The Most Stylish Rapper Alive, Every Year Since 1979

Image via Complex Original

Most stylish moment: Being nicknamed Casanova Fly; living up to it

With any list of rappers, you can't go wrong by starting the conversation with Grandmaster Caz. He's already been widely hailed for killing countless park jams as the standout member of the legendary Cold Crush Brothers, and for ghostwriting Big Bank Hank's verses on the Sugar Hill Gang's "Rapper's Delight" that year. But he didn't earn the nickname Casanova Fly for no reason. He backed it up with a serious hat rotation, all-white suits, tight shiny leather zip-ups, and killer confidence to match.

Most stylish moment: Rocking "The Breaks" on Soul Train wearing a light gray suit-with no shirt underneath

When Kurtis Blow, the first rapper to sign a major-label deal, dropped his signature cut "The Breaks" and his self-titled debut on Mercury Records in 1980, he brought Uptown class to hip-hop. While rappers across the Harlem River were dressing in elaborate costumes, trying to compete with George Clinton, Blow kept it smooth, with patterned three-piece suits, butterfly collars and a sharply lined-up baby fro with the Jim Kelly sideburns.

Most stylish moment: Destroying Busy Bee onstage at Harlem World; looking fresh while doing it

In 1981, Kool Moe Dee was busy revolutionizing rap with his quick-tongued technique, releasing "Feel the Heartbeat" with the Treacherous Three. He stood out in that group not just for his pioneering fast rapping, though, which lay waste to Busy Bee at an onstage at Harlem World nightclub this same year-his sense of style outshined his bandmates as well. He hadn't yet made those imposing sunglasses his mainstay, but he was already killing it with the Kangols cocked to the side. Even creased Lee jeans made sense when Moe Dee wore them; it might have been the fresh-to-death MD nameplate belt, which seemed to say, "The doctor is in, ladies."

Most stylish moment: Taking fashion to Mars in the "Planet Rock" video

Yes, Afrika Bambaataa was way more DJ than rapper, but his style, particularly in this year's classic "Planet Rock" video, spoke loudly enough. Much like his musical innovations, Bam's fashion is a list of firsts: one of the first to re-popularize African leather medallions, and one of the first to rock a bro-hawk. (Fall back, Diddy.) When he wasn't onstage wearing Native American headdresses or P-Funk-inspired crowns, he was staying fresh in ripped denim vests and space-age wraparounds.

Most stylish moment: Pulling your dad's girl in the above outfit

One sign that hip-hop has changed: Back in 1983, one-third of one of the dopest groups around wore short shorts, a leather blazer with no shirt underneath and a big black "Zorro" style cowboy hat. On the mic with Whodini, who released their self-titled debut that year, Ecstasy played second fiddle to main vocalist Jalil Hutchins. But onstage and in their videos, it was his unlikely but striking trademark look that stole the show.

Most stylish moment: "Rock Box," the first rap video to get play on MTV

Run DMC's debut single, "Sucker MCs," didn't just turn hip-hop on its head musically. Much like hip-hop music, hip-hop fashion can be split into eras: before Run DMC, and after. Old-school rappers took sartorial cues from the disco era's excesses and Funkadelic's cosmic costumes. When Run DMC emerged, dressed like a mix between Shaft and guys you saw around your way-gold chains, black leather jackets, shelltoes (unlaced, naturally)-everything beforehand started looking silly. This is the hottest rapper, not rappers though: We had to give a slight nod to DMC for the unmistakable Cazal glasses.

Most stylish moment: Dominating "Soul Train" by performing "Rock the Bells" and "I Can't Live Without My Radio" in a white-and-Carolina-blue tracksuit and a bucket hat

Style is nothing without the proper swagger to accompany it. LL Cool J embodied this in 1985, when he burst onto the scene his classic debut, Radio. Like his mentors from the other side of Hollis, Run DMC, LL transformed popular street styles and made them into his own iconic uniform. But LL represented a distinctly younger, rowdier style (he was only 18 at the time, after all), with track suits, his signature Kangol bucket hat and four-finger rings, which would go on to become the rap fashion standard for much of the '80s. That is, when he was wearing clothes at all: Years before Tupac and his "Thug Life" stomach tat were your girl's wet dream, LL made shirtless the new shirt, becoming rap's first prominent sex symbol.

