Dapper Dan, Gucci, and his Influence on Hip Hop

Mr. Day in his shop, Dapper Dan’s Boutique, which closed in 1992. He is wearing his own custom clothing.

Mr. Day confirmed on Friday that Gucci has contacted him. “We’re at the table,” was all he would say about it.

In addition to Gucci’s recent salutation, the Museum of Modern Art plans to include Mr. Day’s work in its fall show “Items.” In an email, MoMA’s senior curator of architecture and design, Paola Antonelli, called Mr. Day a “trailblazer” who “showed even the guardians of the original brands the power of creative appropriation, the new life that an authentically ‘illicit’ use could inject into a stale logo, as well as the commercial potential of a stodgy monogram’s walk on the hip-hop side.”

Mr. Day started down the road to sartorial splendor from 129th Street and Lexington Avenue, where he grew up with three brothers, three sisters, a homemaker mother and a father who worked as a civil servant. In 1982, after an apprenticeship that took him across Africa, he opened Dapper Dan’s Boutique on 125th Street. It lasted 10 years before lawyers from luxury brands moved in.

“What Dap did was take what those major fashion labels were doing and made them better,” said the rapper Darold Ferguson, Jr., who goes by the stage name ASAP Ferg and whose father, Darold Sr., worked at the boutique in the ’80s. “He taught them how to use their designs in a much more effective way. Dap curated hip-hop culture.”

Steve Stoute, the chief executive of the marketing firm Translation, said: “I think what Dap did, he actually taught an entire generation how to engage with luxury brands. Luxury brands, at that point, were not for us. They didn’t even have sizing for black people. So every time I walk into Louis Vuitton to buy a pair of sneakers, or buy a pair of pants in my size, I know they’re only doing it because of Dapper Dan.”

At his Harlem brownstone a few days before the Gucci controversy, Mr. Day described how his ideas on fashion, business and life in general came to be.

“My sense of style came from having holes in my shoes,” he said. “I was in third grade, and I would put cardboard and paper in the bottom of my shoes, but it got to the point where the soles were just gone. I just couldn’t take it anymore. I came home from church one Sunday and told my mother: ‘Ma, my feet are killing me. They hurt so bad.’ I had tears in my eyes. The next day, my older brother Cary said: ‘Come on. We’re going to the Goodwill on 124th Street.’ We got there, and Cary asked me, ‘You see anything you like?’ I picked out a nice pair of shoes on the rack and tried them on. Cary asked me, ‘How do they feel?’ I told him, ‘They feel good.’”

Another experience with shoes gave him an understanding of how clothes reflect social status.

“My mom bought me a nice pair of split-toe loafers with a tassel,” he said. “This kid from this snobbish family that lived in the brownstone next door to us began to tease me. He said, ‘Lily Day must’ve hit the number, because you got new shoes.’ I got so mad at that kid, because he was right. Every time my mom hit the number, she bought me and my siblings new shoes. But after those experiences, I started to do for myself. I was going through the window.”

With a group of other children from the neighborhood, he used to go downtown and break the windows of haberdasheries such as Phil Kronfeld and Fred Leighton.

His childhood friend, the Harlem basketball legend Richard Kirkland, known as Pee Wee, corroborated those stories in a short documentary made for Jay Z’s Life & Times blog in 2013. “They called us Ali Baba, like Ali Baba and the 40 thieves, because it would be like 40, 50 guys breaking the windows of clothing stores and jewelry stores downtown, yelling, ‘Ali Baba! Ali Baba!” Mr. Kirkland said.

Much of what Mr. Day and Mr. Kirkland talk about regarding the need to dress to impress is part of a generational mind-set for many black men who grew up in Harlem.

“My earliest experiences regarding race was in the home,” Mr. Day said. “I would listen to my mother and father talk about how the structure of white society was affecting us. I also remember Hulan Jack, who was the borough president of Manhattan, coming to my school, P.S. 24, to speak to us. This was a black man who was the borough president of Manhattan who came to tell our sixth grade class that knowledge is power. That fascinated me.”

Mr. Day’s pursuit of the American dream began in two seemingly different but analogous institutions: the street corner and the classroom. “I was a professional gambler as a teenager,” he said. “I would break all of the crap games on 123rd Street and Lenox. I would win big.”

He earned his nickname while playing craps, he said.

“The name was a combination of two things. I was the flyest young guy in my neighborhood. But there was also an older guy, a gambler, and his name was Dapper Dan. When I started beating this guy in the crap games, he said, ‘You are the new Dapper Dan.’ He was also a really great tenor saxophonist. He told me: ‘Just call me Tenor Man Dan. Now, you’re Dapper Dan.’”

Mr. Day grew tired of running the streets after witnessing speeches by Malcolm X. “Malcolm X once said, ‘If you want to understand the flower, study the seed.’ I was getting high at the time, but once I heard that, it stuck with me. I started going to the Countee Cullen library, and began reading about opium and the Boxer Rebellion in China. I said, ‘Oh, this is where it comes from.’ I connected myself to the problem of addiction globally. And I went back to school, courtesy of a program sponsored by the Urban League and Columbia University.

“I wanted to be a writer. I read books by Dr. John Henrik Clarke, Lerone Bennett. One of my favorite journalists was Earl Caldwell,” the pioneering black investigative reporter known for his articles in The Times on the Black Panthers.

