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Nothing is more of a buzz wrecker when you’re talking about cool than talking about cool.

It is not, after all, a quality one can anatomize or acquire. People possess it inherently or not at all, and those who have it are typically too smart to claim it. Those who lack it are well advised to find other virtues to cultivate.

That Dao-Yi Chow, 42, and Maxwell Osborne, 34, the designers who made their names with the streetwise label Public School, are cool has never been called into question. It is almost as much of a calling card as their skills at design.

They grew up in New York — Jackson Heights, Queens, for Mr. Chow; Kensington, Brooklyn, for Mr. Osborne — and met in the early aughts at Sean Combs’s streetwear label Sean John, where Mr. Chow was a senior executive and the younger Mr. Osborne an intern with no background or particular interest in design.

The two hit it off, though, and when in 2005 Mr. Chow opened a fashion boutique in Miami called Arrive, he brought in his former colleague to help him start a private label for the store.

They formed the label in 2008, calling it Public School in a nod to their city-kid backgrounds. Almost from the first they found a ready reception not just from mainstream editors but also from the style bloggers and influencers who, even then, were making an impact on the industry.

And while it took the pair a while to find their aesthetic footing, eventually they arrived at a signature style of layered, monochrome men’s wear, clothes that added tailoring to familiar slouchy elements of athletic and urban wear, rejiggering them as a new kind of masculine uniform.

The positive early critical reaction was matched by commercial success, and the two men — neither of whom has formal design training — were inducted into the inaugural group of the Council of Fashion Designers of America’s incubator program in 2010.

Then, in one of the abrupt changes of fortune so common in a fickle business, Public School was dropped by Barneys New York, which had accounted for more than half their orders, and Mr. Chow and Mr. Osborne shut the label down.

“Even now, we always think we’re one season away from closing the doors,” Mr. Chow said.

But that seems unlikely. In 2012, the two decided to double down on their vision and revive the label. Within a year, they had won the 2013 CFDA Swarovski Award for Menswear and the CFDA/Vogue Fashion Fund, which came with a $300,000 kitty.

They went on to score the 2014 CFDA Menswear Designer of the Year Award and the 2014/2015 International Woolmark Prize, simultaneously quadrupling the number of stores that carried the brand.

Then, last year, Mr. Chow and Mr. Osborne became fashion’s version of an indie band signed to a major label when they were tapped to be creative directors of DKNY, the accessible sibling line of Donna Karan International.

At the time of their hiring, the French luxury conglomerate LVMH Moët Hennessy Louis Vuitton owned the brand. But over the summer, LVMH agreed to sell Donna Karan to G-III Apparel Group, a manufacturer based in New York’s garment district that holds licensing agreements with Calvin Klein, Ivanka Trump, Levi’s, Tommy Hilfiger and the National Football League.

While LVMH and G-III are completing the deal, Mr. Chow and Mr. Osborne will present their third DKNY collection at New York Fashion Week before a tough crowd. G-III executives will be watching.

So will the industry supporters who, while they are rooting for this duo, are aware that critics questioned whether this mainstream brand and designers known for their downtown cool are a natural match.

Back to the Future

Go hunting for the source of the cool that Mr. Osborne and Mr. Chow so effortlessly project, and before long you may find yourself at a 12-story former Con Edison substation on West 26th Street. There, in 1990, a small group of New Yorkers got together to create a club they named Building, which became a necessary outpost of New York night life.

Though Mr. Osborne is too young to have made the scene at Building, Mr. Chow was a regular at the Thursday Night Train parties and Friday Powerhouse events where a dream roster (KRS-One, Run-DMC, De La Soul, Black Sheep, the Beastie Boys, Shabba Ranks, among many others) performed for a crowd that itself seems almost like an imaginary cross-section of New Yorkers — artists, photographers, designers, models, B-boys, downtown girls and celebrities like Russell Simmons, Sofia Coppola, Madonna, Bjork and Pedro Almodóvar. They were people famous for the old-fashioned reason: They had actual accomplishments.

“There was this sense of individuality then,” Mr. Chow said on a recent rainy summer day. “Everyone was figuring out night life, figuring out the bits and pieces that defined who they were.”

