Daniel Day has been known as Dapper Dan since he was a teenager. He was making a living and a reputation shooting dice outside his high school, and an older saxophonist who previously had the nickname was watching him play. In his new memoir, Dapper Dan: Made in Harlem, coauthored with Mikael Awake, Day writes that when the man saw his “shined shoes and Continental pants and collared shirt, an admiring look spread across his face.” After Dancing Danny, as Day was then known, gathered his winnings, the man announced, “You the new Dapper Dan now.”

In 1982, Day opened Dapper Dan’s Boutique, his store in Harlem that, for the next decade, turned high-end logos into covetable, custom pieces for the hip-hop era. The book includes a pair of photo inserts featuring some of Day’s designs: Jam Master Jay in a Louis Vuitton–peppered bomber tracksuit, LL Cool J in a remixed Gucci jacket, Salt-N-Pepa in coordinating leather merch. On the way there, Day wrestled with addiction, tried his hand at journalism, took a trip to Africa that ended in a fateful shopping spree, and enrolled at Iona College for a bit. After dice, he mastered the burgeoning game of credit card fraud and, in one extended international venture, made plans to meet up with Patti LaBelle in Aruba but ended up in prison.

“I never looked at my life as journal material,” Day said in an interview last week, ahead of the memoir’s release on Tuesday. “I was too busy trying to figure my life out.”

Dressed in an ascot and vest, he certainly looked the part of a lifelong designer. But almost two thirds of Made in Harlem pass before Day’s celebrated boutique enters the picture. The Gucci collaboration that he’s worked on for the past couple of years is only mentioned in a photo caption.

Instead, Day undertakes an intense and exhaustive self-analysis. The memoir is a portrait of Harlem, fashion, and music over the course of his life, but more than any of that it’s a reconstruction of his ongoing spiritual exploration. “When you say ‘my work,’ you speak in reference to fashion,” Day said, “but what I’ve done in fashion, and in all my endeavors, is about looking for the angle. I was raised to do that. Looking for the angle, looking for the side that other people don’t see, when it becomes necessary for me to see something different.”

Day is a great talker. He answers queries in multiple paragraphs, with a healthy deployment of metaphor. When he’s not responding to questions, he’s providing his own. “If you’re standing on the mountain,” Day said, “you can’t see the mountain. You walked up to the mountain, so you have a better view, because you’ve been in the valley. So I’m actually like, What is it about the mountain that you see?” It wasn’t rhetorical.

Day closed his boutique in 1992 after a series of run-ins with establishment fashion’s lawyers. The constant raids ran him ragged and drained his funds. At the same time, his growing celebrity had made him a target in a world where many of his clients were big-name drug dealers. His 24/7 store had become a destination⁠—most famously embodied by a fight between Mike Tyson and Mitch Green outside its doors in 1988—and brought him the wrong kind of attention. So he went underground, and mostly sold his clothes in discrete fits on road trips throughout the country. For a quarter of a century, Day was still active, known, and revered, but his national profile was far quieter.

Then, in the spring of 2017, when Gucci’s Alessandro Michele showed a jacket that closely echoed an old Day design, the similarities were thoroughly noted on social media. It sparked a reexamination of Day’s work and his relationship to the brands that had once sued him for reframing their logos for hip-hop-age clientele. A broader cultural conversation ensued; Gucci eventually underwrote the reopening of Day’s atelier. He went back to doing his work in broad daylight, this time with a book deal. Jerrod Carmichael is now adapting Made in Harlem for a movie. For this past May’s Met Gala, Day dressed, among others, 21 Savage, Ashley Graham, Regina Hall, and Karlie Kloss.

Day viewed the surge in attention as welcome, if a bit perplexing and amusing. “You have to understand, it was a life of forced choices,” he said. Dice, he said, is still the subject he knows best; he hadn’t set out to be known for fashion. “Any one of those lives that I lived could have been my last life.”

“What is it that is this big attraction?” he wondered aloud. “I'm beginning to get it, but when you're born at the time I was born, you’ve seen so much, you know?”

Not that there haven’t been any perks.

“What I’m most happy about,” Day said, is that he’s “been greeted by, and have been accepted by, the king and queen of fashion. Princess [Anna] Wintour and King [André Leon] Talley.”

As much as a culture and an industry has had to catch up to Day, his core design philosophy appears timeless. He had a burst of inspiration shortly after opening his store when, after visiting a Gucci boutique, he realized that the only visible logos the brand was selling were on its garment bags. He stocked up on those bags to use in his own creations, and today he takes his use of logos as his enduring contribution to fashion.

