The Most Stylish Rappers of the '90s
These rappers set the bar for the '90s and brought us into Y2K with style.
Image via Complex Original
The '90s era of rap was filled with the birth of sheer thuggery. Guns, drugs, murder, explicit sex; and that's just on AmeriKKKa's Most Wanted. The introduction and subsequent emergence of "gangsta rap" could quite possibly be one of the biggest revolutions the music world has ever seen. Same goes for the blinged-out boasting that developed when rappers started making serious dough off their music. But one thing that was established that can be seen as an outright positive effect of the era was the style the rappers of this time period championed.
The whole "style is cyclical" argument is applicable to just about every period of fashion you can imagine. Except hip-hop style in the '90s. That's because it's never left. Pieces of it have existed ever since. All black outfits. Expensive shades. Big jewelry. Timbs, Wallabies or Jordans. And most of all, purveyed swag. We see them. We emulate them. Rappers were, and still are our culture's spokespeople. And these rappers were pioneers and catalysts. Pay homage to The Most Stylish Rappers of the '90s.
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Snoop Doggy Dogg
How he influenced style today: Having pride in repping your set can be translated into dope style.
It's been long known of Snoop's affiliation with a certain gang well-represented in the Long Beach and Compton areas. He repped them proudly in the '90s, but did it with so much flair and charisma, much like his rap-style. His laid back approach to his rhymes carried over perfectly into the way he rocked his casual flannels and sweatshirts with Chucks around the Dogg Pound. And when he decided to go full mafioso with the suited and booted look, Snoop's slender frame and Doberman-like facial features were almost invisible due to the light of his swag.
Master P
How he influenced style today: Six words: Hip-hop camo and custom jerseys.
Oh, you slept on Percy's style? The man who brought you one of the greatest rap labels to ever grace hip-hop? A label that brought us some of the most desirable custom basketball jerseys, like, ever? That was all Master P, dog. The mid-'90s was ruled by P's affinity for expensive glasses frames, camo and success.
Will Smith
How he influenced style today: You can have fun with what you wear.
Yes, we all wish we could forget the "Get Jiggy With It" and "Miami" catastrophes on Will Smith's rap resume, but there's no denying the rapper/actor's '90s style dominance. The youthful approach to Smith's outfits with bright-colored hats and shirts paired with some light denim or wild-ass Zubaz, finished off with a fresh pair of Nikes had everyone ready to to go the basketball courts to either ball out, chill with your homies, or holler at home honeys.
Puff Daddy
How he influenced style today: Monochrome looks weren't shit 'til Diddy did 'em.
It probably isn't hard to fathom that one of the most powerful black men in the world today, who built his empire from the ground up in hip-hop, is also someone who has an inkling of style. Puff Daddy and Biggie ran the early '90s in their Versace shades and silks and Puff continued his reign through the late '90s with Mase in their monochrome leathers and shiny suits. Didn't like it? You just a weak, jealous motherfucker.
Mike D
How he influenced style today: It doesn't matter what your race is when you have confidence to rock it like a G.
Mike D was a primetime trend-setter in the '90s. Not only was he a co-founder for one of the best streetwear brands to grace our shoulders in X-Large, but he was a catalyst in mixing traditional hip-hop wear of adidas tracksuits and big gold chains with street and skatewear, introducing it to a crowd that was mainly used to a particular look.
Rakim
How he influenced style today: High-end fashion could be made to look like it was from the streets, which was even cooler.
The rap squat on the cover of "Don't Sweat The Technique" with the denim parka and the high top Air Force 1s was very powerful. Rakim established his style in the '80s calling on Dapper Dan's high fashion-meets-drug dealer custom swag that carried over into the '90s with just as much fury. Regular cats ain't even know what MCM was until Rakim came through.
Eazy E
How he influenced style today: All black and a snapback? You can thank E.
Nobody—and we mean NOBODY—did laid back West Coast style from the streets like Eazy E. His uniform of a snapback and Jheri curl, black Coaches or varsity jacket and black Locs were unfathomably cool, thus becoming the uniform of about 90% of L.A. who ever listened to a rap record. He switched it up from time to time, throwing in some khaki Dickies or a denim jacket, but no matter what, he killed it. Eazy was cool as the other side of the pillow and we definitely have all been influenced by his contributions to hip-hop and the culture.