Most stylish moment: "Walk This Way," the first rap video to land in heavy rotation on MTV

Run DMC reasserted their sartorial dominance in 1986, partly from mere ubiquity: Their blockbuster album Raising Hell made them the first rap group to cross over to mainstream success. But there were subtle updates to their signature look: In the video for "Walk This Way," they rocked untied Adidas, and later lionized the shoe with "My Adidas, " which helped them land rap's first endorsement deal; meanwhile, in the video for "It's Tricky," they permanently entered the fur-hooded black parka into the streetwear Hall of Fame. Sorry, Run: DMC upped the ante on you yet again by tinting out his signature specs.

Most stylish moment: Looking like money on the cover of Paid in Full

In 1987, just a few years after crack began flooding U.S. streets with dirty money, Rakim perfectly captured the hood-rich look of the time. The cover of his classic 1987 debut with Eric B, Paid in Full, features one of the iconic, unforgettable clothing items of all time: matching, custom-made Gucci leather coats from legendary Harlem clothier Dapper Dan, who chopped up designer items into his own imaginitive creations. In the video for "I Ain't No Joke," Rakim is the last person to successfully pull off mutton-chops.

Most stylish moment: Wearing an ankle-length mink in the "Teenage Love" video

In 1988, when Slick Rick hit his peak with his debut album, The Adventures of Slick Rick, he took hip-hop fashion to opposite extremes, making it both classier and gaudier than ever before. The street-inspired styles of the prior years were cleaned up on Rick, with smooth but colorful suits, topped by a Kangol newsboy cap to the side (the English accent didn't hurt, of course). At the same time, he went in the other direction, by wearing more gold than anyone's ever worn before or since. And of course, no one's ever rocked an eye patch that well.

Most stylish moment: Melting hearts in the "Bonita Applebum" video

The Jungle Brothers and De La Soul helped introduce the bohemian, Afrocentric look to a rap world still dominated by LL Cool J's macho B-boy look (see De La's "Me Myself and I" video), but Q-Tip is the one who showed that it could be smooth, fashionable and, let the ladies tell it, even sexy. In 1990, when he and A Tribe Called Quest unveiled their debut, People's Instinctive Travels and the Paths of Rhythm, he pulled off tie-dye and baggy Kente-patterned pants, but he also cleaned up well too, rocking a button-down and khakis with casual nonchalance in the video for "Can I Kick It?"

Most stylish moment: Rocking a flat-top with zig-zag styling in the "Smooth Operator" video

Big Daddy Kane may only reign for one year of this list, but that's only because of the thick competition (Slick Rick and Rakim, namely). Either way, in 1989—when he solidified his legacy by dropping second album It's a Big Daddy Thing, his highest-selling—you couldn't tell him anything. He made rap fashion grown-er and sexier than ever before, with an undeniable pimp influence: colorful silk shirts, velour, baggy off-white suits, a gold-tipped cane just 'cause. To top it all off, he's arguably the owner of the best flat-top of all time, whether a straight-up box or more embellished styles and shaved-in shapes.

Most stylish moment: Channeling Al Capone in the video for "Appetite for Destruction"

Like a hip-hop Karl Lagerfeld, Eazy E rocked a fashion uniform, an unchanging daily look that eventually became like his own iconic, unmistakable symbol. The most important parts were the tasteful Jheri curl, the black Raiders cap, the impenetrable Locs, and the unshakeably stoic demeanor, which he'd already established in the late '80s. But in 1991, when NWA released the incredible Niggaz4Life before splitting bitterly, Eazy also helped popularize the denim Carhartt jackets and Dickie short-sleeves (formerly mainly rocked by construction workers) that became ubiquitous in the early '90s.

Most stylish moment: Signing an endorsement deal with Tommy Hilfiger before you even knew who that was

While most other rappers were experimenting with making super-casual practical gear—sportswear (Starter, Columbia) workwear (Carhartt, Dickies) and fatigues—fashionable, Puba went in the other direction, taking his fashion cues from Ivy League preps and New York's legendary Lo-Life crew. But rather than only rocking the man on the horse, when Puba went solo with 1992's Reel to Reel, he wore extra-large pieces from another colorful, preppy American line, Tommy Hilfiger. Around the same time, a chance meeting between the designer and Puba led to an endorsement deal, which helped make Hilfiger a hip-hop go-to throughout the '90s. On top of that, Puba single-handedly blew up Girbaud jeans, and helped make backpack a fashion item.

