, they don’t fit our brand,'” says Morrow. “They wanted to look at lyrics from songs back then. And a lot of times they would say no after they saw the lyrics.” For the Kennedy Center Honors Award, someone from Armani flew to New York to design the suit with Morrow. How things have changed.—Aria Hughes and Rob Marriott
Height of Style: Tha Carter III-Tha Carter IV
Signature Look: Dreads, full body tatts, ice grills, bright sneakers
Whether he was wearing camo Bathing Ape hoodies, simple white tank tops, or just going shirtless with saggy jeans, Lil Wayne was a pioneer when it came to not giving a Weezy F when dressing up. Since being a young Hot Boy prodigy, and coining himself “the best rapper alive” on Tha Carter II, Lil Wayne carved out a truly unique sense of style for himself. The peak of Lil Wayne’s daring fashion sense really surfaced in the late 2000s and early 2010s. This was back when Weezy wore animal print jeggings with Murakami LV belts or dressed like a lost skateboarder inside a shopping mall. Although he was clowned for co-opting skateboarding at the time, Lil Wayne ignored all the haters and eventually launched his own skateboard brand, Trukfit, while getting somewhat decent at skating. To this day, his fashion sense hasn’t changed much. You can still catch Weezy wearing sunglasses, a fitted cap, and some very colorful pieces. BAPE even acknowledged the influence Lil Wayne had rocking its colorful camouflage hoodies back in the day by making him the face of their 2019 Ugg collaboration—which also officially made Weezy the only rapper who can make a pair of Uggs look hella fresh. Weezy has always remained true to his own style and you can never knock that.—Lei Takanashi
Lupe Fiasco
Height of Style: 2012
Signature Look: Wire frames, varsity jackets, crewneck sweatshirts, Nike SB Dunks, Gucci accessories, and Japanese fashion.
Aside from Kanye West, Lupe Fiasco is one of the more fashion forward rappers to come out of Chicago. While Kanye made it alright to dress in rugby shirts and other preppy classics, Lupe was one of many rappers who made skate fashion more acceptable for the next generation of hip-hop. After growing out of varsity jackets and crewnecks, Lupe developed an interest in more avant-garde fashion during the 2010s. He could be seen attending Yohji Yamamoto Y-3 runway shows or even wearing archival Vivienne Westwood pieces during this time. In an interview with Complex in 2012, Lupe listed Junya Watanabe, Rei Kawakubo, and Mihara Yasuhiro as his favorite Japanese designers—and even predicted the future popularity of Chrome Hearts. While most rappers make one brand, Lupe attempted to build three, which included Trilly & Truly, Righteous Kung-Fu, and Overthrow. Recently, Lupe’s dropped a single titled “Shoes” that features Virgil Abloh.—Rob Marriott
Height of Style: Raising Hell Tour
Signature Look: Oversized Cazals, black Fedoras and Kangols, gold rope chains, black and white Adidas Superstars
Run-DMC’s minimalist approach made the whole group larger than life. They proved that less is more, and maybe even meta. The single gold rope chain against all black tracksuits represented the boldness of that style. The crew’s love for Adidas Superstars eventually led them to becoming the first rap artists to ever get a sneaker deal, paving the way for future partnerships with rappers like Kanye West. At first glance, the trio’s style was indistinguishable, but DMC stood out as the most stylish member of the group, adding in a Kangol hat and thick-rimmed Cazal and Ultra Goliath sunglasses to his look. His style was more of a B-boy crossover, and that set him apart just enough.—Rob Marriott
Big Daddy Kane
Height of Style: “Smooth Operator” video
Signature Look: High-top fades, gold chains, velour suits, four-finger rings
Big Daddy Kane’s clean lines and the cameo with three cuts in his brow set the standard in the late ‘80s. Velour suits, four-finger rings, and the thick dookie chains—no one was doing it before him. Whether he was rocking T-Shirts by The Shirt Kings or pieces by Dapper Dan, he was hands down the most stylish member of the Juice Crew and defined the look of hip-hop’s golden era.—Rob Marriott
Height of Style: All Eyez on Me era
Signature Look: Versace leathers, gold jewelry, bandanas
2Pac remains the template for the fashionable gangster rapper. His overzealous tattoo game mixed in seamlessly with high-end touches from labels like Versace. His bandana tied into rabbit ears struck mythic chords and remains one of hip-hop’s most recognizable style flourishes to this day. A Dickies and Timbs man to the fullest, his dedication to workwear was unwavering. Remember when he rolled up to the Soul Train Awards in a “Thug Life” beanie, Carharrt chore jacket, baggy jeans, and wheat Timberlands? God Damn.—Rob Marriott
Wiz Khalifa
Height of Style: Rolling Papers Tour
Signature Look: Chuck Taylors, tank tops, unbuttoned shirts, and overalls.
