15 Rappers Who Debuted With an Original Sense of Style

Image via Complex Original

Back when people thought pink polos would hurt the Roc, Kanye still didn't give a fuck. While the majority of the game was on jerseys, button-ups, and enormous tees, Yeezus set himself apart from the pack with a decidedly collegiate prep look. The bounty of bright Ralph Lauren polos, rugby gear, and backpacks, working in tandem with lyrics and content that were unlike what anybody else in the mainstream was spitting, immediately presented Ye as one of the most fearless and original rappers out sonically and aesthetic-wise, a mantle he still upholds to this day.

Your boy Rocky came out of nowhere as a Harlem cat with a mashed-up Houston sound, wearing a shirt that said "Fuck Swag" while his first breakout track, "Purple Swag," repeated "swag" over and over. In his next video for "Peso," he was draped up and dripped out in the upper Manhattan streets rocking peak No Limit era Master P spectacles, while name-dropping Raf Simmons and Rick Owens. That kind of brash culture class is what immediately set Rocky from the pack and diverted eyes to his debut. In an era when music videos no longer held as much significance as prior years, Flacko and his squad made visuals a centerpiece again. Needless to say A$AP Mob came on the scene bolder than most, wildly assured of themselves with the bars to back it up. Now that's how you put a crew on.

Trinidad James may be the butt of many a rap fan's joke, especially this week, but you can't say he didn't swagger onto the scene with a sum total of zero fucks to his name. The video for "All Gold Everything" practically appeared out of thin air, and if you weren't into the song (which, how could you not be?) then your attention was certainly captured by TJ's outlandish alphet. Dude looked like he dove headfirst into a few racks at his local thrift store, left wearing whatever clung to his body, and threw sixteen chains on for good measure. We're not saying it's something we would ever attempt, but for what it's worth, he pulled it off all the way to a [temporary] record deal.

The rap game's newest weirdo. Yes, that was a dress he wore during a video shoot. He doesn't care about admitting it and doesn't care if you care. He also isn't giving up his rare dress shop location because you're not allowed to get on his wave. That DGAF attitude is just one reason why Thugger has the game's attention in both his unique sound and very individual sense of style. As he gears up for his debut, his style is still evolving before our attentive eyes, and he'll undoubtedly continue to experiment with whatever sticks before he settles into an identifiable pattern. Or, he'll keep wearing whatever the fuck strikes him on that given day.

Danny's steez stands out starting with whatever wild style he's got his hair in, but aside from that he's much more of a silent assassin with the alphet even though his music and lifestyle might imply differently. His Detroit heritage definitely plays a part in his sartorial fearlessness, but instead of typical "player" fits he expertly tows the line between menswear and streetwear in a manner that gets respect on both sides, peaking with lookbook modeling and appearing in a Mark McNairy runway show. His knowledge of and history with fashion rivals that of his music expertise, and he's equally at home waxing poetic on Rockports as he is about Burberry. He even ventured into the clothing game himself, recently collaborating with Carhartt WIP and Dr. Romanelli on a capsule collection that definitely reflected his signature out-there look.

The "gentlemen" with attitude shook the game up with music that stemmed from  actual issues in their home turf, and they also put on heavy for their city, and by extension, their coast. The group stuck to a mostly black and rope chain fresh code, but most notably they repped hard with their hat game. Raiders and Kings snapbacks/fitteds are still staples in to this day, even on guys who have never even been to L.A. The hard look of the crew reflected their music, and it was an overall direction that resonated heavily with hip-hop, and can be seen still in the sound and look of the culture today.

The Fresh Prince is, from a style standpoint at least, the proto RiFF RAFF, with his affinity for bright colors and wild looks. But really, your favorite current stylish rapper would have to cite Smith as an influence just off of the way he rocked any piece, pulled off any combo, now matter how vibrant or loud. Even two decades later, none of his fits seem dated nor come off as fails. And on top of everything, the Air Jordan game was always flawless. Dude pretty much represented an entire era of style, but the most impressive aspect is that his manner of dress was dope from the jump.

