J. Crew, the mass-market clothing company whose preppy-with-a-twist products were worn by Michelle Obama and appeared at New York Fashion Week, is expected to file for bankruptcy protection as soon as Monday. It would be the first major retailer to fall during the coronavirus pandemic, though other big industry names including Neiman Marcus and J.C. Penney are likewise struggling with the devastating toll of mass shutdowns.

J. Crew has been in negotiations with lenders on how to handle its debts for weeks, according to two people with knowledge of the situation, who spoke on the condition of anonymity because discussions were confidential. The retailer’s board was expected to confer on Sunday evening and J. Crew could file for Chapter 11 bankruptcy protection as soon as Monday, the people said. The company on Sunday declined to comment.

Retailers have furloughed employees, slashed executive salaries and hoarded cash in a desperate attempt to survive until the shutdowns are lifted. And there is widespread acknowledgment that J. Crew, which also owns the popular millennial denim brand Madewell, is not likely to be the only retailer to face the brink.

J. Crew was carrying a debt burden of $1.7 billion based on a leveraged buyout in 2011 by two private-equity firms — TPG Capital and Leonard Green & Partners — even before the coronavirus brought clothing sales to a near-halt in the 182 stores, 140 Madewells and 170 outlets it was running as of early March. And it had struggled to adapt to changing consumer tastes.

But in recent months it seemed to be making strides toward a more viable future. The company recently hired a new chief executive and was planning an initial public offering of Madewell this spring in order to pay down some of the debt and rehabilitate the J. Crew brand.

“Actually, this is a J. Crew ensemble,” Mrs. Obama replied, referring to her $148 yellow pencil skirt, $148 yellow and brown print tank top and $118 matching yellow cardigan. “Ladies, we know J. Crew. You can get some good stuff online!”

It was a priceless marketing moment. After that, everyone knew J. Crew, which seemed to embody the high/low mix-and-match trend of the moment.

The company was purchased by TPG in 1997 in a leveraged buyout from the founding Cinader family, and was taken public in 2003 — only to be reacquired for approximately $3 billion by TPG and Leonard Green & Partners nearly a decade ago.

Its creative director, Jenna Lyons, who had first joined as part of the design team in 1990, became a boldface name, known for her black-rimmed glasses, gangly frame and love of sequins and camouflage. Newspaper reports crowed about the comeback of the company’s chief executive, Millard S. Drexler, who had previously led Gap Inc. for years. Mr. Drexler, who goes by Mickey, became famous for riding his bicycle around the office and checking in with store associates via speakerphone.

In 2011 J. Crew became the first mass-market accessible brand to breach the high fashion parapet and present at New York Fashion Week. Vogue crowned the brand “a significant voice in the conversation on American style.” As the face of the brand, Ms. Lyons attended the Met Gala and, in 2014, played a role on the HBO show “Girls.”

Madewell, which filed for an I.P.O. in the fall, was expected to go public this spring while J. Crew remained private, but those plans were ultimately scrapped in March, which added a new wave of pressure and question marks to J. Crew’s future.

“The companies going into bankruptcy, for the most part, were companies that were struggling before Covid — we have not seen true Covid-only bankruptcies,” said James Van Horn, a partner at the law firm Barnes & Thornburg and a specialist in retail bankruptcy.

However, he added, “depending on how the current situation continues, that may change.”

For instance, Brooks Brothers, another quintessential American shopping institution, is already facing questions about its future.

“In the ordinary course of business, Brooks Brothers consistently explores various strategic options to position the company for growth and success, in partnership with its financial advisers at P.J. Solomon,” a spokesman said, in response to question about a potential sale.

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