Dapper Dan & The Soul of Fashion in Hip Hop

Hip Hop was synonymous with fashion, both emboldened and emphasized through one another.

                        (Grandmaster Flash and the Furious 5, Courtesy of Fuse TV)

Hip Hop was a genre that embodied the soul and spirit of the community when the physical community was burning. The black and hispanic population of the South Bronx cultivated a new culture through music, dance, and fashion. An ode to the people and the struggle, a subculture was born out of oppression and strength of mind.

Even before emceeing and b-boy culture burst into the scene, there was a very present fashion deviation consciously breaking from the archetypes of mainstream fashion. Sneaker brands, headwear, furs and chains and the multitude of ways one can wear them defined the artists and the civilians with a voice. A 30-minute process of ironing, starching, and stretching your shoelaces was a true DIY that pulled focus to your sneakers. Fat laces were one of many ways to tamper and curate a desired perception of yourself. Sacha Jenkins, creator of “Fresh Dressed,” described fashion as a way to, “transcend the poverty that surrounded most of those involved.” Art has always been an outlet and a way to levitate above your reality. Hip hop was no exception. It was a space that was born from the mind and soul of the disenfranchised into something that transcended the heartache. The art of dress was inspired and molded by history and actuality, but fresh enough that it seemingly ignited out of nowhere and hip hop was the platform that gave visibility to what was already occurring in the Bronx, Harlem, Brooklyn. and Queens.

                     (The jean jacket as graffiti art’s first canvas in Brooklyn, circa 1983. Photograph: Jamel Shabazz/Cable News Network – Courtesy of The Guardian)

In the early 1980’s, hip hop was becoming prominent in mainstream culture. There were a select amount of rappers gaining economically from their art, which allowed for a different exploration of aesthetic. Harlem resident, Daniel Day, recognized the market for customized clothing within the community and jumpstarted some of the most iconic fashion trends in hip hop history. Better known as, Dapper Dan, Day recognized the significance of dress on the attitude of the individual. It was about dressing like royalty and feeling like royalty.

Dapper Dan grew up poor as a first generation Harlem resident. The lack of funds did not deter his interest in clothing and fashion. He acquired department store brands by his own means and was involved in the game at an early age. A stint in some local gang activity was short lived by his ideals of temperance. Further exploration led him on a journey to Africa through a program called The Urban League. The Urban League gave black and hispanic youth an opportunity to keep on a straight path through a summer in Africa. Julius Nyerere, president of Tanzania, prioritized the unity and empowerment of people, and with a socialist framework he strived for economic self-sufficiency. Inspired by African politicians such as Nyerere, and  after two separate trips to Africa, Dan was ready to serve his home and himself in a way he thought made the most sense. Recognizing fashion as a source of confidence and positivity, he worked at expanding the market. Initially he attempted to buy and sell clothes from local stores, but no one would sell to him. This led him to the realization that he could make his own. After careful observation of locals and their tastes and interests, Dan went about setting up his business. Hiring African seamstresses and turning his vision into a reality, his boutique opened in 1982 at 43 west 125th street. In a recent FIT interview, he described what being involved in the fashion industry has meant for him. He described it as a way,

 “to leave the streets and do something positive in the community that will change the way the community is represented.”

                       (Dapper Dan’s Harlem Boutique, 1984, Courtesy of Complex)

In a Vanity Fair interview Dapper Dan stated,

“I think fashion can escape a subculture. It’s that thriving, that beat within you to say, ‘I feel trapped. I gotta do this, I gotta be outside of this.’ That’s what fashion is to me. It’s a manipulative thing, too, because to me, there is no right or wrong in fashion. It’s just weak and strong. If an artist is great, that’s strength, and you can use his power.”

Without a sense of rules or hierarchy of taste, Dan was able to reconstruct fashion tailored to locals. Similar to what hip hop did for the community, Dapper Dan created a culture that was specific to the empowerment of black and hispanic people. Fashion was his power in a system that disenfranchised his demographic.

