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.”