Like Snoop Dogg before him, Wiz Khalifa’s style is typically covered by a cloud of weed smoke. Due to his ties to Taylor Allderdice High School in Pittsburgh—the same school that Mac Miller went to—Wiz has traditionally had an affinity for Chuck Taylors. For the most part, Wiz has always kept his looks super chill. Nowadays, you can catch him rocking unbuttoned shirts accompanied with a joint or a blunt. His unfussy approach to fashion has made him the spokesperson for the simple swag of the modern pothead.—Rob Marriott
Snoop Dogg
Height of Style: MTV Video Music Awards, 1996
Signature Looks: Dickies, Converse, button down, pimp suits
Snoop Dogg defined what a cool West Coast gangster was post-Eazy E—even more so than 2Pac at times. Staying true to his roots as a Crip, Snoop codified the cholo-inspired Dickies, Chucks, and button-up look when he first stepped onto the Los Angeles rap scene in the early ‘90s. Later on, he veered toward dressing like the illest pimp with coats that looked like they were stolen from the wardrobe of Super Fly. Although Snoop isn’t the most influential rapper when it comes to hip-hop fashion–let’s try to forget that strange Snoop Lion era—he certainly has impacted the game. From popularizing one of Tommy Hilfiger’s most iconic pieces on Saturday Night Live to having his face printed on one of Vetements most popular products nearly two decades later, Snoop deserves his flowers.—Rob Marriott
Height of Style: “Paid In Full” video
Signature Look: Dapper Dan Gucci suits and gold rope chains
Rakim’s trademark look of Dapper Dan Gucci jackets, heavy rope chains, rings, and his half-moon fade, defined drug dealer chic in the late ’80s. God’s menacing cool made this look iconic. The cover of Eric B. and Rakim’s 1989 album Follow The Leader, will forever go down as one of the hardest Dapper Dan fits of all time.—Rob Marriott
Height of Style: 2017 Met Gala
Signature Look: Bold prints and custom jewelry
From the moment they entered the scene with their breakout single “Versace,” the Migos have always been about fashion. Each member brings their own flavor, but as a unit, they thrive. The Georgia trio has a thing for jewelry, luxury brands, and memorable ad libs.—Maria Mora
Height of Style: DS2 era
Signature Look: Jeans, diamond jewelry, sunglasses, trophy jackets
Nayvadius hive, assemble. Future is no stranger to speaking about his obsession with luxury brands like Givenchy, Cartier, Margiela, and countless others—racking up hundreds of fashion references throughout his discography. The “Life is Good” rapper has mastered the art of personal style, one that makes you “tap for details.”—Maria Mora
Height of Style: 2018 “Stay Dangerous” era
Signature Look: Dickies uniform, tube socks, Chuck Taylors
If there was an image in the dictionary that depicts the LA uniform, YG would be standing right there. The Compton rapper pays homage to his city from head to toe—high tube socks, loafers, and tiny cat-eye glasses.—Maria Mora
Height of Style: Nike collaboration in 2017
Signature Look: Trainers, tracksuits, and Cuban links
There’s no question as to why Skepta is on this list. The grime artist from London marries tailoring with sportswear so well, leading him to land several Nike collaborations, a Uniqlo campaign, and the launch of his own label, MAINS.—Maria Mora
Height of Style: Front row at Chanel during Paris Fashion Week Spring/Summer 2020
Signature Look: Everything
Cardi B kills just about every category in fashion. Whether she’s going to fashion week, attending the Hustlers premiere, or hitting up an award show, the Bronx princess brings her fashion A-game every time with help from her stylist, Kollin Carter. Best of all? Her daughter Kulture is right there with her.—Maria Mora
Lauryn Hill
Height of Style: ‘90s
Signature Look: bright colors, statement accessories
Lauryn Hill released her critically acclaimed debut album, The Miseducation of Lauryn Hill over 20 years ago and her style still remains unforgettable. The Newark native stayed true to her fashion interests since day one with the Fugees—leaning on bold colors, statement earrings, and hair accessories as her go to look. Virgil Abloh recently tapped Hill to perform at his Spring/Summer 2021 show for Louis Vuitton.—Maria Mora
Height of Style: 2019 post “Drip Too Hard”
