[citation needed] With Kenneth Cole Productions painted on the side of the truck, they opened for business on December 2, 1982, in front of 1370 Avenue of the Americas.

They had a fully furnished forty-foot trailer, klieg lights, a director, a rolling camera, models as actresses, and two NYPD policemen as doormen.

A velvet rope allowed a limited number of people into the trailers and in two and a half days they sold forty thousand pairs of shoes.

In September 2021, Kenneth Cole announced a partnership with Nogin to re-platform their e-commerce business, which would help decrease costs and add AI-generated technology to its website.

In 1994, the company ran its first partisan political ad for that year's New York state gubernatorial race featuring George Pataki and Mario Cuomo, Cole's father-in-law.

His involvement with amfAR began in 1985 when he organized a public service campaign that was photographed by Annie Leibovitz and featuring high-profile models such as Christie Brinkley, Paulina Porizkova and Andie MacDowell.

In 2005, Cole spearheaded the “We All Have AIDS” awareness campaign with advertisements photographed by Mark Seliger and featuring Nelson Mandela, Tom Hanks, Will Smith, Elton John, Sharon Stone, Richard Gere, Elizabeth Taylor, Alicia Keys, Desmond Tutu, Natasha Richardson, Eric McCormack, Ashley Judd, Whoopi Goldberg, Harry Belafonte, Greg Louganis and Rosie O'Donnell as spokespeople.

He partnered with rock star Jon Bon Jovi to create a line of jackets, T-shirts and fragrance under the Kenneth Cole New York label.

[9] Kenneth Cole Productions has occasionally experienced difficulty adequately staffing its stores in order to properly rotate employees through mandatory rest and meal breaks.