Mr. Day worked for a Harlem newspaper called Forty Acres and a Mule in the ’60s and became aware of the sense of revolution around the country. “The young white kids were moving toward a spiritual, New Age kind of consciousness, and the people I knew were embracing black nationalism,” he said. “I personally was involved with the Nation of Islam, the Black Panthers and an organization called the Mighty Black Zulus. Not the Zulu nation of the Bronx, but a collection of brothers who dressed in black pants, green suspenders and red shirts.”

Mr. Day gave up drinking, smoking and drug use, and became a vegetarian. He toured Africa in 1968 as one of the students chosen by the Columbia University-Urban League program and returned for the Muhammad Ali-George Foreman bout in 1974.

“It changed my life,” Mr. Day said. “All of the artwork on the walls” — he gestured toward the paintings in his living room — “I brought those back with me from Nigeria. I also brought some suits over there. The tailors in Africa were making their version of a westernized, American suit.”

He decided that he wanted to be a clothier in his home neighborhood. He knew all the “boosters” — people who shoplifted from department stores — and he bought garments from them and resold them at a profit. He went from selling clothes out of his car to opening the boutique.

Photo

An outtake from the photo shoot for “Follow the Leader,” a 1988 album by Eric B. and Rakim. The rappers wore clothing by Dapper Dan. CreditDrew Carolan

In the ’80s he had enough capital to get serious about fur and leather, but many merchants would not sell to him. The exceptions were Fred Schwartz (known as Fred the Furrier), his brother Harold, and Harold’s son, Andrew Marc Schwartz, who started the Andrew Marc label.

Mr. Day began selling Andrew Marc leather jackets with possum lining for $800. A Harlem competitor, A. J. Lester, was offering the same goods for $1,200, and its representatives demanded that Mr. Schwartz stop supplying the upstart competitor. When Mr. Day and Mr. Schwartz considered a compromise — removing the Andrew Marc label from the jackets’ insides — Mr. Day had an epiphany about the importance of brands.

“The label is everything,” he said. “The label is the thing the gangster clientele use to let the other gangsters in the street know, ‘You ain’t got what I got.’ The label or logo sets you apart.”

Around that time, a man entered the boutique carrying a Louis Vuitton pouch. “This dude was bragging about the pouch,” Mr. Day said. “And it occurred to me, if that’s how he feels about the pouch, how would he feel if that Louis Vuitton pouch became a whole outfit?” He laughed at the memory. That was the moment everything changed. Mr. Day hired group of tailors, including Africans he had met in Midtown, family members and a friend from the Nation of Islam.

“I told this brother, ‘I have a lot of ideas, I just need you to do the cutting as I give you the patterns.’ I studied how he would sew the leather from the patterns of my design ideas. Clothes designing sounds fascinating, but it’s hard work. Folks don’t realize that there are limitations in the body form. We’re humans: We have arms, legs, chest. The exciting part of designing clothes is that you can be really creative within the context of those limitations.”

Mr. Day saw an irony in the fact that he was on the rise at a time when Reagan-era economic policies were damaging his home neighborhood.

“A lot of manufacturing businesses began selling off all of their equipment, because they were moving their operations offshore, to China,” he said. “As these manufacturers began to collapse in this country, I knew I needed to get in and salvage what they were leaving behind, so I could build my business. I remember going to an auction in Maine to get a particular machine that cut leather. Most times, I would be the only black guy at these auctions and I would ask questions of all of the experts who knew about the various machines. That is how I learned this business: by asking the right questions.”

At the same time, the crack epidemic was tearing neighborhoods apart.

“The Italians were slowly losing their grip on Harlem and a lot of young guys were moving in, because the price of cocaine began to drop,” he said. “Drugs were and are a curse on places like Harlem, but they created an economy that allowed my business to thrive. The street guys wanted to look good. I was juggling the polarity of Malcolm X and a big time hustler like Joe Jackson. Being a former street guy myself, I understood what was going on around me. I was in it, but not of it.”

The boutique often stayed open seven days a week, 24 hours a day. Dealers took Polaroids of the latest Dapper Dan designs in their wardrobes; those photos reached street hustlers from Philadelphia to Detroit to Los Angeles. “At 2 in the morning, people from as far away as Philly were shopping at Dapper Dan,” the R&B vocalist Jeff Redd said. “He changed the game in fashion.”

Samira Nasr, the fashion director for Elle magazine, likened Mr. Day’s work to that of the innovative hip-hop D.J.s of the era, such as Jason Mizell, a client of Mr. Day’s. Mr. Mizell, who died in 2002, created beats for Run-DMC under the name Jam Master Jay. “Sampling was taking existing music and slicing it to recreate new sounds for original lyrics,” Ms. Nasr wrote in an email. “Dap was sampling in a way. He was taking existing fabrications and breathing new life and beauty into them.”

Big Daddy Kane, Eric B. and Rakim, KRS-One and LL Cool J were among the clients who came for Mr. Day’s unique retrofits of Gucci, Louis Vuitton, Fendi and MCM. He worked the logos into his leather coats, hats, suits and even car interiors.

When asked to describe what he has been up to in the 25 years since his boutique closed, Mr. Day looked at his son and business liaison, Jelani Day.

“He went underground,” Jelani said. “There is more to the story, but that’s all we need to say for now.”