Signature Look: Rectangular shades, bold patterns, statement sneakers
He claims to have invented “drip” and we couldn’t agree more. Gunna is a walking fashion runway. While he does have a personal stylist of his own, Gunna often takes matters into his own hands and creates his own looks. When asked whether he knows something is working or not, Gunna told GQ, “You just gotta have the confidence to know it is. Everybody is not gonna like what I wear, but a majority of people are.”—Maria Mora
Height of Style: Takashi Murakami x J Balvin Collaboration
Signature Look: neon colored hair, Takashi Murakami jewelry, bright colors
Head of the Latino Gang, J Balvin isn’t afraid to step outside of the box with his fashion choices. The Colombian reggaeton artist loves bold colors; his 2020 album is aptly titled Colores. Whether it’s a lemon-colored suit at the Billboard Latin Music Awards or a pastel ensemble at the Louis Vuitton fashion show, Balvin’s bright personality is displayed very well on the red carpet.—Maria Mora
Height of Style: 2019 “Caro” music video
Signature Look: manicured hands, gender fluid style, rose tinted sunglasses
Known for shocking the Latin American audience with his painted nails, short shorts, and at times androgynous looks, Bad Bunny’s style is changing culture. He continuously defies stereotypes with his outfits, breaking those codes of masculinity that need to be challenged. What’s there not to love? —Maria Mora
Foxy Brown
Height of Style: Christian Dior’s muse under John Galliano
Signature Look: furs, glamorous
The self-professed “Dark-skinned Christian Dior poster girl” must be mentioned when discussing hip hop fashion in the 90s/early 2000s. Foxy Brown’s style went beyond the attention-seeking sexiness often used to command a room. She worked with Marvet Britto to work with brands like Christian Dior, and even had a fur collection with Alexis and Gianni.—Maria Mora
Beastie Boys
Height of Style: ’80s-’90s
Signature Look: clout goggles, Stüssy pullovers, blue jeans
Beastie Boys were truly ahead of their time. The NYC hip-hop trio were heavy into streetwear before streetwear was even a thing—rocking Stüssy hoodies, Carhartt jackets, clout goggles, and fresh pairs of Adidas. The enduring influence the Beastie Boys have on today’s subcultures and music scenes isn’t surprising at all.—Maria Mora
Kool Moe Dee
Height of Style: The Run-DMC freestyle battle with Special K on Graffiti Rock
Signature Look: Porsche sunglasses and berets.
Long before Killa Cam, one of Harlem’s finest was the one and only Kool Moe Dee. Who can ever forget that white leather jacket and beret he wore while staring dead into the camera during his freestyle battle with Run-DMC on Graffiti Rock? Kool Moe Dee was the flyest of the fly in the Treacherous Three. He’s also likely the first rapper to also violate another MC’s fashion choices—crushing LL Cool J’s red Kangol with a Jeep Wrangler for the cover of his album How Ya Like Me Now.—Lei Takanashi
Busta Rhymes
Height of Style: The Coming
Signature Look: Any and everything
Our first introduction to Busta was via Leaders of the New School and the “Scenario” video. We got a glimpse of his bombastic rhymes and style that only got bolder as his career progressed. When he wasn’t wearing candy-colored snorkels and applejack hats in the “Woo-Hah!! (Got You All In Check)” video, he was gracing red carpets in very daring looks, which included the teal linen jumpsuit he wore to the Source Awards in 2000 or the yellow leather halter-esque top he wore to the MTV Video Music Awards in 1999. As Busta’s gotten older, his style has become a little more subdued, but he took fashion risks that expanded the parameters of hip-hop style.—Aria Hughes
Grand Puba
Height of Style: “What’s the 411” on Yo! MTV Raps
Signature Look: Polo everything, Tommy Hilfiger shirts, Girbaud jeans, shades
Polo, Tommy Hilfiger, and Girbauds became standard issue in rap circles thanks to Puba constantly name-checking the labels. His crew, Brand Nubian, would become the cornerstone for a conscious-yet-cool movement that would influence fans like young Kanye West to make backpack rap.—Rob Marriott
Missy Elliott
Height of Style: Supa Dupa Fly and Under Construction
Signature Look: Custom matching sets, bold prints, unique headwear
