The 35 Best Dressed New York Rappers of All Time

Prime Era: 2005-2009
Signature Look: A fresh perm, slim fit tee, B.B. Simon belt, and black shades
Ranking on Our Best NY Rappers of All Time List: N/A

Max B's "Boss Don Biggavell" aesthetic fused Harlem streetwear with luxury long before it became the norm. His Come Up DVD look in 2008—Bvlgari shades, a navy slim fit tee, a B.B. Simon belt, and his signature perm—is the blueprint. Perms were uncommon in New York, and Max's individuality, street credibility, and charisma made the look unmistakably his. His aura made everyday items like basic tees, white tank tops, fitteds, and Nike Goadomes feel like luxury items—even as he wore them with pieces from houses like Gucci, Louis Vuitton, and Prada. The Wave God’s wardrobe lives on today in the closets of this generation’s tastemakers, from ASAP Rocky to Bloody Osiris. —Izzy Izzo

Prime Era: Late 1997-2001
Signature Look: White tank top, baggy denim shorts, Timbs, and a choker chain
Ranking on Our Best NY Rappers of All Time List: 8

The year is 1997. Hip-hop is awash in glitz and glamour with shiny suits, Rollies, and Versace acting as the de facto uniform for the most popular rappers (not just the ones signed to Bad Boy). Everything is bright, colorful, and aspirational. And then, with the suddenness of a summer storm, a stickup kid from Yonkers named DMX changed the game. The music turned harder, more confrontational. But the look also shifted into something more grounded. A gruff everyman, DMX favored camo sets, baggy denim, and workwear. Shirts were optional. Bandanas and choker chains were his accessories of choice and he wore Timbs on his toes at all times. And when the clouds finally parted and the sun came out again, it became clear as day: Earl Simmons had molded hip-hop into his own image, both sonically and aesthetically. —Thomas Golianopoulos

Prime Era: 1991-1996
Signature Look: Afrocentric touches, colorful prints, denim shirts, layering, fun headwear
Ranking on Our Best NY Rappers of All Time List: 24

Tip has survived many fashion eras but his Tribe days are the ones we remember most fondly. Initially he was known for expressive prints and playful accessories; by the Low End Theory and Midnight Marauders years, it was a lot of denim and thoughtful layering. The common denominator throughout has been a resistance to trend-chasing and a bold freedom of expression that’s a natural extension of his music. Tip does a lot with his outfits without ever doing too much. —Donnie Kwak

Prime Era: 1987-1990
Signature Look: Door knocker earrings, gold ropes, custom jackets from Dapper Dan, black bodysuits
Ranking on Our Best NY Rappers of All Time List: N/A

After meeting at Queensborough College, Salt and Pepa worked at a Sears call center in New York alongside colleagues Martin Lawrence and Kid N Play. The aesthetic of hip-hop was just starting to get beamed out to the world, building toward its mainstream crossover moment, and the duo that gave us “Push It” in 1987 left their indelible mark, not despite of but because of their humble beginnings. They presented a version of women’s fashion (door knocker earrings, gold ropes, custom jackets from Dapper Dan, black bodysuits) that wasn’t about archival designer pieces or couture. Endlessly revisited, from the likes of Cardi B and more, the “Push It” video is a moodboard unto itself. —Ross Scarano

Prime Era: 2019-2020
Signature Look: Cartier shades, Amiri jeans, and Dior sneakers
Ranking on Our Best NY Rappers of All Time List: 27

While his time in the spotlight was tragically short, Pop Smoke left an era-defining imprint on New York City by pioneering the sound of Brooklyn drill and its look. The pieces were repurposed from across the country—skinny Amiri jeans borrowed from Los Angeles and Cartier Buffs from Detroit—and he turned them into the uniform for his music. His biggest hit, “Dior,” shared a name with the iconic French luxury house and made him an unofficial ambassador. His demeanor even piqued the interest of designers like Virgil Abloh and Rhuigi Villasenor, whose invitations prompted Pop’s first trip to Paris to experience fashion week. Growing up in the Flossy, Pop Smoke was always destined to be fly. His rapid rise and hit records just introduced it to a bigger stage than he could have ever imagined. He was on his way to becoming one of his generation’s biggest fashion icons. —Mike DeStefano

Prime Era: 1990-1994
Signature Look: Rocking a blue Seton Hall jersey in the “Check The Rhime” video
Ranking on Our Best NY Rappers of All Time List: N/A

Phife is the ultimate team player. During the early years of Tribe, he tried to blend in with the rest of the group, wearing the plaid, Afrocentric garbs associated with the Native Tongues.