His business first attracted local hustlers and kingpins. With a strong sense of style and a disposable income, the gangsters defined style. Dan collaborated with his customers to perfectly tailor a style unique to them. Oversized pants were now fitted perfectly around the waist, but still baggy to appease the aesthetic. His observation of the popularity of brand names among hustlers struck him as something he could expand upon. Soon he was producing items plastered in logos that he silk screened on leather. Silkscreening, embossing, and designing were skills mastered through trial and error. Dan described the fundamentals of fashion and the nature of textile creation as something important in being a part of the game. He described this reconceptualization of brand symbols as an Africanization of high fashion, taking it away from the “Madison Avenue look.” His utilization of name brands and perfectly tailored garments made his shop famous.


(Dapper Dan and LL Cool J in a customized Jacket, Courtesy of Complex)

The Fat Boys were one of the first rap groups to visit the shop, then followed shortly by LL Cool J and Eric B and Rakim. Iconic hip hop trends seen on album covers stemmed from a desire to compete and emulate the power heads in the community. So while rap had affiliations with crime and violence, it was ultimately an expression of a reality and a way to rise above and escape. By this time, Dan’s creations were making regular appearances on Yo! MTV. In turn, it caught the attention of many of the European brands whose logos he was borrowing. By the early 90’s, Dan was sued and raided by a plethora of lawyers (Fendi being the brand that forced him into the shadows for his remaining years). Now he remains an independent, underground function, contently serving a select crowd.

As a result of Hip Hop in the mainstream came the popularity of “street wear.” Recognizing the innovation happening stylistically in the hood, black designers created a market catered to this specific demographic similar to the way Dapper Dan did, but on a more accessible scale. Cross Colours was one of the first brands in 1989 to utilize the subculture, their tagline being, “clothing without prejudice.” They aimed at spreading positivity and peace. They capitalized on bright colors and baggy silhouettes that epitomized the 80’s and 90’s. This sparked the rise of black designers in retail and high fashion utilizing street styles. Endorsed by many big names such as Tupac, Snoop Dogg, Dr.Dre, TLC, and Run DMC, these brands became synonymous with hip hop. Regardless of popularity, there was still a segregation in the fashion world between streetwear and the rest of retail. Department stores were hesitant to endorse these brands because of the stigma associated with hip hop, but over time there was an integration. Brands such as Cross Colours, Fubu, Karl Kani, and Sean John were seen on runways, and began to create a niche for themselves in the world of high fashion.

(Dr. Dre and Snoop Dogg, 1993, Courtesy of Cross Colours)

Today, we see the appropriation of black style by brands who did not embrace it until its globalization. The innovations of Dapper Dan are seen prominently in high fashion and mainstream retail, although he himself was repeatedly rejected from involvement in that particular market. In the last few years, Dan has come out from the underground to talk about his days on 125th street. Awareness of the inevitable gentrification of Harlem has led him to secure a spot on 125th where he still lives today. Collaborating with celebrities, interviewing for short films, and websites has made his story accessible. His first hand insight into the history of hip hop and fashion is valuable knowledge not to be overlooked. Ultimately, the hip hop movement is embodied by the attention to community and understanding that art can act as a form of enlightenment and transcendence.


Sanneh, Kelefa. “Harlem Chic.” The New Yorker. The New Yorker, 14 Sept. 2016.

Jenkins, Sacha. “Fresh Dressed.” Documentary. 2015

Tashjian, Rachel. “Why Harlem Legend Dapper Dan Doesn’t need Fashion Week.” Vanity Fair. February 13th 2015.

Dapper Dan. “Black Fashion Designers Symposium.” FIT. February 2017.

 Cochrane, Lauren. “So Fresh and so Clean: A Brief History of Fashion and Hip-hop.” The Guardian. Guardian News and Media, 27 Oct. 2015.

MP. “Dapper Dan On Taking Hip Hop Fashion From the Streets to the Runway.” Mass Appeal. N.p., 01 July 2015.

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