Given Missy Elliott’s outsized imagination, which translates to her production, songwriting, and music videos, it makes sense that her style is just as interesting. She had a standout look from the jump: glossy black finger waves, beat face, custom leather jerseys made by 5001 Flavors, and baggy pants. Elliott entered an industry that expected female artists to be thin and one version of sexy, but she defied that with her bold looks and still achieved commercial success. Her 1997 debut album Supa Dupa Fly, and the string of Hype Williams-directed music videos that came with it, which June Ambrose styled, established Elliott as one of of hip-hop’s most theatrical, and quite frankly, iconic figures. Who can forget the vinyl bag she wore in “The Rain,” video? Or the red and white superhero space costume she wore in “Sock it to Me?” And the gold coat she wore in “Beep Me 911?” These looks are ingrained in our memories and influenced what many of us perceive as fly. She got a little more futuristic and intergalactic on Da Real World, which dropped in 1999 and spawned the “She’s a Bitch,” video. That’s another Williams and Ambrose production, which features fits that still look ahead of their time 20 years later. On the red carpet she was wearing heavily embellished custom leather sets in bright colors. With Under Construction, which released in 2002, she was all the way in her B-girl bag, sporting tracksuits from Chanel and Adidas—she signed a sneaker and apparel deal with the brand—and fuzzy Kangol hats. She also appeared in commercials for Gap, campaigns for MAC Viva Glam, and she partnered with Reebok in the early 2000s. Missy is truly one of a kind, and her style reflects that.—Aria Hughes
Salt-N-Pepa
Height of Style: “Ain’t Nuthin’ But A She Thing” video
Signature look: Sexy and coordinated
Salt-N-Pepa had an undeniable presence from the start. They came up right as it was becoming ok for female rappers to be a little more feminine, and they displayed that in the “Push It” video—the jackets they wore were made by Dapper Dan but designed by Christopher “Play” Martin from Kid N’ Play. From then on it was off to the races for the trio, who would eventually start to work with stylist Derek Khan. He would dress them in designers like Dolce & Gabbana, Versace, Thierry Mugler, and Van Cleef & Arpels. You can see how their style started to become more fashion in the Ellen Von Unwerth directed “Ain’t Nuthin’ But A She Thing” music video, that was styled by Khan and Patti Wilson. Salt-N-Pepa helped the industry see that you could be sexy and taken seriously.—Aria Hughes
Height of Style: Early 2000s
Signature Look: A mix of camp, high fashion, and hood
Does this entry need an explanation? Lil’ Kim, with help from stylist Misa Hylton, created a blueprint for how female entertainers and influencers dress today. Name it—wigs that match the outfit, designer logo wigs, nipple pasties, colorful furs—and she probably pioneered it, or at least popularized it. The internet is brimming with photos of Lil’ Kim, who clearly loves fashion, has no desire to look like anyone else, and has excellent taste. The lavender jumpsuit and matching wig she wore to the 1999 MTV VMAs is always top of mind, but how about the “No Matter What They Say,” video, which was basically a fashion editorial. Lil Kim mixed designer with “ghetto fabulous” staples that felt aspirational and familiar. Kim had a dream glam team, that included Hylton, Dionne Alexander on hair, and Nzingha Gumbs on makeup. As a celebrity it’s expected to have a glam squad. But to select the right people and push them into new boundaries that still influence people today, that’s VERY rare. She also helped hip-hop align with luxury brands. She was adored by Marc Jacobs, Alexander McQueen, Donatella Versace, and Karl Lagerfeld, and sat front row at shows in Paris before that was commonplace for Black artists. This led to deals with Candies, Mac, Old Navy, Iceberg, and more. Kim walked so everyone else could run.—Aria Hughes
Height of Style: Goodie Mob circa 1995
Signature Look: Afro, bucket hat, sunglasses, big smile