There was (as there has traditionally been in New York) a kind of accelerated cultural metabolic rate that kept people in search of the next new movement, talent, artist or scene. “It’s different now that everyone has access to the same information and the same things,” Mr. Chow said.

The designers were sitting at a table in a glassed-in conference room at Public School’s modest garment district headquarters. They had just returned from a DKNY trip to Asia and seemed faintly jet-lagged.

Nursing an ear infection, Mr. Osborne propped his head on his hand. The angular and athletic Mr. Chow leaned forward on his elbows, looking half-ready to pounce or to bolt.

If the two felt the pressures of rejuvenating the fortunes of a label that is, for the moment, effectively between owners, while also sustaining the identity of their own brand, it didn’t show.

It probably helped that critics heaped praise on the most recent Public School collections. Their latest women’s wear show, held in a blue-chip art gallery that once housed the Roxy nightclub, “conjured New York City in its wild, pre-gentrified days,” Maya Singer wrote in Vogue.

The Public School men’s wear show that followed it extended and amplified that impression, riffing on references to ’90s club wear: boiler suits and quilted parkas, leather Perfectos with floppy lapels, tunic-type shirts with clear origins in oversize throwback jerseys, flat-brimmed gunslinger hats.

After some wobbly seasons during which it seemed as if the demands of nascent fashion stardom had separated the designers from their creative wellspring (“We kind of lost ourselves,” Mr. Chow said), Public School appeared to find strength in a return to its aesthetic roots.

“Part of myself had been running from who we were,” Mr. Osborne said. “That was the first collection where we referenced something really personal, where we felt we could call friends from high school and say, ‘This is a collection you should really see.’”

Though there was nothing obviously retro about those collections, they resembled stuff anyone who happened to be there would have recognized from a bygone New York City, from a time when ransacking vintage emporiums, thrift stores, military surplus shops and the sale racks of obscure Belgian designers at Barneys to arrive at a style was not only a preoccupation but also a bona fide form of self-expression.

“We talk a lot about reappropriating,” Mr. Chow said. “It’s one of the drivers we always go back to. We take things that weren’t necessarily meant for us and redo them our way, for us.”

The most important and influential element of urban life in his clubbing days was the dancer, Mr. Chow said. “Whether it was at Building or Red Zone or Mars or Pay Day or Milky Way, the dancer was always the flyest person there,” he said. “I credit my creative drive to those five or six years of my life.”

Like so many who came of age in New York City high schools (Mr. Chow attended the elite Stuyvesant High School, Mr. Osborne Bishop Ford Central Catholic High School), the two men evince a sense of knowing, an awareness of how growing up in the city is an education in being tough and staying supple.

“It was a really good time, being a nomad in your own city, with your clothes for the night in a backpack,” Mr. Chow said of his high school years, when he roved around town with a posse of friends, doing all the things that cause concerned parents to lose sleep, if not, occasionally, their minds. “You were going to clubs or house parties, and you never knew when you might get home or whether you’d end up sleeping in an apartment and you didn’t know whose apartment it was.”

Mixing It Up

The packaging and retailing of that attitude is as good a reason as any why the pair was handed the reins at DKNY, a label that, as the designers said when they were hired, “evokes everything our city was always about: energy, disruption, new thinking and transcending all boundaries.”

DKNY had not signified any such thing for a long time, a fact of which the brand’s owners, were not unmindful.

And so it made perfect sense for a label that had begun to look as if it were designed by committee in Topeka, Kan. — despite the NY in its name — to try to revitalize itself by enlisting a pair of award-winning designers in possession of street cred and the ability to mix it up beyond the confines of the runway and showroom.

“Fashion exists in a world of make believe,” Mr. Osborne wrote in July, in an essay for W titled “Why I Stand With Black Lives Matter,” which chastened the industry for a lamentable lack of diversity. “As a black man in an overwhelmingly white industry, race is never far from my mind.”

Whether at Public School or DKNY, Mr. Osborne and Mr. Chow are less symbols or ambassadors of inclusion than a link to a less fragmented city and a time, one not all that long ago, when chromatic dispersion and diversity were civic givens, when the disparate tribes of New York came together to make music and art and fashion.

“I miss the old New York,” Mr. Osborne said.

“No, you don’t,” Mr. Chow said. ”You miss the old you.”