Tailor Daniel Day, better known as Dapper Dan, is known for outfitting ’80s hip-hop icons in custom kits riffing on high fashion brands like Louis Vuitton and Gucci, who eventually sued his independent shop out of business for copyright infringement. But decades later, Dapper Dan’s memorable pieces are influencing what goes down the runways more than ever. Read this story and more in the latest issue of Highsnobiety Magazine.

The New Yorker’s version of the American Dream is only slightly different than the overarching ideal of owning a house that your family can pass down from generation to generation. The city has long praised the self-made individual, whether it’s a hustler who goes legit after a few brushes with the law, or the street-smart smooth talker who works his or her way up from the bottom of the ladder to the corner office.

Daniel Day, better known as Dapper Dan, occupies a space between those two archetypes. He grew up in Harlem, on 129th Street and Lexington, in humble means. He went to an elementary school three blocks away from where poet Langston Hughes lived. Whenever his mom won some money from scratch-offs, she’d treat him to a new pair of shoes. Soon, he was taking matters into his own hands, running the streets and shoplifting with a crew that included Richard “Pee Wee” Kirkland, who would go on to become a street ball legend.

Highsnobiety / Thomas Welch

Kirkland’s basketball talent caught the eye of the NBA, and the Chicago Bulls attempted to draft him in 1969, but he turned down the offer because the streets were already paying him in full. The drug game had a more handsome immediate payoff than professional basketball could. And this was the underworld where he and Daniel Day would cut their teeth, playing craps, gambling, and hobnobbing with uptown gangster greats like Nicky Barnes.

In fact, Dapper Dan earned his name not just from his signature sense of personal style, but because he hustled it from its previous owner—an older gambler who Day bested in craps. In a New York Times profile, Day says the man crowned him “the new Dapper Dan.” As for the older gentleman, he decided to go by “Tenor Man Dan,” since he happened to be a tenor saxophonist.

For Dapper Dan, style wasn’t just about self-expression. It was about embodying power and masculinity. As he puts it, a lot of the influence comes from the Southern United States, where prominent families ended up settling in the North.

“Those are the ones that said, ‘I’m gonna make it here, and I’m not gonna go back,’” he says. “A greater sense of fashion evolved among us that became like a powerful vehicle to all the people in the different areas of the South that we came from.”

In Harlem, masculinity informed the uniforms of some of the neighborhood’s most influential groups. The Black Panthers were usually clad in black leather blazers, powder blue shirts, black trousers and black berets, and their nattier counterparts, the Nation of Islam, often wore suits over crisp white shirts with bow ties and acetate-framed glasses. But in terms of burgeoning hip-hop style, underworld antiheroes like gangsters and drug dealers were the original style icons, using their gains to outwardly express their financial success.

“The rappers wanted to be like the gangsters, because the gangsters is the ones that had money. Then the hip-hop artists became rich, and they became the ones who everybody wanted to be like.”

Dapper Dan

“Hip-hop was influenced by the gangsters,” explains Dapper Dan. “The rappers wanted to be like the gangsters, because the gangsters is the ones that had money,” he continues. “Then the hip-hop artists became rich, and they became the ones who everybody wanted to be like.”

Indeed, in the early ’80s, hip-hop and braggadocio went hand-in-hand. Rappers wanted to look powerful and successful, so their outfits had to convey the same messages as their lyrics. A strong DIY aesthetic inspired by graffiti writers led to pioneers like Shirt King Phade gaining attention for his eye-popping airbrushed T-shirts and jeans, turning street art into early streetwear. It wasn’t uncommon to customize tees and jackets with iron-on letters to symbolize what crew you were representing. Slick Rick, Doug E. Fresh, Big Daddy Kane, and Eric B. and Rakim were all known for their flamboyantly masculine sense of style, pairing luxurious Bally shoes with layers of gold chains, cozy sweaters and casual sportswear from Nike, Fila and adidas.

But the high fashion houses they aspired to wear weren’t even speaking to the same audience as their music. Enter Dapper Dan, who opened his boutique at 43 125th Street in 1982. Like many of his customers that happened to be rappers, he was sampling street-ready silhouettes and mixing in pops of high fashion.

Highsnobiety / Thomas Welch

“The clothes just didn’t match the message and the sampling that the young people were bringing about,” says Dap. “They needed something that was consistent with the attitude and the approach toward their reality. And that wasn’t there for them.”

Brands like Gucci, Louis Vuitton, MCM and Fendi were already popular amongst the hip-hop community, but many of its members couldn’t even fit into the ready-to-wear offerings. So what Dapper Dan did was put these brands in a new context, combining covetable fashion houses with more generous fits and shapes that spoke to a younger, more discerning audience. And more importantly, he turned the clothes into wearable status symbols.

