The Flatiron Building, with its landmark facade, is joining a growing list of classic New York skyscrapers that are updating and in some cases, reinventing themselves.The Flatiron Building.CreditCalla Kessler/The New York Times

But now, 117 years after the Flatiron opened, those floors are vacant. Lured by cheaper rents downtown and the chance to consolidate staff in a modern workplace, Macmillan moved to renovated floors in the Equitable Building on Lower Broadway earlier this month.

“My publishing life was born and raised in the Flatiron,” said Louise Penny, a best-selling crime writer who even has a Flatiron charm on her keychain. “Behind the breathtaking and famous facade was a rabbit warren, some might say rat’s nest. Books and files were piled everywhere.”

The literary agent Christopher Schelling is equally nostalgic. “Symbolically it means something,” he said of Macmillan’s move, recalling how he often warned his writers that the conference rooms inside the Flatiron were definitely not as stylish as the building’s exterior. But that this was part of the fascination of the place.

“Everyone loves coming to the building,” said Sally Richardson, chairman of St. Martin’s Press, who worked in the Flatiron for five decades. Ms. Richardson helped to organize a goodbye party that drew hundreds of former employees, including some who flew in from other cities.

Although the MAC Cosmetics and Argo Tea stores on the ground level are still bustling, the floors above have been silent since June 14, awaiting crews that will rip out dropped ceilings and sheet rock partitions, among other tasks.

“Right now the building is looking terribly shabby,” said Ms. Richardson, who also spoke of the idiosyncrasies of the heating system — built around cast-iron radiators — that meant she might start her work day wearing a winter jacket and end it in a sleeveless T-shirt. “It’s a quirky place.”

The Flatiron is not the only classic New York skyscraper that is reinventing itself. The Empire State Building recently underwent a major renovation that made it more energy efficient. The Chrysler Building was just sold, and the new owner considered turning it into a hotel. The top floors of the Woolworth Building, once called “the cathedral of commerce,” are now luxury condos.

Although it is unclear who the future occupants of the Flatiron will be, it will remain an office building, said one of its owners, Veronica Mainetti, president of the Sorgente Group of America, which specializes in sustainable renovations of historic buildings. “The building was born as a commercial property, and we want to keep it as such,” she said.

Harry Black of the Fuller Company, which built the Plaza Hotel, the Macy’s building and the original Pennsylvania Station, also erected the Flatiron Building, which was the first skyscraper north of Union Square. He commissioned the Chicago architect Daniel H. Burnham to design it.

Burnham’s skinny building — a clever architectural solution to an unusual lot — shot straight up from the ground, with no setbacks, its three sides covered with classically inspired terra-cotta ornamentation.

Critics hated it; The New York Tribune called it “a stingy piece of pie.” But the public “was mesmerized,” said Alice Sparberg Alexiou, author of “The Flatiron: The New York Landmark and the Incomparable City that Arose With It.”

There was no other large-scale development surrounding the Flatiron at the time, so the building’s odd shape would cause the wind to whip around it. Skeptics predicted it would blow over, but its sturdy steel-skeleton construction held up.

The Flatiron’s interior would not fare so well. The water-powered elevators were famously slow and leaky. Miriam Berman, who worked as a graphic designer in the building in the 1970s and ’80s and now gives tours of Madison Square, recalled that the elevator cabs “bobbed around when you arrived at your floor,” before settling.

When John Sargent, who was appointed chief executive of St. Martin’s Press in 1996, arrived to meet with the staff for the first time, it took him several minutes to ascend from the lobby. “Someone asked me what my plans for the company were,” he recalled. His response: “I’m going to get the elevators fixed.”

Mr. Sargent, an outdoorsy New York native who grew up in Wyoming and eventually occupied the top office of the building’s prow, became frustrated at the slowness of the process, so he came up with a publicity stunt: He would rappel down the side of the building in the presence of a newspaper reporter and photographer.

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