“I deconstructed the brands down to the essence of their power, which was the logo crest, and reconstructed that power in a new context,” he writes in the book. “The names and the crests signified wealth, respect, and prestige. My customers wanted to buy into that power, and that was what I was offering.”

Laced throughout Made in Harlem is a developing conception of style and self-presentation. Even prior to his formal entry to selling clothes, Day had a nickname, and an eye for what an inventive attitude toward what clothes could do. When he wasn’t reading spiritual texts, he was flipping through issues of Vogue and GQ.

At Iona, he writes, “I went to class looking sharp, always living up to my street name even if I wasn’t in the streets. That was the era of bell-bottoms and platform shoes, and when I mixed those with the exotic clothes I’d brought back from Africa, I was a sight to be seen. My outfits excited people on campus of Iona as much as they did on the streets of Harlem.”

Day struck up a relationship with a tailor he met in Africa that set the stage for a collaborative view of design that became another of his trademarks. He opened his boutique to emerging creators such as Darold Ferguson, father of rapper A$AP Ferg, who now refers to Day as an uncle. Eric B. and Rakim bought from him—and put his work on their album art—but a young Fat Joe also worked at a nearby sandwich shop and would come by to talk rap. “The attention I give my customers when they come into the shop isn’t just a way to make people feel appreciated so they can keep coming back,” Day writes. “Listening closely is the key to my creativity. My designs are a response to the energy a client gives me. I thrive off that one-on-one exchange. I don’t think of myself as an artist or even as a couturier; I’m just using fashion to tell their stories.”

Not all high-fashion adventures are so closely tied to a sense of community, though, and Day’s partnership with Gucci hit one major roadblock in February, when the company started selling a balaclava sweater that simulated blackface. Calls for a boycott of the brand followed almost immediately. On his social media, Day wrote, “There is no excuse nor apology that can erase this kind of insult. The CEO of Gucci has agreed to come from Italy to Harlem to meet with me, along with members of the community and other industry leaders. There cannot be inclusivity without accountability. I will hold everyone accountable.”

Gucci soon issued a statement apologizing for the sweater, saying it would turn the controversy “into a powerful learning moment for the Gucci team,” and withdrew it from its stores.

“Gucci made a cultural mistake,” Day said last week. “I’m a product of a culture that’s been excluded, right? So now, when you bring these two forces together, the chemistry involved in that is explosive. So that’s why you heard me say, ‘I’m a black man before I’m a brand.’”

Day pointed to a crease in the restaurant tablecloth. He’d clearly talked about this before, and been asked to talk about it before.

“See this here? See this little line on the table?” Gucci was on one side, Day’s community on the other. “I’m sitting on the line.”

“Listen, they’re going to make amends for what they did,” he continued. “They’re going to open up doors so this don’t happen again. We formulated a change that involved people of color from all different aspects of the cultural world, of the corporate world, that can come up with ideas on how to change the culture. The corporate culture. So that this doesn’t happen again.”

“They have to iron this out. So this crease won’t be there anymore. So we can level the score.”

In other words, Day viewed the problem as an opportunity. The tension associated with his Gucci gig since its controversial genesis, he said, “enables me to get at the root of problems between people, between ethnic groups and racial groups. So that you can reflect and tell an even bigger story. I’m excited about that.”

Then again, if his memoir makes anything clear, it’s that Day has viewed just about everything over his whirlwind of a life as an opportunity. One of the primary recurring characters is his best friend and best gambling partner, Russell Poole. “It’s something about people who gamble, but don’t gamble,” Day said of the roots of their friendship. “Gambling is one of the biggest misnomers. Because when you gamble, you think it’s luck. And he and I both knew earlier on, early on, there’s no such thing as luck.” They bonded over a shared devotion to their craft, and what started out as a game outside school turned into a decades-long study and income.

But even while he was immersed in dice, Day was closely watching the world around him, knowing that he’d have to change course eventually. And in the end, it was one of his earliest insights that may have planted the seed of his fashion career. As a boy, he writes, “we scrutinized what the jazz guys wore…Nat King Cole, Dizzy Gillespie, John Coltrane were our fashion idols. Even though everyone wore dark suits in that era, the particular zoot suits that the jazz players sported brought something different, a flair to an otherwise basic design.”

A spate of lives and careers later, Day still finds himself returning to that mode of observation. “Early on,” he said, “my brain was rattling, and we see our cages open as we hear music. What the people of culture is known for is jazz. And whether people realize it or not, our jazz is in everything we do, and it didn't stop with fashion.”