Colby was born in Hoboken and raised in Jersey City. His parents took him into Manhattan frequently, and he was introduced at 13 by a neighbor to the Village vintage shops where he was drawn to the vintage denim, leather, and concert tees. He has always been attuned to and observant of street life—the attire of people walking past him and how their clothing expressed their personalities.
In high school he focused on the arts and later attended the School of Visual Arts and Fashion Institute of Technology. His favorite job was a six-year stint working for the vintage clothing company What Comes Around Goes Around (WCAGA), where he had shopped in the 70s for denim bell bottoms! There he learned the history of clothing. and moved up the ranks to director of vintage sales, where his clients included celebrities, designers, costume designers, and New York’s fashion elite.
Tamara Cepeda, a WCAGA coworker, gave Colby his first TV union gig as set costumer for MTV.