He graduated in 1981. He lived in Teaneck, New Jersey with his mother, sister and younger brother, and attended Teaneck High School. At fifteen, Jacobs worked as a stockboy at Charivari, an avant-garde clothing boutique in New York City. From there, Jacobs entered The New School in New York City. During his tenure at Parsons, Jacobs won the Perry Ellis Gold Thimble Award in 1984 and in the same year was also awarded the Chester Weinberg Gold Thimble Award and the Design Student of the Year Award.