You can’t talk about hip-hop without devoting a massive part of the conversation to the rappers’ tailor, Daniel Day, better known as Dapper Dan. He’s dressed everyone from Rakim to Salt-N-Pepa to Jay-Z in his designs, which he spun using logos from fashion houses such as Fendi, Gucci and Louis Vuitton and sold out of his Harlem boutique. But while he emerged in the hip-hop era, his own story started in a more idyllic Harlem.

“Growing up in the ’50s, I saw Harlem the way it will never be seen again. I’m the last generation that saw Harlem before a drug epidemic. I saw Harlem when everybody left their doors open, when there was no mugging and mistreatment of older people … I never lost one friend to gang violence.”

Dap, who also wrote “Dapper Dan: Made in Harlem — A Memoir,” remembered the whole neighborhood emptying into churches on Sunday mornings.

“That didn’t change until the ’60s, the first drug epidemic. So I’m thankful for that early experience. It taught me who we really are, you know, and it saddens me that young people never knew the Harlem that I knew.”

He talked about how his father’s incredible work ethic rubbed off on him. His first hustle was shining shoes and he will tell you the best place to get a shoe shine is still in his own bedroom. But it was music that opened the world of fashion to Dap. His brothers loved the Rat Pack, and he said he noticed how Sammy Davis Jr., Dean Martin and Frank Sinatra dressed and shopped and how it gave them a “sense of cool.”

“But now, we got a hip-hop age. I say I can replicate that. If I can come up with ideas that will give, you know, people an identity that can interface with the music of the day … So how can I take that look and give it the same flavor that the jazz musicians took … But to be honest with you, my biggest inspiration on how to make something look cool came from me studying the zoot suit, what Cab Calloway in Harlem did with the zoot suit. The zoot suit is the beginning of street fashion culture on a high level.”

He opened his boutique on 125th Street, which drew rappers, celebrities and athletes including Mike Tyson fiending for his clothes, which became known as Logomania.

“I come from the poorest of the poor in Harlem. But when I put on something new, you know, and went downtown, nobody knew where I lived. I think it gave you a different feeling. And that’s the feeling I captured when I started Logomania. You might come out of the projects. You might come out of the dilapidated buildings that I grew up in. But if you get dressed and you go downtown, you’re not in that building, you’re in that new moment.”

Sure it was the hottest thing on the street, but fashion houses didn’t take too kindly to having their logos splashed all over another person’s designs. They went after him, time and time again. He was finally forced to close his shop in 1992, but life had an odd twist for Dap down the road.

In 2017, Gucci knocked off an old jacket Dap had made, and to make amends, they decided to work with him and set him up with his own atelier in Harlem. And in 2019, when the brand sparked a controversy when they put out a balaclava sweater that resembled blackface, he once again spoke out but he reiterated his commitment to working with the brand, instead of cutting ties with them.

He called it a “critical moment in public relations between the races.”

“Every industry needed a Jackie Robinson. So Jackie Robinson, with all the things that he had to go through, [nobody] told him, ‘Walk away.’ No, he had to open doors, and that’s what it’s about,” he said, adding “You cannot change things from the outside. You change things from the inside. We can’t get mad and walk away because we accomplish nothing like that. We will take an insult and turn it into an injury instead of prosperity.”

He got on the inside indeed. Once an outlier and streetwear renegade, he became part of the fashion establishment and remains there. In 2019, he attended the Met Gala, where he said A$AP Rocky impressed him the most.

“It’s not even so much what he put on, it’s how he walks in it. He is the one that makes it happen.”

Dap has dressed so many artists and celebrities and has a career that’s spanned decades. But his proudest creation? The clothes he makes for Floyd Mayweather Jr.

“He comes in with ideas and I translate his ideas and he takes it to the world. He knocks people out with it, literally. In the ring and outside of the ring,” he said.

It’s amazing that Dap has been relevant for so long, but he has a philosophy, which he said goes back to his days as a kid swimming in the Harlem River. Before he’d dive in, he’d throw a Popiscle stick in to see where the current was going. He applied that same principle in his work.

He said the artists let him know which way the culture was going. “I embraced whatever it is they wanted to look like,” he said. He urged young designers to “be creative … but look at those you are creating for and extract from them. You will never be obsolete because you’ll always be able to follow the current.”

Detroit native Jalen Rose is a member of the University of Michigan’s iconoclastic Fab Five, who shook up the college hoops world in the early ’90s. He played 13 seasons in the NBA, before transitioning into a media personality. Rose is currently an analyst for “NBA Countdown” and “Get Up,” and co-host of “Jalen & Jacoby.” He executive produced “The Fab Five” for ESPN’s “30 for 30” series, is the author of the best-selling book, “Got To Give the People What They Want,” a fashion tastemaker, and co-founded the Jalen Rose Leadership Academy, a public charter school in his hometown.