Then the "Can I Kick It?" video comes out and here he is rocking a gorgeous Atlanta Braves jersey. In the early '90s, before jerseys took over, Phife was one of the main ambassadors, showing off his WFAN standom in various ways. Best part is he didn't discriminate with sports, pulling out well known looks, like the Devils hockey jersey in the "Oh My God" video, to the rarest, like somehow getting his hands on a Seton Hall jersey in the “Check The Rhime” video. It’s one of the earliest instances of a rapper wearing a basketball jersey in a music video. Right beside him was Q-Tip, rocking a Yankees gear with an Atlanta Braves hat. Suddenly, Phife's influence was spreading within his group. —Dimas Sanfiorenzo

Prime Era: 1983-1990
Signature Look: The uniform of the ‘80s street hustler
Ranking on Our Best NY Rappers of All Time List: N/A

From the Dapper Dan suits to the dookie gold ropes to the crispy Air Force 1s, hip-hop’s definitive looks from the late ‘80s were actually birthed by New York’s infamous street hustlers and then appropriated by the rappers in their orbit. LL Cool J has been very candid about this. Which is why the original A.Z., of Rich Porter and Alpo fame (whose collective drama was immortalized in Paid In Full), notches on this list despite a fairly obscure career behind the mic in the early ‘90s gangsta rap troop Mob Style. In fact, A.Z.’s influence was so strong that a few years later, Brooklyn MC and Nas affiliate AZ would assume his identity for his rap career (resulting in a $10 million lawsuit settled out of court in ‘95). Salute the genesis. —Noah Callahan-Bever

Prime Era: 2010-2015
Signature Look: Head-to-toe Barbie Pink
Ranking on Our Best NY Rappers of All Time List: 7

While Nicki Minaj wasn’t the first woman in rap from New York City to push boundaries in the fashion world (look up and down the list for some of predecessors), she was doing it at a time when no other woman was at the same level. She created the bluepinkprint for the generation that has come after her. Her style was eccentric, all-encompassing, and polarizing, from Harajuku-inspired looks at the VMAs to beautiful gowns at the Met Gala to official collaborations with Fendi. And we can’t forget about the signature accessories, like her bubblegum pink wigs or “Barbie” diamond chain. It’s normal to see women in rap align with major fashion houses today. We don’t get to that point without Nick’s legendary 2010s run. —Mike DeStefano

Prime Era: 2010s
Signature Look: Rick Owens, high-low mixes
Ranking on Our Best NY Rappers of All Time List: 18

Somewhere along his journey from Mos Def to Yasiin Bey, the Brooklyn rapper traded his underground rap uniform for an eclectic blend of streetwear pieces, religious garb, and high fashion—mostly Rick. "I like drawing connections between pieces and patterns that would make someone else think, ’Those two things would never go together,’” he told GQ. “Well, to me they do.” To us, too. —Donnie Kwak

Prime Era: 2010-2015
Signature Look: Vanson leather jackets, baggy denim, and diamond fronts
Ranking on Our Best NY Rappers of All Time List: N/A

Before the baggy style of ‘90s New York fully came back into the fold in the 2020s, Ferg, as a member of ASAP Mob, helped introduce it to a new generation. Throughout his career, he’s never been afraid to experiment with some more outlandish looks, including sequined purple tracksuits, à la Jonathan Davis, and baby-pink velour sets. But it always comes back to Harlem staples like a buttery Vanson leather, crispy denim, some clean white sneakers, and a Jacob and Co. Five Time Zone for good measure. God bless the Hood Pope. —Mike DeStefano

Prime Era: 1986-1989
Signature Look: Porsche x Carrera shades, leather sets, leather kufi hats, urban cowboy
Ranking on Our Best NY Rappers of All Time List: 39

Kool Moe Dee was truly an innovator. His early era with the Treacherous Three helped lay the framework for early rap music, and his battle in 1981 versus Busy Bee marked the birth of the lyrical MC. In the late '80s, he rode the wave of mainstream success, becoming the first rapper to perform at the Grammys. His look was that of Harlem opulence. By the end of the ‘80s, he departed from the b-boy style of his early career and donned leather looks: trench jackets, pants, and kufis. Gold chains and watches were always present. So were his pitch black Porsche x Carrera shades. It's important to always reflect on those who paved the groundwork and Kool Moe Dee is one of them. —Matt Welty

