From the very beginning of its history, Hip-Hop has been inextricably connected to and influenced by the culture of the street. So much of the subject matter, cultural voice, and perspective that informs so much of the art comes directly from the communities that birthed it. Crime was ever-present, even as the culture sought to elevate above it: MC’s took names that reflected the drug hustle going on around them, early DJ’s played the parks where stabbings and muggings took place regularly. And the kingpins influenced a culture of cool that young people from around the way would emulate.

Hip-Hop style and fashion has been inarguably informed by the neighborhood hustler, and while those looks now occupy some of the glitziest runways around the world—it’s born of a world far removed from the glamour of those platforms, but nonetheless one of prestige. In the late 1970s and early 1980s, as rappers made the leap from block parties to recording artists, many acts believed they had to dress the way punk rock and funk stars dressed on television. The early photoshoots for artists like Grandmaster Flash and The Furious Five and others reveal how closely the look traced what was already established for “stars” of the time. But it was a trio from Queens who showed up later that reconnected mainstream stardom to the street looks that gave Hip-Hop it’s soul.

Run-D.M.C.’s trademark look—black fedoras, laceless adidas sneakers, and leather—was born of their DJ, the late Jam-Master Jay, who was connected to Queens street hustler culture. When he was asked to join Run and DMC in their group, they had no look of their own. Group manager Russell Simmons told the pair they should emulate their turntablist. Jay forever connected Run-D.M.C.’s visual to the streets that he’d known so well.

“He had a tremendous sense of B-boy style,” Run-D.M.C. biographer Bill Adler said of Jay’s style back in 2002, shortly after his murder. “He was wearing a version of their classic all-black look two or three years before there was a Run-DMC.”

“Jay was cool enough to know everything that’s cool,” Run explained last year.  “The leather suit—Jay. Cazale [sunglasses] with the eye lenses popped out—Jay. This hat—Jay. We wore the hat because Jay set the tone. The adidas with no shoe strings [was] Hollis. Street culture, Jam Master Jay--fashion.”

Longtime Jay associate Rodney “Boe Scaggs” Jones talked to AllHipHop.com about Jay’s street ties—while dismissing any notion that the legendary deejay was involved in any hustling himself.

“Jay wasn't into that,” Scaggs told “Grouchy” Greg Watkins in 2011. “He wasn't into dealing with drugs or no shit like that. I mean, I heard people say things like that, like I hear the streets talking. He wasn't into hustling drugs and all that. He was too busy making his own career and making a career for his nephew and trying to make sure his sons is cool. His brothers and sisters were straight. He wasn't worried about moving no drugs.”

 “He's from the street. Just because you know a certain type of people don't mean you're involved with the same thing they involved with.”

Photo by Noam Galai/Getty Images

Hip-hop stars and their connections to the streets led to the style and trends of the streets suddenly flooding mainstream America via rappers. For most of the 1980s, the image of the Black mainstream was tied to Huxtable-esque respectability. But as Hip-Hop emerged, the look and style of the neighborhood became much more visible. And no one was more responsible—and no one did more to bridge the streets and the stars’ style--than Harlem’s legendary haberdasher Dapper Dan.

Dan, born Daniel Day, opened his boutique on 125th street in 1982. He’d grown up poor in East Harlem, but was committed to dressing in a way that conveyed distinction. He started in fashion as a mostly self-taught furrier, before opening his shop between Madison and Fifth, and outfitting some of the most notorious drug dealers in New York City.

Harlem drug dealer Alberto “Alpo” Martinez was one of Dan’s most famous customers. Alpo rocked a tan-and-brown snorkel parka with a fox-fur hood and Louis Vuitton logo-print—it became known as the “Alpo Coat” and became a standard-bearer for hood fabulous chic in the 1980s. “They were my primary clientele, the look spread outside the hustler culture and was embraced by the whole rap world, and they just took it everywhere,” Dapper Dan told Dazed in 2014.

