Born to a Jewish family[1][2] in Brooklyn, New York, his father, Charles Cole, owned the El Greco shoe manufacturing company.

In two and a half days, Kenneth Cole Productions sold 40,000 pairs of shoes, while chronicling the beginning of the company on film.

The company has a wide variety of strategic partnerships for the production of men’s apparel, fragrances, watches, jewelry, eye-wear, and several other categories.

Kenneth Cole and the company have expressed a commitment to helping communities in need by supporting public health, civil liberties, and sustainability.

[6] He uses fashion as a medium to promote socially conscious ads to help fight various issues, from AIDS to homelessness.

In November 2017, sixty people including prominent AIDS activists signed a demand that Cole step down from his position after a federal investigation for fraud and money laundering was opened.

"[9] In August 2006, it was announced that Kenneth Cole Productions would stop selling fur in all of their garments for the Fall 2007 Fashion Season.

[13] The campaign is further promoted by a book "Awearness: Inspiring Stories About How to Make a Difference" featuring celebrities assisting various causes.

[18] In November 2011, Cole was honored by the Ride of Fame and a double-decker tour bus was dedicated to him in New York City.

[20] After outrage and much parody on the microblogging site and on the web in general, Cole deleted the entry and posted a personal apology on Facebook.

[22] On the West Side Highway southbound entering New York City, a billboard punned to southbound commuters, ”Shouldn’t Everyone Be Well Red?”[23] On Salon, David Sirota claimed that "Cole's campaign is thinly veiled ideological propaganda, and it comes with myriad problems, not the least of which is the simple fact that almost nobody believes "underperforming teachers" should be protected.

[6] One of his daughters, Amanda, hosted the Mets Kids Clubhouse for SportsNet New York cable TV network.