Most stylish moment: Too cool for school Check Your Head album cover

If you read our piece on the Style Evolution of the Beastie Boys, you already know: Mike D was quietly killing them around 1993. Musically, the Beasties were everywhere, having just released their landmark Check Your Head and prepping Ill Communication for the year after. In terms of fashion, though, their influence, particularly that of Mike D, was perhaps as profound.

In 1991, Mike D helped co-found the pioneering streetwear brand L.A. X-Large, and two years later it was hitting its peak. At the brand's stores, and in the Beasties' iconic videos at the time, Mike was helping to spark trends that still live on today. At a time when the latest Jordans, Pumps and Air Maxes were all the rage, he was rocking vintage Pumas and Adidas (X-Large stores sold rare kicks as well). He and the Beasties took skater and cholo styles from L.A., where they lived at the time-baggy khakis, plaid shirts, skullies-and melded them with their New York hip-hop aesthetic, a then unheard-of culture clash that still informs streetwear to this day.

Most stylish moment: Giving Diddy the idea for white parties in the video for "Juicy"

The seed for the oncoming shiny-suit era was planted in 1994, when Biggie’s Ready to Die hit the streets. Perhaps in a reaction to the still-raging crack epidemic,  rappers were dressing like soldiers (Timbs and camo) on the East Coast, and like gang-bangers (chinos, bandanas, plaid shirts) on the West. Biggie’s signature Coogi sweaters and Gucci shades made it OK to floss again—even if some took it too far later on.

Most stylish moment: Graduating from that same damn 'Lo sweater in the video for "Heaven or Hell"

Though some of his Wu-Tang brethren were still wearing fatigues and hoodies, Raekwon was always into finer things. In a throwback to the Paid in Full/Dapper Dan era, Rae rocked "witty unpredictable fly shit" when it came to his wardrobe: colorful, patterned shirts of preumably Italian origin, gold fronts, two-tone butter leathers, a tight fade with a freshly cut half-moon part and thick gold chains-hence the title of Only Built 4 Cuban Linx..., which dropped this year.

Most stylish moment: Chilling with porn stars in the video for "How Do You Want It"

It may be hard for some to see the style in a bandana, baldie, tanktop, tattoos, baggy jeans and Timbs, but the fact that Tupac pulled that off, and somehow made it look good, speaks to his irrepressible charisma. After his death this year, millions of thugs both real and imagined across the world began dressing the same way. On the other hand, he rocked a three-piece suit better than almost anyone-see the classic videos for "2 of Amerikaz most Wanted" and "I Ain't Mad at Cha."

Most stylish moment: Rocking Versace on a boat in the video for "Hypnotize"

Biggie was murdered on March 9, just days before his double-album magnum opus Life After Death hit stores, but his impact on our ears and eyes would live on throughout the year and beyond. Matching his grander, expanded musical vision, he classed it up even further with his wardrobe during the album run-up. The colorful Coogi sweaters and Versace shirts were replaced with monochrome black or white ensembles of three-piece suits and a simple derby; he successfully both preceded and avoided Diddy's shiny suit craze, which was literally just weeks around the corner. A cane-which, surprise, he actually needed due to a car accident-completed the look.

Most stylish moment: His all-tan ensemble in the video for "What You Want"

Even in death, Biggie ruled 1997, but the next year Mase finally hit his own stride. At the end of the year prior, he dropped his chart-topping debut, Harlem World and the hit singles from the album stretched well into 1998. Puffy (or maybe his stylist) is probably the brains behind the so-called "shiny suits" that ruled in videos like "Mo Money Mo Problems," but Mase is the only person whoever really rocked the look well, supplementing it with his own Harlem touches: white-on-white Air Force 1s, a backwards fitted, a Jesus piece, and that undeniable swagger. Mase's Children of the Corn crewmate Cam'ron would revive the look years later, swapping the shiny tin-foil fabrics for bright pink animal skins.

