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.