In 1920, the New York office, now at 115 Fifth Avenue, included a staff of 17 buyers and support personnel. The New York buyers bought everything from housing supplies to clothing. When Sears began opening retail stores in 1925, the company discovered that the retail store customer was more fashion conscious than the catalog customer was. This increased the importance of the New York City buying offices.

In 1928, the New York office became Department 664 and moved to new offices at 881 Broadway. This office included the New York headquarters for the company’s Modern Homes catalog home program. Sears briefly experimented with employing a construction crew in New York City that built the larger catalog homes and contracted out for home remodeling.

In 1930, Sears purchased a quarter interest in the Henry Rose Stores (Henry Rosenzweigh owned the Henry Rose stores), a fashion company operating in New York City. The Henry Rose buying offices were located at 55 W. 13^th Street in New York City. The idea was to use the Henry Rose Stores to improve the company’s fashion lines. Sears management recognized that the company’s centralized buying system in Chicago could not keep up with the rapidly changing women’s ready-to-wear fashions. Sears contracted with the Henry Rose company to merchandise all ladies’ ready-to-wear and millinery in the retail stores around the country. The Henry Rose stores shipped ready-to-wear and millinery to all Sears store locations, set up the store displays, restocked the merchandise and shared in the profits. In 1944, Henry Rose became a wholly owned Sears subsidiary.

The Sears New York office, located at 360 W. 31^st Street in 1940, included over 128 buyers and support staff. Staff included a New York Catalog Production Manager, Group Credit Supervisor, Personnel Manager, and physician.

When James Button ran the New York office in the 1960s, the office included its own Public Relations department, Merchandise Development Design and Testing Lab, and a Fashion Merchandising Center.

By 1977, over 70 percent of the women’s wear that Sears bought came from the New York offices. The New York testing lab focused resources primarily on testing garments and fabric materials.

In 1978, Sears announced that the New York buying offices were moving to downtown Chicago in an effort to make operations more efficient. Sears completed this move in April 1979, officially closing the New York office, although some buyers did remain in New York.

Sears briefly had a store in New York City. In 1960 a Sears "B3" size store. The "B3" size store was a fairly small store stocking primarily softlines. This store opened near the company’s New York offices on 31^st street. Sears closed this store in 1965.