At Goodie Mobb’s peak, you could always rely on Big Gipp for a look. His style aligned with that of his Dungeon Family peers, but it also stood out. You first recognized him for his hair, which he either wore out in an afro or slicked up in a bush ball pony tail. But you couldn’t miss his sunglasses, which were always bright and came in off-kilter shapes. His outlandish but good outfits included baseball jerseys with madras pants, tailored, fur collared coats with knit beanies, and matching faux fur sets. It’s an idiosyncratic mix that’s become a signature for other popular Atlanta rappers including Andre 3000 and Young Thug. There’s definitely something in the water.—Aria Hughes
Height of Style: Present Day
Signature Look: Nike tracksuits, Air Maxes, Stone Island, Chrome Hearts denim, custom Brioni
Drake’s music career is nothing short of legendary. But while the awards and hit records have continued to pile up over the years, it has taken Drizzy a bit longer to find his footing in the fashion space. Needless to say, he’s finally found a lane that works for him. He has an affinity for Nike tracksuits paired with a fresh pair of Air Force 1s or Air Maxes. His latest video for “Laugh Now Cry Later,” which was shot at the Nike HQ in Beaverton and doubles as a giant Nike commercial, further cements his love for the Swoosh. He was instrumental in popularizing Stone Island stateside a couple years back as well. On the opposite side of the spectrum is Drake’s love for custom Brioni jackets and Tom Ford suiting when he feels like stepping out in $1 million ensembles. Speaking of expensive, his jewelry collection boasts pieces such as a one-of-one Jacob and Co. watch with a roulette wheel inside the face worth $620,000 or that Patek Philippe designed by Virgil Abloh that’s, “got his wrist going nuts.” These days, Drake’s uniform consists of Chrome Hearts denim adorned with leather crosses and those jackets with the buckles on them, “that Alyx shit.” We also can’t forget about his long standing OVO clothing line that has collaborated with the likes of Clarks, Takashi Murakami, and DSquared2 over the years. It’s time to give The Boy his flowers.—Mike DeStefano
Height Of Style: Belly
Signature Look: Wheat Timbs, baggy jeans, leather jacket, black skully
He’s had his unfortunate missteps; the Firm era Cowboy hat comes to mind. He has swung from the overwrought white mink of “Hate Me Now” video to the more subtle nostalgia of his Complex cover. He came early with the mafia suits and fake spectacles, but his most iconic look remains the Illmatic era leathers with his waves banging and a single gold chain. The pharaoh piece was remixed by Kanye some ten years later as a Ra falcon head and pyramid rings.—Rob Marriott
Height of Style: 2007 Ninth Annual “White Party”
Signature Look: White Suit
Sean Combs is one of the style gods of hip-hop, without question, and arguably the producer-rapper-mogul with the most fashion accomplishments to his name. His Sean John label was the first hip-hop line to get high-fashion props—a Council of Fashion Designers of America nomination for “Menswear Designer of the Year” in 2000—and his colognes are best sellers. He’s also known for his “white parties” where the Ciroc flows aplenty. Plus, if you look at Bad Boy as a whole, his style legacy lives beyond him. All of his artists were fly, which says a lot.—Rob Marriott
Height of Style: “Mr. Rager” video
Signature Look: Classic streetwear meets progressive fashion
Kid Cudi has the notion of the personal uniform down pat. Hardly ever seen without his Jordans (notable exception: that time he was spotted wearing Louboutin Rollerboy Spike Loafers), he usually pairs his covetable kicks with APC jeans and a variety of outerwear ranging from Louis Vuitton and BAPE to custom leathers he designed for Surface to Air. The mini-film “Mr. Rager” put his Surface to Air collaboration in the spotlight, showcasing the jackets in the context of an all-out gang war. He’s gone on to create other memorable collaborations, whether that was his red Giuseppe Zanotti sneaker with puffed up straps, or the Kids See Ghosts merch he worked on with Kanye West and Cynthia Lu of Cactus Plant Flea Market. And you can’t forget his APC collab or his multiple BAPE collections. What we’ve come to appreciate most about Cudi over the years is how discerning he is when it comes to working with other fashion brands. Everything makes sense and everything feels authentic.—Rob Marriott