Raekwon
How he influenced style today: The most stylish drug dealer turned rapper that many have tried to emulate.
Not many rappers can say they turned one piece of clothing into a global fashion grail even 20 years after the fact. Raekwon's Polo Sport "Snow Beach" jacket appearance in the "Can It All Be So Simple?" video solidified him in the halls of hip-hop style. He could've lived off the strength of that, but Wu's style leader had the druglord chic look down for all of Shaolin and beyond to cling onto.
Ice Cube
How he influenced style today: You had to have a certain thugged out way of carrying yourself if you wanted to people to connect your look with your actual demeanor.
"OG" doesn't even begin to describe Ice Cube's laid back, Compton-inspired style of the '90s. A Jeri curl and a snapback were his signature items, usually paired with a dark crewneck, some black jeans and white sneakers; very simple, yet so powerful with hip-hop fans. While you can probably catch him getting played by a goddamn Coors Light can in some commercial today, his style in the '90s still holds clout today.
Ghostface Killah
How he influenced style today: Made it okay have lavish style and call yourself "pretty."
Gully. Lavish. Two completely juxtaposed concepts, but Ghostface Killah mixed them together with such perfection in the '90s. Hockey jerseys to keep it gully, but a silk bathrobe to encapsulate his lavish lifestyle. Then he'd throw on a big ass Cuban or his infamous Eagle bangle to set shit all the way the fuck off. And don't forget about the dip-dyed two-tone Wallabees. Nobody did Wallos like Pretty Tony.
André 3000
How he influenced style today: Showed that evolution can be drastic and awesome simultaneously.
Before he began wearing purple wigs and singing odes to women living in his lap, André 3000 established himself as an ATLien of style in the rap world. Even before he got into old Southern dandy style, never did he live by the style rules of hip-hop that most rappers tried to stick to in order to be safe.
Grand Puba
How he influenced style today: Polo and Tommy-esque looks are still going strong.
Puba's style influence is one of an unsung hero. If you were around in the '90s and wore Hilfiger, Polo, or Girbaud, you can pretty much thank the Brand Nubian rapper for that. He even garnered the attention of Tommy Hilfiger himself who was intrigued by how he re-interpreted his WASP-y brand into a street-certified favorite.
MCA
How he influenced style today: You can still be hip-hop with a little bit of punk or rock in you.
Historically speaking, the Beastie Boys are one of the most prolific music groups of any generation. Ever. Style-speaking, well, they own just as much prowess. Much of that praise is alloted to MCA's leather biker, hoodie, and ripped denim look that was equal parts rock 'n roll and hip-hop. And though we lost the great MCA almost two years ago to the date, his style influence is still prevalent amongst rappers and non-rappers today. Just think of the current style icons who are incorporating elements of punk and rock into hip-hop 'fits.
Notorious B.I.G.
How he influenced style today: Size doesn't matter if you carry yourself like a king.
Clocking in at 6'2, 395 lbs., Biggie Smalls' style was the illest. His affinity for Karl Kani was forever present, and he single-handedly made Coogi a household name in urban America. But there was something about B.I.G.'s swagger, even at his size, that was like a dark aura you could feel, but couldn't see. The King of New York ruled the rap game in the early '90s, but the strides he made in style for hip-hop fans was much larger than himself or what anyone probably could have imagined.
Tupac
How he's influenced style today: He made "fashion" okay for rappers to like.
Another icon taken from us too early, Tupac's legacy can not only be felt today through his resounding lyrics, but also from the timeless style. Tupac was basically the Kanye West of his time, setting off a whirlwind of "what's he wearing?" discussions whenever he made an appearance. Thugged out bandanas tied around his head paired with baggy overalls or a Red Wings jersey, or walking the runway in Milan for good friend Gianni Versace, Pac's style was and is undeniable and distinguishable from just about any other's to date.