“So goes Harlem, so goes the Black world,” he explained to Life + Times. “So the rappers want to be like the gangsters.” Once teenage hip-hop star LL COOL J walked through his shop’s doors in 1985, Dapper Dan became the go-to name for rappers and recording artists. Artists from Salt-N-Pepa to Bobby Brown showed up at Dapper Dan’s over the next several years—and Eric B. & Rakim famously rocked his iconic jackets on the cover of their landmark 1987 classic Paid In Full.

Photo by Christie Goodwin/Getty Images

“My father taught himself how to read,” Dapper Dan relayed to LL COOL J last year. “Everything started coming to me later on in life, and I said you know what my father taught himself how to read. Imma teach myself anything I want to know. I’m gonna study textile printing and figure out how to turn them symbols on that bag into garments. So I taught myself independently, all by myself, everything that I need to know about textile printing. Once I came up with it—bam!—LL was parked outside!”

A 1988 visit from heavyweight champion Mike Tyson—a night that famously ended in the champ brawling with Mitch Green—resulted in more scrutiny on Dapper Dan, and copyright lawsuits ensued. His shop was subsequently shut down in 1992.

Kingpin culture was influencing looks and status within Hip-Hop. Legendary hustlers shaped how rappers wanted to be seen. Slick Rick’s ostentatious chains were directly influenced by NYC drug lords. Supreme Magnetic and the original 50 Cent appeared on the back cover for Eric B & Rakim’s Paid In Full.

In Chicago, the infamous Larry Hoover of the Gangster’s Disciples launched his own Ghetto Prisoner Clothing in the mid-1990s. "All kids in the ghetto can associate with the idea of prisoners and being treated like prisoners," Hoover said about the line in 1995. Hoover’s company was raided later that year. Atlanta’s B.M.F. (Black Mafia Family) became known for its opulence as much as its notoriety as a drug trafficking operation. Big Meech’s penchant for gaudy flash became a benchmark for a cadre of southern rappers—including associates like Jeezy and Rick Ross. Meech even appeared as himself in a rap video—while he and his company were under investigation. Meech’s reputation led to him being name-dropped in songs from Ross’s “B.M.F.” to “Hustlin’.”  And it’s been claimed that “making it rain” was invented by Meech, and as southern hip-hop took over the mainstream, Meech’s look—expensive shades and furs, along with lots and lots of cars—informed virtually every rap video being made in the early 00s.

As NOLA Hip-Hop took over the airwaves in the late 1990s via labels like No Limit and Cash Money Records, the voice of the project dope boy championed the merits of the classic Reebok Workout. Cash Money rappers like Juvenile and Lil Wayne made the shoe part of their cultural trademark—a reflection of the street hustlers’ look that had dominated New Orleans throughout the 1990s. The shoe was so connected to the streets, it was nicknamed “The Soldier” by locals.

“In New Orleans in particular, the Soldier was the uniform, if you will. People wore it as their uniform and as their street gear,” Reebok Classic's Global Product Manager James Hardaway shared in 2018.  “Certain musical artists used to sing about it in their songs and talk about how they wear their Reeboks or their soldiers. It really became a cultural phenomenon there.”

This wasn’t exactly flashing on the level of local kingpins, it was more the style of corner boys making its way into the mainstream. As Cash Money videos presented the rappers in baggy white tees, durags and those ever-present Soldiers, the look reflected the streets as much as it influenced them. “The Workout ‘Soldier’ was the shoe with the NOLA youth. The southeast at this time was a “hot bed” for producing that good ole southern music with a funky beat,” said Hardaway.

There will always be that connection to street hustling for hip-hop and the fashion will always be a reflection of the world where rappers come from. As hip-hop has become globally influential, that culture influences the mainstream like never before. High-end fashion designers, runways and models are all taking their cues from what the streets do. That history is rich and varied, and a reminder that the most potent creativity tends to not come from the highest halls of privilege. It comes from the people. And hip-hop’s hustler spirit is well-earned.

Same as it ever was.

* Banner Image: Run-DMC, Jason “Jam-Master Jay” Mizell, Joseph “Rev Run” Simmons and Darryl “D.M.C.” McDaniels, circa 1980. (Photo by Laura Levine/Corbis via Getty Images)