Most stylish moment: Anytime he was seen with J. Lo

Bad Boy went for the threepeat in 1999, when Diddy emerged as a superstar in his own right with his official solo debut Forever (1997's No Way Out was billed to "Puff Daddy & the Family"). For the first time, after a decade-plus ruled by casual streetwear, Diddy made it OK for rappers to wear high-end suits half the time. He cashed in on his growing status as a style icon by launching Sean John the year prior; it eventually became one of the most profitable, respected urban fashion lines of all time. To top it all off, back then he was sporting the flyest accessory of all: J. Lo on his arm.

Most stylish moment: Wearing a custom Gucci jumpsuit while eating waffles in the "Cherchez La Ghost" video

In 1993, when Wu-Tang debuted, Ghostface hid his grill behind scarves, skullies and wraps. In 1995, he was dying his Clarks Wallabees "blue and cream." But by 2000, he and his fashion had evolved even further, to near Liberace levels. When his sophomore album Supreme Clientele dropped that year, he was rocking luxurious bathrobes as outerwear and somehow making it work. But his real coup was the most imaginitive rapper jewelry of all time: a huge solid-gold eagle perched on an armband.

Most stylish moment: His brown-and-orange Cleveland Browns–inspired get-up in the video "Young'n Holla Back"

Never underestimate the power of meticulous color-matching. Or at least not if Fabolous is doing the matching. When he released his 2001 debut, Ghetto Fabulous, Fab perfected the flawlessly color-coordinated combination of throwback jersey (whether baseball, football or basketball), fitted hat over a do-rag, and Air Forces. It's game time.

Most stylish moment: Channeling "Harlem Nights" in the video for Busta Rhyme's "Pass the Courvoisier Pt. II"

2002 is the year that Pharrell Williams, one of the true style icons of the new millennium, rapper or not, emerged as a fashion force in his own right. Musically, he and Neptunes partner Chad Hugo were already in the middle of an amazing run of producing blockbusters, which often spotlighted Pharrell's rapping or falsetto singing on the hook and featured him in the accompanying video. They won Producers of the Year at the Billboard Awards, and released N.E.R.D.'s first album the year before. But sartorially, P was beginning to shine as well, with a style that was more skate than street: his mainstay yellow N.E.R.D. mesh trucker hat (well before hipsters got a hold of them), a logo T, and skinny jeans (skinny by 2002 standards at least).

Most stylish moment: Wearing rainbow plaid to the Billboard Awards

In 2003, with Outkast making the rounds to soak up the accolades for that year's double-album banger Speakerboxxx/Love Below, Andre lit up with the dandy look he was pioneering on red carpets worldwide. It's become an increasingly popular style since, but Dre was one of the first to bring it to a hip-hop context, with tight three-piece suits, knickers, ties and bow ties, and tons of classic British patterns, from plaid to tweed to houndstooth.

Most stylish moment: Cruising through Harlem in a pink Range Rover in the video for "Killa Cam"

Around the time his classic Purple Haze dropped in 2004, Cam'ron took Harlem's infamously flamboyant swag to gaudy heights not seen since crack kingpins like Alpo ruled the streets in the late '80s: Huge yellow-diamond earrings normally worn by rich grandmothers—"I call 'em Lemonheads," he raps on "Killa Cam"—fitteds and do-rags, and, of course, all pink everything: leathers, minks and even his Range Rover.

Most stylish moment: Flossing with a croc-skin duffle bag on the album booklet for Late Registration

2005 was a big leap forward for Kanye. In February, he and his 2004 debut The College Dropout dominated the Grammys with 10 nominations, three wins and an unforgettable acceptance speech. In August he released his classic Late Registration and made headlines for his "George Bush doesn't care about Black people" moment. His wardobe reflected the growth: Half the time, he still rocked the preppy, Polo-heavy backpacker look, like Grand Puba reincarnated; the other half, he was starting to rock the high-fashion blazers and suits he's often seen in nowadays. Either look could've topped the list by itself.

Most stylish moment: Rocking a Maharishi hoodie in a GQ article naming him one of the Breakout Men of the Year

With Lupe's "Kick and Push" popularizing skateboarding in hip hop like never before, it only made sense that he was also killing it with streetwear, which was then arguably at its peak. Back in 2006, that meant all-over print hoodies, lots of Bathing Ape, and SB Dunks (naturally), all given a professorial slant with Lupe's trademark oval glasses.