Prime Era: 1998-2003
Signature Look: Tom Ford-era Gucci, Galliano-era Christian Dior, mink coats, and designer bags
Ranking on Our Best NY Rappers of All Time List: 33

Foxy Brown is another one of the early trendsetters for women in hip-hop to really own her sexuality and personal style. She was the definition of luxury meets street. She rapped about designers the way male rappers spit bars about jewelry and cars, becoming a muse to designers like John Galliano and Calvin Klein in the process. She wore Tom Ford-era Gucci, Versace crystals, and her signature minks on red carpets. The "dark skinned, Christian Dior poster girl," proved luxury fashion and hip-hop weren't mutually exclusive. —Breeana Walker

Prime Era: 2000s
Signature Look: A fresh pair of rare Air Force 1s perfectly color coordinated with the rest of the fit
Ranking on Our Best NY Rappers of All Time List: 31

Fat Joe’s personal style has always been anchored in one fact: He’s New York City’s sneaker king. Watching the grainy footage of Joey Crack licking the bottom of his Air Jordans in 2004 is a rite of passage in the community. But Fat Joe deserves props for the outfits he built around his god-level sneaker collection. In the “Lean Back” days, that meant luscious fur minks and Terror Squad diamond chains. As he’s aged, he’s become the spokesperson for color coordination. While the strategy leads to some misses, there’s never been a doubt that Fat Joe has a commitment to getting fresh that refuses to fade with age. —Mike DeStefano

Prime Era: Late ‘90s
Signature Look: Head-to-toe Polo
Ranking on Our Best NY Rappers of All Time List: N/A

A ‘90s underground king with Fat Beats classics and collabs with the likes of Eminem, in ‘88 the Skillionaire co-founded the Crown Height racking crew that made Polo a staple of hip-hop fashion: the Lo Lifes. Whether he was dripped in the Snow Beach or classic ‘92 anorak, the Polo Rican’s reimagining of Ralph’s preppy designs as streetwear staples would forever change how rappers and rap fans dress. Indeed, thanks to Thirstin, bury we with the lo on. —Noah Callahan-Bever

Prime Era: 1986-1992
Signature Look: OG streetwear brands like Stüssy and Pervert, chill skatewear, and workwear
Ranking on Our Best NY Rappers of All Time List: N/A

Although they don’t usually get namechecked when people talk about stylish rappers these days, it’s inarguable that Beastie Boys have had some of the most enduring influence on fashion. Through their many eras—the punk rock “Cookie Puss” years, the cartoon-ish old school hip-hop fits of Licence to Ill, the garish ‘70s disco queen looks of Paul’s Boutique, the LA skater vibes of Check Your Head and Ill Communication, to even the retro-future uniforms of Hello Nasty—the Beasties have birthed style blueprints for multiple generations of downtown cool kids. Mike D was even a pioneer in streetwear entrepreneurship, bankrolling the brand X-Large. Walkin’ down the street with the fresh fly threads, 40 years later, Beastie Boys are still the biggest heads. —Noah Callahan-Bever

Prime Era: Late ‘80s
Signature Look: Gold ropes, Gucci sweatsuit, and part in hair on the Paid in Full album cover
Ranking on Our Best NY Rappers of All Time List: 4

Has anyone ever looked cooler than Rakim? In the 1980s, as hip-hop’s ethos crystallized, the microphone fiend reinvented rhyme schemes while rocking custom Dapper Dan Louis Vuitton and Gucci pieces—remixing luxury fashion with street aesthetics well before that became the norm. He sported chunky gold rope chains with oversized medallions and put a part in his hair, looks that defined the era. Rakim’s fashion contributions are well recognized; one of his Dapper Dan suits featured in the Smithsonian. His fashion peak may have been short lived but decades later, rappers and brands alike are still following the leader. —Insanul Ahmed

Prime Era: 2001-2009
Signature Look: The royal blue Los Angeles Lakers Mitchell & Ness jersey
Ranking on Our Best NY Rappers of All Time List: 43

Fabolous is likely the only rapper here who could also make a worst-dressed list. The last 15 years of fits have been…challenging—styled like a Jimmy Jazz mannequin, if Jimmy Jazz sold Bottega Veneta. But when he was starting out, he was one of the flyest. Check Sports’ intro to the world: in Lil' Mo's "Superwoman Pt. II" he pulls off three NFL looks despite only having two verses—a mint Seattle Seahawks 25th anniversary one, an Atlanta Falcons home edition, and a Tennessee Titans away jersey.