“The symbol of success is in the logo. I mean you could wear the fine garments, but kids would need to know that these garments cost money,” he explains. “The more of the logo you have, the more expensive the garment seems, and it looks like you arrived. The logo was saying: ‘Okay, I made it.’”

In addition, as Nas points out in the 2015 documentary Fresh Dressed, what Dapper Dan offered his customers was a certain unpretentiousness, and like any good tailor, a more accurate understanding of what his clients wanted. Sure, there were people in the hood fortunate enough to be able to step into a Louis Vuitton or Gucci boutique and cop some gear, but, at the time, they were treated much differently than the labels’ typical old-money customer. Not to mention, their selection was limited to just select leather goods and accessories, not full-on ready-to-wear collections, which would only begin to be introduced by labels like Gucci and Louis Vuitton in the early 1990s. In the same documentary, Dap describes what he did as “black-inizing” the appeal of these labels, making them look even better on his customers than the brands themselves.

“The more of the logo you have, the more expensive the garment seems, and it looks like you arrived. The logo was saying: ‘Okay, I made it.’” — Dapper Dan

Dapper Dan

Dapper Dan claims his boutique stayed open 24/7 for ten years, and had an after-hours window where late night clients could come get work done. The store was shut down in 1992 after cops raided his shop and multiple labels hit him with copyright infringement lawsuits. Among the myriad of people that worked for him was Darold Ferguson Sr., another hip-hop clothing legend known for screen printing T-shirts for labels like Bad Boy and artists like Heavy D, Bell Biv DeVoe and producer Teddy Riley. He met Dapper Dan when he was just 13, and at the time was a graffiti writer. Dap mentored him and even allowed him to put his work on some of his clients’ clothes. That relationship enabled Dap to serve as a mentor to Darold Ferguson Jr., better known as A$AP Ferg.

Highsnobiety / Thomas Welch

“My generation—that’s what we did, mentor the young guys,” says Dap. He’s seated in the salon of the Harlem brownstone he bought in the mid-’80s. The decor includes a bust of Barack Obama, and African art he picked up during a trip to the continent in 1974. It’s tasteful and homey, accented with forest green velvet couches and a dark walnut brown spiral staircase that frames photos of his family in the vestibule. It aligns with his personal sense of style—classic suits, shirts and furnishings of his own design. The way Dap dresses now couldn’t be more far removed from the ostentatious logomania gear that helped him buy
the house.

He calls A$AP Ferg on his cell phone, addresses the younger Ferguson as “nephew,” and asks him to come over for his Highsnobiety shoot. Ferg literally has just landed back in New York after a trip to Los Angeles to promote his third studio album, Still Striving, but promises Dap that he’ll make his way there as soon as he can.

Dapper Dan’s original boutique is now a school building, but that’s appropriate considering he’s still teaching the next generation. To walk around Harlem with Dap is to be in the presence of a mayor, perhaps even a king. He loves pointing out the history hidden in the rapidly-gentrifying neighborhood, motioning to a corner building that once housed Mike Tyson’s pigeon coop. During lunch at Street Bird, a restaurant by Harlem chef Marcus Samuelsson, Dap’s brand manager, his son Jelani, points out the numerous nods to his father in the interior design. A corner features a photo of one of Dap’s more famous pieces, a fur-paneled, balloon-sleeved jacket with Louis Vuitton monograms on the sleeve designed for Olympian track-and-field athlete Diane Dixon.

This same jacket would come back into prominence when Gucci’s Alessandro Michele presented a similar design on the runway in its 2018 Resort collection. In response, Gucci contacted Dap, and through a deal brokered by Jelani and Steve Stoute, CEO of brand development firm Translation, recently confirmed it is not just collaborating with Dapper Dan, but reopening his Harlem atelier, later this year, where he’ll have access to genuine Gucci fabrics to make officially licensed bespoke creations.

It’s ironic that his logo-laced designs are finally being proven as ahead of their time. But there are two main reasons Dap thinks that super-prominent branding is so relevant in modern fashion.

“There’s nothing that over the last 30 years that has been able to replace the logo. Logomania, it’s almost like it’s here to stay,” he says. “Nothing signals success more than your logo. I mean, if you had a Rolls-Royce and you didn’t have ‘RR’ on it, it’s not a Rolls-Royce.”

Dap also reasons that with plenty of minorities coming up in the world and getting more disposable income, they are forever tempted to display their newfound wealth. And savvy brands are picking up on this new market.

“They not only recognize that, they recognize the influence that the minorities have because of social media and hip-hop music on [culture],” he asserts. “So it was a natural evolution for them to reach down. Old money doesn’t need culture.”

