Even though he’s attained legendary status in the fashion industry, Harlem designer Dapper Dan still takes public transportation at least once a day. Seeing young people out in their natural habitat, he explains, keeps him attuned to culture at the moment.

“I take the bus every day, take the train, walk so that people can see me,” he told Gothamist in an interview. “Young guys see me on the train and say ‘I never thought I'd see you on a train’ – I say, ‘I'm on the train so I can see you.’”

There’s a practical reason for his transit choice, too: “My approach to fashion is like if they see me and they like the way I dress and things like that, I can reach young people.”

Remaining relevant to the masses and committed to his fashion vision while “translating” culture into a hot product has always been important to Dapper Dan, who was born Daniel Day in 1944 in Harlem. The designer says he’s continuing that mission in his third and latest collaboration with clothing and accessories retailer Gap: a collection of hoodies that blend the signature Gap logo and Dapper Dan’s name into “Dap.”

This new release, introduced exclusively in Harlem on Tuesday and available online starting Wednesday, includes a variety of colorways to celebrate the holidays. Some hoodies even feature the word “Harlem” to honor Dan’s neighborhood. In addition to signing merchandise on Tuesday morning, Dan helped launch a new series that afternoon — Gap House Sessions, in which he appeared with the Brotherhood Sister Sol, or BroSis, an organization focused on educating, organizing and training for social justice. (Gap announced plans to continue hosting sessions, and is donating $100,000 to support BroSis initiatives.)

BroSis co-founder and Executive Director Khary Lazarre-White (left), Dapper Dan (center) and rapper A$AP Ferg (right) address the audience at the inaugural Gap House Session.

“Gap and Dapper Dan have a shared commitment to celebrating individuality and encouraging others to have the confidence to be your true self — your best self,” said Len Peltier, Gap's global creative director. “Dap’s a fashion innovator shaping culture, and we are thrilled to continue to work with him as our partnership evolves with this latest drop.”

Dapper Dan says he’s elated that his hoodies have been well received – the last two drops sold out in minutes – but what’s more important to him is the message behind the medium. Since Trayvon Martin’s death, he explains, he’s had a strong desire to rehabilitate the often-vilified oversize garment.

“I've been having this feeling about hoodies, and how they always represent a hoodie as being dark, sinister or criminal,” he said. “So when they offered me this opportunity to be on a famous Gap hoodie and have it say ‘Dap’ instead, I say, this is a perfect opportunity for me to destigmatize the hoodie.”

Reimagining classic logos is nothing new to Dapper Dan, who rose to prominence in the early 1980s by designing leather clothing that incorporated the monograms of luxury fashion houses like Louis Vuitton, Gucci and Fendi.

“At the time, Louis Vuitton wasn't even making menswear,” said Senam Attipoe, a student and fashion enthusiast. “They were just making like the trunks and suitcases and everything. But he used their crest and he made it into a monogram logo, then he printed it on clothes. And that was never seen before, not even by the brands that he was using.”

BroSis youth members modeled Dapper Dan's newest creations at a launch event in Harlem.

Dapper opened a boutique named after himself in 1982. His designs caught the attention of early hip-hop legends like Salt-N-Pepa, LL Cool J, and Eric B. and Rakim, who wore his creations.

“Logomania today is still even a huge deal, and he did that,” said Sidney Cole, a fashion social media influencer. “He pioneered that idea. He created it. He added something that was necessary, especially for Black culture and fashion.”

Dapper Dan’s illegal use of designer logos caught up to him when his boutique was raided and shut down in 1992. He continued designing, and saw a major resurgence in 2017 when his online supporters accused Alessandro Michele, Gucci’s creative director, of copying one of his designs.

“It was this fur jacket with these balloon sleeves, and the sleeves had the monogram logo on it,” Attipoe said. “The internet just blew up over it.” That set the stage for Dapper Dan working directly with Gucci on a collection.

“Maybe it’s hyperbolic, but I look at the logo monogram pieces and the sweats and all of those things, and I just think about how none of that would exist without him,” Attipoe said.

Yet even with a career that spans decades, Dapper Dan says he’s still shocked that new generations know who he is.

“Doug E. Fresh is a generation younger than me,” Dan said, “and he calls me up, and he says, ‘Yeah, my son is bugging me in depth about introducing him to you.’ It keeps surprising me that young people are so attached to the foundation.”