Fab was the best with throwbacks. He would become synonymous with Mitchell & Ness, pulling off bangers like the Dr. J Sixers jawn in the visuals for "Can't Deny It" and the iconic blue Kobe Lakers jersey in the "Trade It All Part 2" video. Even when the late 2000s came, and jerseys were going out of vogue, he was still getting his shit off; his Rich Young line had a nice little buzz in NYC, selling out in spots like Vinnie's Styles in Brooklyn or Sammy's in the Bronx. —Dimas Sanfiorenzo

Prime Era: 1993-2004
Signature Look: Custom Wallabees, a Versace plate
Ranking on Our Best NY Rappers of All Time List: 13

The fact was, Dennis Coles had warrants. Bounty hunters showed up to early Wu-Tang Clan shows looking for the man known as the Ghostface Killah, and so he covered his face on music video sets, during photoshoots, etc. For this gesture alone, his impact on self-presentation (and preservation) in hip-hop would go down in history (see: MF DOOM or Tony Yayo or billy woods, for distinct branches off this particular tree). Add his colossal jewelry, including the eagle bracelet (you’re already picturing it), his custom dyed Wallabees, his underrated bathrobe fits, and you have an idiosyncratic giant who bent more than just the English language to his will. —Ross Scarano

Prime Era: 1997-2001
Signature Look: Custom Indian kurtas at the VMAs and metallic bodysuits in the “What’s It Gonna Be?!” video
Ranking on Our Best NY Rappers of All Time List: 9

Through his work with director Hype Williams and stylists like June Ambrose, Busta Rhymes pushed ’90s hip-hop fashion out of its comfort zone with a barrage of eye-popping looks. He operated in a sartorial dimension all his own, wearing wild colors, shiny bubble coats, and dreadlocks under massive leather top hats while bugging out in front of a fisheye lens. He started designing his own clothing for events, and launched a brand called Bushi in 1999 that looked beyond the typical “urbanwear” fare of the era.

Throughout the decade, he made bold choices, like the time he rocked a sleeveless, red-and-gold Indian kurta to the MTV VMAs (his own design), or when he wore a metallic sci-fi bodysuit with Janet Jackson in the "What's It Gonna Be?!" music video. Whatever he wore, Busta gave us all permission to be fearless and outrageous. —Brendan Frederick

Prime Era: 1984-1988
Signature Look: Cazals, Adidas tracksuits, and shell toes
Ranking on Our Best NY Rappers of All Time List: 23 (Run only)

In the early ’80s, rappers dressed up when they got on stage, trying on everything from disco leisure suits to outrageous P-Funk costumes. When Run-DMC became the first rappers on MTV in 1984, they immediately stood out. Three stone-faced guys wearing all black: leather suits, turtlenecks, fedoras. Black Adidas tracksuits, black bomber jackets, and gold chains were in the mix too. At all times, they had laceless Adidas Superstars on feet—a fresh-out-the-box way to flex how new your sneakers were. The group’s influence was so undeniable by 1986, when "My Adidas" birthed the first major endorsement between a sportswear giant and a hip-hop act. When the group became hip-hop’s first crossover superstars, it represented a seismic shift in fashion, turning raw street style into hip-hop’s default sartorial approach for decades to come. —Brendan Frederick

Prime Era: 2019-Present
Signature Look: CDG button-downs, Louis Vuitton tailoring, and a wide assortment of rare archival fashion pieces
Ranking on Our Best NY Rappers of All Time List: N/A

ASAP Nast is a rapper by trade, but is best known for his style. The Harlem native mixes luxury brands with East Coast streetwear and silhouettes. He’s walked for Virgil Abloh in his iconic Spring/Summer 2019 Louis Vuitton menswear collection in Paris, modeled for major campaigns like Supreme x Yohji Yamamoto, and collaborated with brands like Comme de Garçons and Converse. Most often, he’s serving fashion inspo on his Instagram page, where he showcases his swaggy-yet-refined style. There aren’t many things that Nast can’t pull off. —Mariah Rivera

