How Dapper Dan Became Hip Hop's Leading Designer in the 1980s

by #LizPublika

Sewing Kit

It's impossible to have a conversation about hip hop culture and its aesthetic without mentioning the one and only Dapper Dan. Originally Daniel R. Day, the East Harlem-born designer and haberdasher is overwhelmingly credited with introducing high fashion to the hip hop world and the black community at large.

Day was born in 1944, just after the peak of the Harlem Renaissance, when horses and buggies still populated the streets and “white flight” hadn’t yet fueled economic havoc in the city. Still, Dan's rather large family — he was one of seven children — lived extremely modestly and he became a skilled gambler by the age of 13.

Though he just entered his teenage years, Dan had already developed a great sense of personal style, which earned him his famous moniker. It was bestowed upon him by his mentor on the streets, who saw the young man's ambition, style, and tenacity as attributes that would make him a successful swindler.

But a life of hustling soon took its toll. Dan developed a heroin problem by the time he got to high school and was arrested for dealing drugs by his early 20s. Incarceration, however, proved beneficial for Dan, who got sober within a month of entry by quitting cold turkey. A speech he heard by Malcolm X further made him want to change his life.

In the late 1960s, Dan began writing essays on Pan-Africanism for the Harlem-based Forty Acres and a Mule, started studying at the Countee Cullen Library and entered an academic program sponsored by the Urban League and Columbia University, which led to him touring Kenya, Uganda, Ethiopia, Egypt and Tanzania in 1968.

He returned to Africa six years later to witness the legendary fight between Muhammad Ali and George Foreman in what is now the Democratic Republic of the Congo. The event was postponed, but Dan never made it to the rescheduled match due to a chance meeting with an African tailor, who introduced Dan to suits that changed his life.

Dan became a clothier upon his return to New York. At first, he sold shoplifted items out of his car, but eventually saved enough money to open Dapper Dan's Boutique in 1982.

To accommodate the schedules of his more shady clients, he often stayed open late, operated seven days a week, and made himself available 24 hours a day.

“At first, the boutique sold furs. But when the girlfriend of a drug dealer came in with a Louis Vuitton purse, and Day saw the faces in the store all turn to look at it, he realized that the power of fashion went beyond aesthetics. He went to his local library to study the origins of the Gucci and Fendi logos and their evolution from mere hallmarks to status symbols. He understood what wearing a designer logo meant to his customers and how it made them feel.”

Unable to formally break into the fashion industry, the designer studied and worked on his own. “The first piece Day made was a jacket, which he trimmed with logo-printed canvas garment bags he had purchased from Gucci. The jacket was a hit after a client wore it to a party and everyone wanted to know where it came from.”

Soon, his designs became preferred to the ones made by the fashion houses he was ripping off. “His bold prints were synonymous with the bombastic style and braggadocio that was beginning to typify hip-hop – and Day was creating designs for the cream of that scene.”

If you can picture LL Cool J or Rakim in 1987, you're probably picturing them wearing something made by Dapper Dan. “Day’s ostentatious creations didn’t emulate, but rather amped up the luxury of existing labels, and he took to referring to them as ‘knock-up’ as opposed to ‘knock-offs.’”

Unfortunately Dan’s success was noted by the police who started to question the legality of his business practices and regularly raid his boutique. More misfortune followed and, after a successful trademark infringement case from Fendi in 1992, Dan was forced to shut down his boutique for good and returned to selling on the street.

Not one to quit on his dreams, Dan set up a smaller, more discreet operation in the home he shared with his wife and their kids in the late 1990s. Naturally, his best and most loyal clients followed and Dan resumed his business, trying to make lemonade out of the lemons he was dealt.

Things were going well, and then they got better. In 2017, a Dapper Dan jacket made for Olympian track star Diane Dixion in the 1980s suddenly found viral fame; apparently Gucci released a puff-sleeved mink bomber that was remarkably similar to Dapper Dan's with no creative attribution in a weird case of copycat-copying.

The subsequent public anger birthed a dream collaboration for Dapper Dan, when Gucci hired him to design a capsule collection and sponsored the opening of his own appointment-only atelier in Harlem, where he is still working today. In a remarkable turn of events, the man who ripped off high fashion became one its biggest stars.

How Daniel Day became Dapper Dan is both an extraordinary and familiar American origin story of self-determination. “Cultural appropriation and cultural exchange breaks down to one thing: economics,” he says. “An exchange involves somebody getting something, for whatever it is they have. Appropriation means you ain’t getting nothing.”