More than 20 years after his name was on the label of an eponymous collection, the designer Steven Stolman is getting back in the game.

The Parsons grad has debuted a New York-made assortment that’s direct-to-consumer. Evening separates —  ballgowns, cashmere sweaters, taffeta skirts and tops — as well as dresses are familiar territory for Stolman. His resume includes stops at Pauline Trigère, Albert Nipon, Depeche Mode, Lilly Pulitzer, Jack Rogers, Scalamandré and Calypso St Barth. His styles were once sold at Saks Fifth Avenue, Bergdorf Goodman, Barneys New York and Neiman Marcus.

From 1995 through 2006, Stolman had a New York-based namesake business. With an initial investment of $60,000, he and his two business partners, a brother-and-sister duo, opened a freestanding store in Southampton, N.Y., and eventually added six more in Palm Beach, New York City, Nantucket, Beverly Hills and other locales. The socialite-turned-designer Pulitzer had encouraged him to do for the Hamptons what she had done for Palm Beach, he said.

After his partnership “went south and the texture of the business changed,” the business was shut down and Stolman walked away. “But I had to do it not just to save my sanity, but to save my life. It was just a toxic situation, and it broke my heart,” he said, adding that inventory controls, proper financial structuring and other guidelines were not in place.

The son of a periodontist, Stolman was born in Boston and raised in West Hartford, Conn. Three days after Stolman exited the fashion industry, he started working for a nonprofit leading a $9 million capital campaign to build Palm Beach County’s first federally qualified health center for the uninsured. A framed postcard from the photographer Bill Cunningham praising him for his efforts still hangs above his desk. Stolman has penned seven books including “Bill Cunningham Was There” with Cunningham’s longtime wingman at The New York Times John Kurdewan.

Over time the designer edged back into fashion with consulting jobs at Lilly Pulitzer and Jack Rogers. Digitizing his design portfolio a few years ago led him to having a hand in the RSVP collection at J. McLaughlin. Reminded how much he enjoyed designing, Stolman decided to dive back in. But he is well aware that many women want more relaxed, buy-now, and versatile styles. Stolman said, “Look at how I am dressed. This is all from Clare Waight Keller for Uniqlo. She is wonderful — she’s a friend. She inspired me to do clothes that are effortless, softer, and not so constructed.”

Relying on a sample room and factory in New York City’s Garment Center, Stolman has created a 10-piece line that retails between $600 and $1,200 that is being sold DTC at his own site, stevenstolman.com. He and his husband Rich Wilkie, an Oracle executive, plan to cap their investment in the venture at $100,000. Stolman declined to forecast annual sales. “Not expecting a huge business,” he said, “If it makes a little money and keeps me sane, why not? It’s not like I have any interest in playing golf or cards.”

Nevertheless, “the fear factor” still exists since he is a one-man operation, aside from production. Just as he started out two decades ago packing boxes on the ping pong table of his parents’ West Hartford home, the other day he was packing a shipment on the kitchen counter of his Chicago apartment. “I thought, ‘This is déjà vu with the Dennison tagging gun, wrapping the tissue paper and taking it to UPS myself.’”

While laser cutting, computerized label printing and other digital advancements have taken hold, Stolman said, ”the gentler aspects of the business” like draping remain. “That is very comforting to me that I can go back to the mannequin and still make the magic,” he added.

A pop-up launch event will be held by the Costume Council of the Chicago History Museum at the Women’s Athletic Club. His design ethos is akin to costume designer Rosi Gari’s wardrobe for Katharine Hepburn in “Summertime.” Based in the Windy City, Stolman and his husband also have getaways in Southampton and in Rancho Mirage, Calif. The pair often travel overseas too. “I have to make sure that the business is small enough and portable, so that it can go wherever I go. If it grows, as I hope it will, I will work with a fulfillment company,” he said. “But I’m no stranger to work. I know how to pull an order, pack a shipment, and do an invoice. It makes me feel really good to be back in the Garment Center, walking down those streets and into these buildings, and hearing those machines. It’s a comfortable place for me, because it’s where I learned to do what I do.”

As a Parsons student, Stolman won the Golden Thimble award, which was named for Trigère, who was also his critic. By the time he graduated in 1980, Seventh Avenue was awash with big-name designers like Bill Blass, Halston, Calvin Klein and Donald Brooks. “When I was going to Parsons, everybody wanted to be Calvin Klein, Donna Karan or Perry Ellis,” Stolman said. “I wanted to be Bill Blass, or Norman Norell. I’ve never been a sportswear designer. I’ve always wanted to design dresses.”

So much so, that he has treasured the cache of dresses from Norman Norell, Geoffrey Beene, Norell’s protege George Halley and a Mondrain from Yves Saint Laurent that a family friend Florence Pushker bestowed on him as a young man — so that he could learn how well-constructed frocks are made — and continues to use them as a point of reference. Like Blass and other long-gone designers from another era, Stolman relishes working with shoppers in stores (with a tape measure wreathed around his neck.) He laughed recalling how Trigère wouldn’t just tell skeptical shoppers that they could wear the dress that she had on, she would go into the dressing room to make them try her dress on. “Pearl [Nipon] did that too,” he said with a laugh.

As for today, Stolman said, “These are certainly some of the most trying times of our lives, and like Bill Cunningham said, ‘Fashion is the armor to survive the reality of everyday life.’ For a designer like me, that’s a call to action if I’ve ever heard one.”