Kenneth Cole and his daughter Emily Cole on Wednesday at the event hosted by the Cardozo FAME Center and the Cardozo Fashion Law Society.

Decades ago, Kenneth Cole believed himself on the path to law school when he was waylaid. A summer stint at his father’s shoe factory in the then dodgy Brooklyn neighborhood of Williamsburg opened new possibility, and that was that.

But the law, and trusted attorneys, were reliable companions as the company sprung from a daring enterprise out of a trailer truck more than 35 years ago, to an iconic international brand, Cole said Wednesday at an event hosted at the Cardozo School of Law near Washington Square Park.    

“The law is ever more important, as everything we do becomes more complex,” Cole told WWD. “And the infusion of social media has made a lot of things gray and undefined.”

Kenneth Cole was for a long time a complex business for its size, said Michael Colosi, its former general counsel, who now holds that position at WW International Inc., formerly known as Weight Watchers.

Cole’s business dealt with licensing, wholesale and retail issues on top of the more conventional intellectual property and corporate legal issues for fashion brands, Colosi said. The company has designed, marketed and licensed clothing and accessories under brand names including Kenneth Cole Reaction, Kenneth Cole New York and Le Tigre.

Kenneth Cole Productions Inc. was public for roughly two decades, trading at the NYSE as KCP, until 2012 when Cole took it private in a $245 million deal. At the time, the company brought in roughly $480 million in net revenues, and had around 1,600 employees, more than half of whom were part-time, according to its 2011 annual report.  

Colosi, who served as the company’s general counsel for 14 years until about 2014, oversaw a small in-house legal team there with a handful of attorneys, which worked with outside law firms including Katten Muchin Rosenman LLP. When Cole took the company private, he turned to the white-shoe firm Willkie Farr & Gallagher LLP for legal advice on the deal, according to SEC filings.

Colosi said his tenure at Kenneth Cole illuminated the increasingly business-oriented role that attorneys play at fashion brands, not just keeping them out of legal trouble, but expanding their place in the world. By the time the company went private again, it was running some 82 street retail outlets and dozens of shop-in-shops around the world, including in Asia and the Middle East, according to its regulatory filings at the time.  

“A really good general counsel can help a company achieve its goals,” Colosi told WWD. “You have to think hard about the questions you need to ask, and find ways to make an idea better.”

On Wednesday, Cole also reflected on his charitable legacy, addressing an audience of law students about intertwining his brand of social activism with his work. For instance, the company’s now-famous shoe drive in 1992 to support homeless New Yorkers, sprang in part from a business puzzle, he said. 

The company was doing business through department stores, and selling out its fall merchandise by February. That left the prospect of converting its inventory to summer sandals when “it’s still five degrees outside,” Cole said. “The dilemma was, how do you engage your audience?” he said. 

So the company held its first shoe drive in conjunction with Help USA, the homeless shelter group for which Cole has been a founding board member. The annual event, in which customers can donate “lightly worn” shoes to get a discount on a new pair, has collected more than two million shoes since, according to the company.  

Corporate brands might have traditionally distanced themselves from unpopular social causes to avoid alienating customers or investors, but Cole said he saw his approach as being about consistency.

“If a brand has a specific point of view and delivers on it, it has a reason to exist, and it becomes a destination,” he said.