At their first meeting, Mr. Chan recalled, Mr. Sternberg spoke philosophically about a series of microbrands, each with a unique reason for existence but none so overly distributed that it loses its voice. Mr. Sternberg did roll out the women’s lines Boy and Girl and, for a brief time, the sportswear-focused This Is Not a Polo Shirt (he later combined them under Band of Outsiders to avoid confusion).

“My first meeting with Scott was so refreshing,” said Mr. Chan, who now is head of international for Kate Spade. “I saw the opportunity for the brand was quite tremendous.”

Still, he said, he wondered where the scale and money would come from to sustain it all. “Each brand is requiring so much energy and resources,” Mr. Chan said. “The beauty was in the insanity.”

For all his ambition and drive, Mr. Sternberg seems to have had an ambivalent or perhaps naïve view of the business side of fashion. In a talk at the Hammer Museum in Los Angeles in 2013, he said that he had long thought of Band of Outsiders as “a platform to put ideas out into the world,” before adding, in an obligatory tone, “It’s also a business and we have to, like, make clothes and a margin and money and things like that.”

In his approach to design, manufacturing and pricing, there was a strange disregard for increasing the company’s sales in a way that would take Band of Outsiders beyond a niche brand.

The clothes were beautifully made. But how many men care that a polo shirt was sewn in Japan using ultrathin super high-gauge cotton pique? And of those, how many are willing or able to pay $175? And of that very limited demographic, how many have the body type to wear a shrunken fit?