The Evolution of Hip-Hop Fashion

“I went to class looking sharp, always living up to my street name even if I wasn’t in the streets,” Dapper Dan said in his 2019 interview with Vanity Fair. “That was the era of bell-bottoms and platform shoes, and when I mixed those with the exotic clothes I’d brought back from Africa, I was a sight to be seen.”

Dan, born Daniel Day, opened his first haberdashery boutique in Harlem in 1982. For the next decade, Dan’s boutique would import bootlegged fabrics and illegally screen-print luxury brand logos onto custom, street-style pieces that were often more expensive than the originals. Coinciding with the rise of hip-hop music, Dan’s boutique attracted a variety of artists and later became known as the embodiment of ‘70s hip-hop fashion.

Hip-hop, born out of the underground Black and Latino communities of New York City, rose to global prominence in the past 50 years as a culture and art movement for the disenfranchised. Hip-hop’s look was as integral as its sound, serving as a form of self-expression and an indicator of financial success.

“Fashion has always been an important part of the hip-hop identity because fashion has always been an important part of Black identity in America,” said producer and filmmaker Sacha Jenkins, director of the hip-hop fashion documentary “Fresh Dressed” (2015). “Because when you don’t have much ownership over where you can land in society, your financial situation, [or] your educational situation, the one thing you can control is the way you look.”

Late ‘70s to Mid ‘80s

Between the late ‘70s and the mid ‘80s, the rise of hip-hop fashion followed the commercial rise of rap music. Hip-hop fashion was a mixture of two aesthetics: sportswear and prep; both stressed prestige and wealth and tied back to Africanism. The hip-hop “standard” would include black (sometimes leather) tracksuits, Kangol bucket hats, Adidas or Puma trainers with fat laces, and heavy gold jewelry, which was popularized by performers such as Big Daddy Kane and Roxanne Shanté.

But hip-hop’s focus on the grittier sides of street culture made high-end brands such as Polo, Timberland, and Tommy Hilfiger wary; they were accustomed to white upper-class customers. The exclusivity of these brands, however, had unintentionally made hip-hop style more enticing.

In a 2004 BlackBook magazine interview, rapper Jay-Z stated that the inclusion of luxury fashion in hip-hop culture was his way of “living it on our terms, instead of trying to emulate an elite lifestyle.”

Dan’s legendary fashion trends also made a recurrence in the ‘80s, widely known as “blackenize fashion.” His clothes of this era personified street culture and the struggles of people who were young, Black, and rich but could not enjoy the luxuries of white people due to geography and race. “He drew on a long legacy of Black style as both a form of self-realization and a statement of political-aesthetic resistance,” said Rachel Lifter, assistant professor of fashion studies at Parsons School of Design.

Wearing a Dapper Dan piece was a sign of a successful hip-hop career. But by the early ‘90s, Dan’s popularity caught the attention of fashion industry lawyers. Dan had no choice in 1992 but to close his boutique and continue his business underground, selling his clothing through discrete road trips throughout the country. For the next quarter of a century, Dan was still active and revered as a hip-hop icon but out of the national spotlight.

Late ‘80s to Early ‘90s

Artists like KRS-One and Public Enemy coupled their anti-government, anti-police stance with the rise of Black nationalism in the late ‘80s. Black nationalist colors of red, black, and green became popular in the hip-hop scene, in addition to protective hairstyles such as box braids. Loose blouse pants from rappers like M.C. Hammer and headwear such as Fezzes, Kente cloth hats, and kufis became ubiquitous as hip-hop shifted into the ‘90s.

Cross Colours, established in 1989, became the first exclusively hip-hop clothing brand. The brand’s proposition—“clothes without prejudice”—was specifically aimed at Black youth. They used their clothing to voice political and social issues in the Black community, gaining recognition from celebrities like Muhammad Ali, TLC, Will Smith, and more.

Following Cross Colours’s success, other labels saw potential in the market for authentic hip-hop fashion and expanded their focus. Nike collaborated with Michael Jordan to create the well-known basketball shoes Air Jordans in 1984. Other clothing brands such as Reebok, Fila, Champion, and Carhartt drew wide recognition after being sported by hip-hop groups such as Wu-Tang Clan and Gangstarr. Adidas also gained popularity after the band RUN-D.M.C.’s now iconic hit song "My Adidas" dropped in 1986.