Highsnobiety / Thomas Welch

A$AP Ferg meets Dapper Dan outside his Harlem brownstone, clutching a Fendi pouch and wearing a beat-up pair of checkerboard Vans Old Skools, a white vintage Nelson Mandela shirt, and white sweatpants from Ice Studios—a brand run by his girlfriend, photographer Renell Medrano. Though best known for music, Ferg has been carrying his father’s torch in fashion since 2005 when he launched his first brand Devoni Clothing. He made luxurious belts and bracelets that ended up on celebrities like Chris Brown and Swizz Beatz.

Even after the launch of his debut album Trap Lord in 2013, Ferg continued his career in fashion, starting a clothing line with the same name. He and Dapper Dan exchange pleasantries before sitting down in the salon. They start talking about life, Harlem, and how the A$AP Mob is taking what Dapper Dan and his contemporaries started to a new level. Mentioning how Harlem style has always been linked to the South, Ferg points out that A$AP Rocky grew up in Harlem, moved to the Bronx, then moved down South, helping form his unique identity. Ferg meanwhile is a trained artist, and went on to major in fashion and minor in fine arts in school. These disparate elements form the backbone of what makes A$AP Mob so unique.

For Ferg, his relationship with Dap isn’t just important because of the fact that he mentored his father, but because he believes that the younger generation needs to learn more from the old guard. Knowing about the past is a great way to learn about how to shape the future, especially when someone like Dapper Dan is more than willing to pass on his generation-spanning knowledge.

“You don’t got the OGs that wanna be an OG, like what [Dapper Dan’s] telling me: ‘I’m passing the torch to you so you can run with it. You run with the baton.’ Everybody wanna be in the game.”

A$AP Ferg

“We have no guidance. And the thing is, you got the old niggas trying to be young. So that’s what’s messing it up too,” says Ferg. “You don’t got the OGs that wanna be an OG, like what [Dapper Dan’s] telling me: ‘I’m passing the torch to you so you can run with it. You run with the baton.’ Everybody wanna be in the game.”

“My generation needed to give your generation your chance to shine,” replies Dap.

Dap is practically beaming as he speaks to Ferg, complimenting his current success and what the A$AP Mob has managed to build. They’ve made Harlem style a universal language, and more importantly, they’ve put the neighborhood on the digital map. “They took swag and made it virtual reality. They took it around the world, man,” says Dap.

“We was showing the world how we did it. And paying homage at the same time to what we grew up seeing, but at the same time adding our twist to it,” adds Ferg. “We just wanted to be noticed. It went from us taking over Harlem and being young up-and-coming celebrities to saying: ‘If we did this to Harlem, we could do it to the world.’”

Ferg explains what the A$AP Mob was initially doing as “dressing for sport,” wanting to flex on other people when they went out to events. It harkens back to what Dapper Dan said about style being inextricably linked to an expression of masculinity. But now, it’s not enough to dress well—you have to dress better than everyone else.

Highsnobiety / Thomas Welch

In another callback to Dapper Dan’s generation, Ferg recalls how for A$AP Rocky’s “Peso” music video, they were still a bunch of kids from Harlem rolling dice and hitting up the corner store, but now decked out in their own signature style. In those days, the A$AP Mob was known for wearing all-black outfits with an exaggerated gothic edge, accented by aggressive kicks from Raf Simons, Rick Owens and Jeremy Scott for adidas.

“We formed like Voltron. Not only did we form, we transformed. A$AP was just a street thing. We all came together and made it
a business,” says Ferg. “That’s when it just exploded.”

Dapper Dan’s DIY approach to fashion aligns with how Ferg and the A$AP Mob have taken the garments available to them, and put that clothing in a new context. Dap was taking symbols and pieces and translating them for the streets, while A$AP Mob’s legacy is taking runway garments and wearing them in their own way. And it’s exactly why A$AP Rocky has collaborated with labels like Guess and J.W.Anderson and has been the face of a prestigious house like Dior.

Dap couldn’t be prouder of the ascension of Harlem’s new fashion guard. They’re expanding the path that pioneers like him paved, and hip-hop culture has gone from looking up to fashion labels to one of the most important influences in modern style. Dapper Dan may have been the first to translate the language of fashion into hip-hop vernacular, but the A$AP Mob is expanding the lexicon.

“Let’s imagine A$AP Rocky never ever mentioning clothes,” posits Dap. “How much substance would that take away from his presence and from his artistry? They go hand in hand.”

This story originally appeared in Highsnobiety Magazine Issue 15, which is available now from our online store, as well as at fine retailers worldwide.

Words by Jian DeLeon
Editorial Director

Jian DeLeon is the Editorial Director at Highsnobiety. He is based in New York.