1980 : Becomes estranged from his mother and brother and sister, and opts to live with his paternal grandmother in her Beaux-Arts apartment in the Majestic on Central Park West. "I loved that she went to Saks Fifth Avenue to buy something, or to Bonwit Teller to buy a scarf, and Lord & Taylor to buy stockings," he will later tell Vanity Fair. He will later credit his grandmother, who teaches him to knit and brags about him to the butcher, as the biggest influence in his life. Through Parsons School of Design, takes a summer course on costume in Paris. Not wanting to leave, he cries on the plane ride home. Hanging out at Manhattan nightspots including Studio 54 and the Mudd Club, he aspires to the glossy lives of the artists and designers he bumps elbows with on the dance floor. "The idea of this glamour and hedonism was so fantastic, and I was just like this little voyeur, sort of dancing my head off on the sidelines," he will later say. He even hosts a fete for Japanese designer Kansai Yamamoto. "I had a ball," he will later tell The New Yorker. "I mean, I really did."
1999 : March: Receives the CFDA award for Accessories Designer of the Year. April: Duffy and other close friends and colleagues convince Jacobs to seek treatment for drug and alcohol addiction. "I was a crazy person. I was working and partying, working and partying," he will later tell Vanity Fair. "I kept looking over my shoulder and thinking, Well, this one does it, and that one does it, so I can, too. Because all designers are like that, and we're creative people, and that's how artists are."