Most stylish moment: Opening Billionaire Boys Club / Ice Cream Clothing's flagship store in SoHo

Pharrell killed it all millennium, but he truly domineered the spotlight again in 2007 with In My Mind, his solo debut. It's no exaggeration to say that he was the crown prince of streetwear, rocking his own Ice Cream and BBC brands most of the time, and making the baseball cap pulled low, T-shirt, hoody and jeans his go-to uniform. But he was cleaning up with best of them, whether pinstriped three-piece suits or going with a Miami Vice khakis and unbuttoned silk shirt look in the video for "Number One."

Most stylish moment: Donning a glow-in-the-dark vest and sunglasses while performing at the Grammys

Kanye jumped out to the top of the pack once again when he stepped up his closet with the release of 808s and Heartbreak, and more to the point, the debut of his own clothing line early the following year. He spent much of his time hobnobbing at European runway shows and fashion houses, and teamed up with Louis Vuitton for a line of shoes. One go-to look was a Pee Wee Herman-inspired suit, retro circular glasses and a white button-up rocked sans tie. He also announced the launch of his much-hyped would-be clothing line, Pastelle, which he folded in 2009.

Most stylish moment: Suiting up for GQ's Gentlemen's Ball

Like his then GOOD Music boss Kanye, Cudi, who unveiled his debut this year, found his style sweet spot by mixing traditional streetwear with high-end European brands and a healthy splash of rock 'n' roll. Nine times out of ten for Cudi that meant a Balmain jacket, a vintage T-shirt or Bathing Ape top, lived-in jeans and Jordans.

Most stylish moment: Wearing technicolor red from head to toe in a comeback performance of "Runaway" at the VMAs

After banishing himself to Hawaii after Taylorgate, Kanye reemerged in 2010 with an amazing new album, My Beautiful Dark Twisted Fantasy, and even more honed eye for visuals and fashion. Spending more and more time in Paris and Milan, Kanye was usually seen in all black Margiela, Balenciaga or Givenchy, though he didn't drop his earlier Prada fetish. He also began his obsession with leather bottoms (pants for now-the kilts came later), often off-set by bright white kicks.

Most stylish moment: Performing at the Victoria's Secret fashion show in all black with Kanye

Jay-Z has popularized so many street fashion fads over the years: platinum jewelry, throwbacks, button-ups, Yankee hats. He wasn't always the most stylish, but there's no doubt he had a talent for trendsetting. In 2011, he finally tops this list, partly by fancying up in a whole lot of perfectly cut, Rat Pack-inspired suits. But he was also outdoubtedly inspired by Kanye, who he collaborated with on Watch the Throne this year: On their blockbuster joint tour, Jay wore all-black, a lot of leather and mutiple gold chains, dressing every bit as fly as Yeezy (or maybe even flyer, if you aren't into kilts). He toned it down compared to Kanye of course, though he get everyone talking when he pinned an ornate Dries Van Noten man brooch on T-shirts and jackets.

Most stylish moment: Rocking red bottoms in Paris in the "Goldie" video

Harlem caps its domination of this list with the emergence of ASAP Rocky. Like his music, Rocky's style took inspiration from disparate, seemingly disconnected sources: '80s NYC drug dealers, '90s West Coast gang-bangers, new-millennium streetwear (his manager, Chase Infinite, is manager of noted brand/store Prohibit NYC, where ASAP was a frequent customer), and cutting edge European high fashion. It all comes together in the 2012 video for "Goldie," which features him driving around Paris in a mink wrap, a knee-length parka, Louboutin loafers and his everyday braids, gold fronts and snap-back.

Most stylish moment: Hitting the Louis Vuitton show at Men's Fashion Week in Paris wearing a fur-lined Ermanno Scervino parka

2013 was business as usual: Kanye forcing other rappers to max out their black cards to keep up. His obsession with black, leather and left-field European fashion houses continued-and maybe even intensified as he holed up in Paris to complete Yeezus. On his feet, Japanese brand VISVIM or his own all-red Yeezy 2s were mainstays. However, his sentiment this year is probably best summarized by the red ski mask he's been seen in (and by the music on Yeezus, for that matter): He doesn't give a fuck.