Prime Era: 1985-1995
Signature Look: A red Kangol hat, gold dookie chains, tracksuits, and Shirt Kings airbrushed pieces
Ranking on Our Best NY Rappers of All Time List: 5

The ladies loved Cool J, but the outfits that covered his ripped physique played a major role in making him a household name. He made the red Kangol legendary. He was one of the biggest stars instrumental in turning Dapper Dan and The Shirt Kings into era-defining designers. And just look at Tyler, the Creator’s ensemble of choice for his Don’t Tap The Glass era. That’s all LL. He’s also widely regarded as the rapper who started the trend of rolling up one pant leg. And who could forget his guerilla marketing for FUBU in that 1997 GAP ad? His contributions span decades. For the younger generation that simply knows him as “that guy from NCIS,” do your Googles. —Mike DeStefano

Prime Era: 2003-2009
Signature Look: The American flag fit from the “Dipset Anthem” video
Ranking on Our Best NY Rappers of All Time List: N/A

From Pelle Pelle jackets, to the iconic bandana crown, to redefining the rock-star aesthetic alongside Jim Jones and influencing Lil Wayne during the Can't Feel My Face era, Juelz Santana consistently shaped hip-hop style throughout the 2000s. He made pieces like True Religion denim and Prada America's Cup sneakers coveted by a generation of New Yorkers. Modeling in BAPE lookbooks and for Supreme photo tees alongside his fellow Diplomat Jim Jones only helped propel him further into the conversation. But arguably Juelz Santana’s crowning achievement in fashion is recontextualizing the stars and stripes. His patriotic outfit from the “Dipset Anthem” video is still referenced by streetwear brands like Supreme and reposted countless times over every July to this day. —Izzy Izzo

Prime Era: 1992-1997
Signature Look: Canary yellow Polo Snow Beach pullover from the “Can It Be All So Simple” video
Ranking on Our Best NY Rappers of All Time List: 26

Raekwon was just 23 years old when the Wu-Tang Clan exploded onto the scene during the summer of 1993. But from the start he came across as an old soul—and it wasn’t just because of the music. The Chef took fashion cues from the fly hustlers he grew up around, first in Brooklyn and later in Shaolin. Kangols. Gold fronts. Fat medallions. Leather coats. And Polo. A lot of Ralph Lauren. His pièce de résistance was a canary yellow Polo Snow Beach pullover that he rocked in the “Can It Be All So Simple" video. The look was so iconic that Ralph Lauren re-released the collection in 2018 for its 25-year anniversary. —Thomas Golianopoulos

Prime Era: 1987-1990
Signature Look: High-top fade, gold ropes, rimless glasses, a fly double-breasted suit
Ranking on Our Best NY Rappers of All Time List: 19

The smoother operator himself, Kane fused New York street style with the sort of suits—vines, if you’re hip—that would’ve warranted a paragraph in Iceberg Slim’s Pimp. In silk shirts, white double-breasted joints, bejeweled with four-finger rings and chains upon chains, Kane was suave. A playboy. The sartorial equivalent of what his voice did, running casual circles around the competition without a drop of sweat on his lapel. He once rapped about opening a school to educate MCs about mic skills, but it could’ve just as easily been a program for snappy dressing. Kane’s natural sex symbol status became too outré for hip-hop when he appeared in Madonna’s Sex—but from the perspective of 2026, getting photographed by the legend Steven Meisel with the queen of pop is nothing to be ashamed of. In fact, it’s pretty awesome. —Ross Scarano

Prime Era: Mid-’90s
Signature Look: Army jacket, bandana, Timbs
Ranking on Our Best NY Rappers of All Time List: 3

Nas got flashier the more successful he got—see his red-leather getup for the ’96 MTV VMAs and the infamous pink suit from the “Street Dreams” video—but we’ll always favor his embodiment of ’90s NYC utilitarian grit, from the era when a good Army/Navy store was better than Macy’s. Beanies, bandanas, tactical pants, Timbs, and army jackets (with linin’ to sneak a Uzi on the Island)—a perfect blend of function and form. —Donnie Kwak

Prime Era: 2018-2025
Signature Look: Archive fashion, rare designer bags, and avant-garde ball gowns
Ranking on Our Best NY Rappers of All Time List: 25