There was no other name for RiFF RAFF's debut than NEON iCON, even if he didn't know it at first. A consistent clothing direction is one of the first things you notice about Jody Highroller upon introduction to him via one of his equally weird and entertaining music videos or YouTube day-in-the-life skits. It's immediately quite clear that this isn't a guy you'll ever see in gloomy, dark hues, let alone a street goth or all-black look. Jody is all presentation and theater and his varying vibrant looks, whether aquaberry or Versace rum punch (if that doesn't exist on his Instagram yet, it's just a matter of time), is one of his biggest props. It's wild and weird, but not only is he's been making it work since day one, and it's spreading amongst his fanbase. Don't sleep, because even if it makes you feel some type of way, RiFF may be a trendsetter on the low.

Pharrell may have transitioned between several stages of his personal style, but when he first captured the spotlight, he was fusing skate and hip-hop style in a way that was uniquely his own back then. And guess what? Before the Vivienne Westwood joint, P was known for his affinity for another type of hat. That's right, Pharrell came into the game sharing Ashton Kutcher's taste in trucker headgear. But beyond that, the super-producer pretty much put Bape and Japanese streetwear on the map by his own damn self, all the while exploring different areas of hip-hop style that most people were hesitant to dive into. Pharrell's abilities to blend various genres music is a near mirror of what he does with incorporating menswear, streetwear, and other subcultures into one cohesive look. All this has made him a modern day style icon.

While Rocky puts on for Harlem, Theo reps Brooklyn on a similar wave of mixing and matching luxury fashion brands to create his own eclectic style. When he first came on the scene he oscillated between suede blazers and fedoras, or leathers and formless snapbacks that would become the spine of his LVRS brand, flawlessly pulling off the menswear/streetwear blur with a dope pair of Js. There's a reason why dude has been sitting front-row at fashion shows around the world since day one, and why he's continuously cited as one of the best-dressed rappers in the game.

The Beastie Boys went through several style changes, always displaying a very fluid sensibility and thrift store-esque appropriation for everything from Doc Martens to ironic T-shirts and the occasional Santa hat. They brought a punk element to hip-hop that also took roots in classic streetwear. Throughout their insanely-long career, the Beastie Boys stayed in the arena of New York City steez, unique but not in a way that made them alien to the genre, a blueprint followed by numerous succeeding rappers.

Montana's been around for a minute, but when he finally broke through the mainstream a few years ago he was more than dressed for his welcome to the big leagues. You could tell Frenchie was all about the trap, not from his Cokeboys movement, but his blatant addiction to rare pelts—as well as Versace and Egyptian cotton (you know, the shit Jesus used to wear). The fuck-PETA takeover (he and Kanye are going to make great brothers-in-law) was cemented when he posted up on the XXL freshmen cover in one of the most legendary furs of all time. Your boy must really hate summertime weather.

After the rap game recovered from the shock and awe of Tyler's "Yonkers" video, The Creator's unique sense of style became readily apparent. Unique as per rap game standards, that is. His look is typical California skate rat but even as his star, acclaim, and cash flow ascended, his commitment to the steez never wavered in favor of typical rapper brands. He's still all about the jort cutoffs, tube socks, Vans, printed shirts, and yes, lots of vintage Supreme, to a point where he's basically marketed his uniform for the legion of Odd Future fans as Golf Wang gear. No one else could be menacing while wearing a printed cat T-shirt you'd expect to find at a bible belt gas station. 

Rap's most legendary storyteller has one of the most iconic accessories of all time, but his enduring image is deeper than the pirate patch. The Ruler regularly rocked more gold chains than you would've previously thought a human neck could sustain, and that's in addition to a ring on every finger and the most regal hat not owned by the Pope. With a uniform so defined by accessories, the actual clothes rarely mattered, but even so dude had the ill one-arm-outside-the-jacket sleeve-embodying-wealth look down pat as well. Your favorite rapper's jewelry game doesn't even come close—but damn if French Montana isn't trying to measure up.

The boys from Queens pretty much set the standard for the prototypical "rapper" uniform, and brought hip-hop music and hip-hop style to the masses. Rope chains, Kangols (dated now, but then, too flames) and either all adidas everything or leathered out. Throw in their penchant for large frames both shades and simple specs, and they've got one of the most instantly identifiable and enduring looks in music. Pioneers in music and fashion, Run, D.M.C., and Jam Master Jay hit the ground running with a sound and look that established a foundation for nearly every rapper out there to build upon.