Inversely, the hip-hop fashion of this time influenced high fashion designers. Isaac Mizrahi, inspired by his elevator operator who wore a heavy gold chain, featured a collection with hip-hop influences in the late ‘80s. Models wore black catsuits, gold chains, big gold nameplate-inspired belts, and black bomber jackets with fur-trimmed hoods.

Chanel also incorporated notable hip-hop elements into several shows in the early ‘90s. One clothing line presented black leather jackets and piles of gold chains with pearl accents. In another, models wore long black dresses accessorized with heavy, padlocked silver chains.

The transition to the mid ‘90s expanded the feminine spectrum of hip-hop fashion, led by the girl group Salt-N-Pepa, who sported both “boyfriend” looks and more sultry outfits. TLC and late R&B singer Aaliyah created trends such as baggy pants paired with cropped, tight tops that remain widespread today.

Mid to Late ‘90s

Hip-hop’s biggest stars started wearing increasingly extravagant clothing in the mid ‘90s. Sean Combs (aka Puff Daddy), along with icons such as Snoop Dogg, Notorious B.I.G., and 2-Pac, popularized this trend by drawing inspiration from the old-school gangster look of the 1930s and 1940s and calling it “ghetto fabulous.” Many rappers set aside previous trends in favor of classic gangster fashions such as bowler hats, double-breasted suits, silk shirts, and alligator-skin shoes.

High fashion brands such as Tommy Hilfiger, however, remained prominent in the hip-hop scene due to their “exclusive” reputation. Hilfiger pursued the continually expanding hip-hop market, featuring Black models in the company's advertising campaigns and having rappers like Puffy and Coolio walk its runway shows.

Additionally, hip-hop jewelry culture—featuring the new popularity of platinum and diamond Grillz—caught the attention of luxury brands like Gucci, Louis Vuitton, and 212 Diamond City, which began making appearances in hip-hop music videos and films.

Womenswear continued to grow as a submarket within hip-hop fashion. Female performers such as Lil’ Kim and Foxy Brown introduced glamorous, high-fashion feminine hip-hop styles, such as Kimora Lee Simmons’s fashion line of Baby Phat. Conversely, Lauryn Hill and Eve popularized more conservative styles that still maintained both a feminine and hip-hop feel.

Then came Pharrell.

2000s to Now

As the group N.E.R.D. (No-one Ever Really Dies) began receiving high praise for their heavy use of electronic, bass, and funk beats in the new genre of experimental hip-hop, lead vocalist Pharrell Williams became widely influential for integrating skate, Japanese streetwear, and punk influence into his hip-hop looks in the early 2000s. Hip-hop fashion, though already far from its original sportswear origin, began its new reputation as limitless in its experimentation.

Together, Harajuku fashion designer Tomoaki Nagao (Nigo) and Pharrell created the label Billionaire Boys Club (BBC), which debuted in Pharrell’s “Frontin’” (2003) music video. This video solidified the conjunction of hip-hop and skate culture. Though skate culture had long been a predominantly white, California-led subculture, the growth of street skating throughout the ‘90s linked the two initially distant scenes. At this moment, Pharrell—and his partnership with Nigo—helped combine elements of hip-hop fashion with aspects of street skating trends, unifying them under the umbrella term known as “streetwear.”

Artists like Kanye, ASAP Rocky, and Tyler, the Creator continued this movement of experimentation by encouraging other hip-hop artists to step out of stereotypes and expectations of what rappers should look like in the late 2000s. Hip-hop continued its expansion not only into high fashion, but also into the avant-garde world of fashion.

These two genres of aesthetics, in tandem, made this era of hip-hop fashion varied and unique. While many embraced mismatched pastel colors and unorthodox silhouettes, some already established icons developed a more muted style.

One of the most important moments of this era took shape in the form of Kanye’s 2009 collaboration with the globally revered fashion house Louis Vuitton (LV). Though Kanye’s more well-known collaboration with Nike, the Air Yeezy 1, would debut the same year, his LV collaboration signaled a bridging of the once largely one-sided relationship between hip-hop and high fashion.

Hip-hop’s core ability to remix has made it one of today’s most popular styles of dress. Now it’s common to mix high-fashion or preppy clothing with oversized sportswear items, and the idea that anything goes is an industry standard.

“I think people of color, poor people in America are masters of the remix. In so many ways, hip-hop is a reflection of society and environment, wherein folks who are denizens of the culture, do not see themselves, do not see themselves in mainstream culture,” Jenkins said. “[Their] defiant attitude and desire to reinterpret styles [serve] as a foundational principle of hip-hop fashion that has crossed into the mainstream.”