Despite a seven-year gap between her debut album and sophomore project, Cardi B transformed into one of hip-hop’s biggest superstars through other means, mainly her fashion sense. Whether she is making flash bulbs ring off upon arrival at the Met Gala, turning her court appearances into her own personal fashion shows, or showing up to Gillette Stadium in head-to-toe Bottega Veneta leather, there have been few artists as consistent as Cardi. And when she isn’t in flaunting one-of-ones ripped right off the runway of fashion’s biggest designers, she’s flexing her Birkin collection or nodding back to her upbringing in the Bronx with some Robin’s jeans and a Pelle Pelle. She’s already stamped as one of the flyest rappers that New York has ever seen. —Mike DeStefano

Prime Era: 2002-2006
Signature Look: The all pink fur with the matching pink Nextel walkie-talkie in hand
Ranking on Our Best NY Rappers of All Time List: 17

Similar to his rap style, it took years for Cam's swag to fully blossom. A chubby, Confessions of Fire–era Cam was rugged, rocking standard late '90s hood attire: tank tops, tees, and Avirex leathers. But then in the "My Hood" video—near the end of the SDE era—you saw a hint of what would come: Cam popped up in a Frank Lucas–inspired chinchilla fur.

That was the birth of the flamboyant Cam'ron. And by the time he re-emerged, this time in 2001 as a member of Roc-A-Fella, Killah Cam was Dandy Cam. There were more furs, but what really stood him out were the colors: the maroon Coogi hoodie in the "Oh Boy" video; the red, white, and blue Jeff Hamilton leather in the back of the Come Home With Me CD case; and of course the pink fur with matching Nextel at the Baby Phat 2003 fashion show. That last fit was the big bang moment for rappers rocking pink—a full year before Kanye would drop The College Dropout and try to take ownership of the trend. But really, with the exception of Barbie, no single entity has done more for the color pink than Cameron Giles. —Dimas Sanfiorenzo

Prime Era: 2003-2008
Signature Look: A backwards fitted, Ed Hardy tees, Chrome Hearts accessories, and B.B. Simon belts
Ranking on Our Best NY Rappers of All Time List: 45

Jim Jones’ contributions to New York style have aged well with time. That’s because the rock-star swag that he helped usher into hip-hop back in the 2000s with Ed Hardy tees, blingy B.B. Simon belts, and Chrome Hearts jewelry is more relevant than ever nearly two decades later. Capo was ahead of the curve. Couple that with his Supreme photo tee appearance and catwalk cameos for brands like Off-White and Kith. You have a resume worthy enough to crown him not just Dipset’s flyest member, but one of New York’s flyest ever. —Mike DeStefano

Prime Era: 1985-1995
Signature Look: Tommy Hilfiger, Polo Sport, and Girbaud jeans
Ranking on Our Best NY Rappers of All Time List: 44

A lack of mainstream success in comparison to his peers keeps Grand Puba from getting the level of recognition he should. Quiet as it’s kept, he’s a big reason why you correlate a lot of brands with ‘90s New York. Tommy Hilfiger and Marithé + François Girbaud’s places within hip-hop history, Puba deserves a lot of credit for that too. The Brand Nubian member stayed in, “Hilfiger on top, Girbaud on the bottom.” His habit of mixing colorful rugby sweaters, windbreakers, and ‘90s athletic sneakers came before it was common to see every rapper from the city doing it. His televised performance of “What’s the 411?” from 1992 is a particular highlight, which has turned the Polo Alpine rugby he rocked into a grail for Lo heads. When you heavily influenced Kanye West’s early backpack rap swag and have been cited by ASAP Rocky as one of best dressed rappers ever, you’re stamped as one of the best. —Mike DeStefano

Prime Era: 1993-1997
Signature Look: Colorful Coogi sweater, Versace shades, jeans, Timbs
Ranking on Our Best NY Rappers of All Time List: 2

The Notorious B.I.G. was one of rap’s great describers, and you don’t need more than his own lyrics to make the argument for his status as one of its great dressers, too. From sewing logos onto his shirts as a young student to graduating to Coogi, Gucci, and Versace—all black Timbs and hoodies, when the occasion called for it—he was sly and forward-thinking. With the craftsmanship of his jeweler Tito Caicedo, he popularized the Jesus piece, a feat that has few analogues. And he did it all while acknowledging that he was nobody’s idea of a model. —Ross Scarano

Prime Era: 1998-2004
Signature Look: Blue Yankee fitted, construction Timbs, Rocawear shirt, heavy denim, Rocafella chain
Ranking on Our Best NY Rappers of All Time List: 1

We see you rolling your eyes because of the button-up shirts in the club era. It might seem corny now but A) Clubs really were discriminating against Black and Brown patrons for dressing too “ghetto” at the time and B) It totally worked cause we were all dressing like that. The hello button-ups, goodbye jerseys moment is a reflection of Jay’s influence, but his three decades of flyness is unmatched.

