Cole founded fashion company Kenneth Cole Productions in 1982.

Unable to afford a hotel showroom for a New York shoe trade show, he named the company "Productions" to obtain a film permit to park a trailer, from which he sold 40,000 pairs of shoes in under three days.

• He served as chairman of the AIDS research foundation amfAR from 2005 to 2018.

• In 2020, he founded The Mental Health Coalition.