Hip-hop style as evolved over the last 40 plus years, but one thing that’s remained the same is its influence. Here’s who we consider the most stylish rappers of all time.
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: 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
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
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
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 Evisudenim 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
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
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: 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
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
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: 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
For More Visit Complex: https://www.complex.com/style/2020/08/the-50-most-stylish-rappers-of-all-time