Born to a Jewish family in Brooklyn, New York, his father, Charles Cole, owned the El Greco shoe manufacturing company. Cole graduated from John L. Miller Great Neck North High School in 1972. Before learning the family business and starting his own company in 1982, Cole graduated from Emory College of Arts and Sciences of Emory University in 1976.
Kenneth Cole Productions, Inc. is an American fashion house founded in 1982 by Kenneth Cole. Wanting to preview his line of shoes at Market Week at the New York Hilton, but unable to afford the purchase of a hotel room or showroom to display his items, Kenneth Cole inquired about parking a trailer two blocks from the Hilton Hotel. Upon discovering that permits for trailers were only granted to utility and production companies, Cole changed the name of his company from Kenneth Cole Incorporated to Kenneth Cole Productions, and applied for a permit to film the full-length film, "The Birth of a Shoe Company". In two and a half days, Kenneth Cole Productions sold forty thousand pairs of shoes, while chronicling the beginning of the company on film.
In 1994, Kenneth Cole went public, and has been included on Forbes annual list of 200 Best Small Companies four times.
Kenneth Cole designs men's and women's footwear, men's and women's clothing, and also accessories under the Kenneth Cole Reaction Line. Overall, Kenneth Cole Productions sells clothing and accessories under the following lines: Kenneth Cole New York, Kenneth Cole Reaction, and Unlisted. The company now operates over 90 retail and outlet stores worldwide, and sells in catalogs and websites. Cole himself controls almost all of the voting rights and owns 45% of the company.
Support of progressive social causes
Since 1985, Kenneth Cole has been openly involved in publicly supporting AIDS awareness and research. He is considered the first in the fashion industry to do so. He uses fashion as a medium to promote socially conscious ads to help fight various causes from AIDS to homelessness. He has donated proceeds to such organizations as Mentoring USA, amfAR and Rock the Vote.
In 2001, The Kenneth Cole Foundation, in association with Cole's alma mater, Emory University, created The Kenneth Cole Fellows in Community Building and Social Change Program at Emory University.
Kenneth Cole's socially conscious advertising for the causes that he champions can be somewhat controversial. One such example was his campaign for World AIDS Day in 2005. He designed T-shirts for the campaign which were sold at such stores as Barneys New York, Scoop, and Louis Boston. The messages on the shirts stated either, "We All Have AIDS" or "I Have AIDS." Cole created the shirts in hopes that those with or without AIDS would wear the shirts, to help diminish the stigma attached to the disease. Cole stated, "There is a legend of the Danish king, Christian X, who, during World War II, when Hitler insisted all Jews publicly wear a yellow Star of David, would wear the star himself, hence making it difficult to differentiate who was Jewish. This is kind of like that, hopefully."
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.
In October 2007, Cole guest-starred in the Ugly Betty episode Betty's Wait Problem.
In the summer of 2007, Kenneth Cole Productions also began their "Awearness" Campaign, which will produce a line of T-shirts to benefit the charities that the company supports, and proceeds will go to the Awearness Fund. The campaign is further promoted by a book "Awearness: Inspiring Stories About How to Make a Difference" featuring celebrities assisting various causes.
On May 1, 2009, Kenneth Cole delivered Northeastern University's keynote address at the Commencement ceremony.
In 1998, People Magazine voted Cole as "Sexiest Businessman of the Year."
On May 14, 2009, The Legal Aid Society of New York City honored Kenneth Cole with its inaugural Theodore Roosevelt Corporate Award at the Waldorf Astoria during its Servant of Justice Award Dinner. Proceeds will go to benefit struggling New Yorkers who live in poverty. 
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.
On February 3, 2011, Kenneth Cole posted an update on microblogging website Twitter that referenced the 2011 Egyptian protests. The tweet, which indicated that Cole himself wrote the entry, said: "Millions are in uproar in #Cairo. Rumor is they heard our new spring collection is now available online at (website address) -KC". 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.
In April 2012, the designer started a campaign that included an attack on public schoolteachers and their unions portraying the national debate over education as one that pits “Teachers’ Rights vs. Students’ Rights.” On the West Side Highway southbound entering New York City, a billboard punned to southbound commuters, ”Shouldn’t Everyone Be Well Red?” On Salon, David Sirota wrote:
"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. That includes the nation’s biggest teachers’ unions, which have been outspoken in backing “accountability” reforms for teacher tenure. So right off the bat, Cole is constructing a straw man, one that has served over the years to pretend that public employee unions in general and teachers’ unions specifically are about nothing more than making sure bad employees get to keep their jobs."
In response to the negative outcry, his company announced on Twitter, "We misrepresented the issue—one too complex for a billboard—and are taking it down."
In 1986, Cole met Maria Cuomo, and they married a year later. Maria Cuomo Cole is the daughter of former New York Governor Mario Cuomo and sister of New York State Governor Andrew Cuomo and CNN journalist Chris Cuomo. One of his daughters, Amanda, hosted the Mets Kids Clubhouse for SportsNet New York cable TV network.
Kenneth Cole and wife Maria Cuomo Cole purchased a $14.5 million co-op in 2008 on Sutton Place in New York City. At one time, fashion designer Bill Blass lived in this same building.Cole, Kenneth, Awearness: Inspiring Stories about How to Make a Difference, New York : DK Melcher Media (November 3, 2008). ISBN 978-1595910462