Everyone has their favorite Jay era. From the drug dealer chic of his Iceberg Slim era—when he he wore durags to your so-called awards—to the cigar chomping, Armadale popping, Rocawear and a fitted era to his Maison Margiela with the snapback so you “see the cut through the hole” Watch The Throne era to the rap’s elder statesman era sporting tuxes and Basquiat hair alongside Beyoncé in Tiffanys ads. Jay has done it all. He had every accessory you could ask for; the cleanest Air Forces, the rarest art, the platinum when a lot of you thought it was white gold, and don’t even get us started on his watch collection.

He’s definitely the GOAT NYC rapper, but he’s arguably the most recognizable fashion icon too. —Insanul Ahmed

Prime Era: Early 2000s
Signature Look: Chanel’s finest
Ranking on Our Best NY Rappers of All Time List: 12

Provocative. Raw. Powerful. That's Lil Kim. A trailblazer in the truest sense of the word, she was the first female rapper to embrace her sex appeal and use it in a gritty, creative way, the first rapper ever invited to the Met Gala, one of the first to sit front row for (and even walk in) runway shows for some of fashion’s biggest brands, and even the only female rapper with her own photo on a Supreme tee.

From colored wigs sprayed with designer monograms to her iconic purple bodysuit and single pastie moment at the ‘99 VMAs, Kimberly Jones never flinched at pushing how women were "allowed" to present themselves. But she wasn't just about sex appeal. She put fits together effortlessly, from the Air Max 95 moment at the Junior M.A.F.I.A. shoot to head-to-toe Chanel to her more tailored court looks. Kim mastered her aesthetic and used every appearance to remind you exactly who she was. The poses. The hairstyles. The raunch. The Queen Bee’s raw, authentic approach laid the foundation for every female artist who came after her. —Breeana Walker

Prime Era: 1985-1990
Signature Look: An eye patch, Clarks Wallabees, and every gold chain imaginable
Ranking on Our Best NY Rappers of All Time List: 20

While The Ruler always made sure he was put together, whether that be in a finely tailored suit, a clean cardigan or your favorite luxury brand before most rappers were rocking it, the clothing was almost secondary for the legendary storytelling emcee. What Slick Rick is most known for is being the pioneer of flashy jewelry in hip-hop. He wore as many gold chains and medallions as he could fit around his neck, rings he could slide onto his fingers, and bracelets he could wrap around his wrists. He even iced out his eye patch from time to time. We don’t get bling without Uncle Ricky. —Mike DeStefano

Prime Era: 2011-Present
Signature Look: Raf Simons sweaters, Jeremy Scott x Adidas sneakers, Hood By Air tops, Black Scale hats, Rick Owens pants, Chanel sweaters, Bottega Veneta bags, Ray-Ban shades, custom jewelry by Alex Moss, etc.
Ranking on Our Best NY Rappers of All Time List: 40

With monikers like Pretty Flacko and The Fashion Killa, the bar is set very high. Yet, since stepping onto the scene in some Jeremy Scotts and a leopard Supreme towel back in 2011, ASAP Rocky keeps exceeding and upping his own standards. And he does it with relative ease. He’s one of those rare individuals that can pull off pretty much anything he puts on. Over the years, that’s included everything from reflective Dickies construction pants to leather Bottega Veneta sweatsuits. Along the way, he’s introduced an entire generation to designers like Raf Simons and Rick Owens, and cratered the popularity of brands like Hood By Air and Been Trill with that same influence. He’s, unfortunately, encouraged many stylish men to rock babushkas and turned striped Guess T-shirts into must-have items. He’s released sneaker collabs with Puma and shades with Ray-Ban. He’s presented runway shows for his clothing brand, AWGE, in Paris and New York. He’s the first person of color to be the face of a Dior campaign and is one of the few men to be a brand ambassador for Chanel. We’re talking about his fits again, but can you blame us? Fuck fly. He is fashion. —Mike DeStefano