Born on Nantucket Island, Massachusetts, Macy was the fourth of the six children born to a Quaker family. At the age of fifteen, he had a red star tattooed on his hand when he worked on a whaling ship 'The Emily Morgan'. This Red Star later on became the logo of the store. In 1844, Macy married Louisa Houghton and had two children and named them, Rowland Hussey Macy, Jr and Florence Macy.
Between 1843 and 1855, he opened four retail drygoods stores. These also included his original store in downtown Haverhill, Massachusetts which was established in 1851 to serve the mill industry employees of the area. Although all these attempts failed, he never losed hope. He successfully learnt from his mistakes. In 1858, Macy moved to New York City where he established a new store and named it "R.H Macy Dry Goods". This store was located in at Sixth Avenue on the corner of 14th Street, which was significantly to the north of other dry goods stores of the time.On the company's first day of business on October 28, 1858 sales totaled $11.08, equal to $297.09 today.
As the business grew, Macy expanded it into neighbouring buildings where he diversified it by opening up more and more departments. For publicising the store, Macy used various creative methods like illuminating windows display, theme exhibits and installing store Santa Claus. It also provided money back guarantees although it only accepted cash into the 1950s. The store also produced its own made-to-measure clothing for both men and women, assembled in an on-site factory.The shop later moved to the elite shop-spot of that time, the 18th Street and Broadway, on the "Ladies' Mile" where it remained for around 40 years.
In 1875, Macy took on his nephew and his cousins husbamd as his two partners. They were Robert M. Valentine (1850–1879), and Abiel T. La Forge (1842–1878) of Wisconsin.
He died of Bright's disease on March 29, 1877 in Paris . He was interred in the Woodlawn Cemetery in The Bronx, New York.
His will was probated on May 1, 1877, and he left his wife, Louisa H. "absolutely, all the paraphernalia, wearing apparel, watches, rings, trinkets, jewels, and personal ornaments reputed to belong to her, and during her life, the use of all the household furniture, books, clocks, bronzes, and works of art". At her death this was to pass to his daughter Florence. He left only a small annuity for his son. The following year, in 1878, Macy's partner La Forge died, and the third partner, Valentine, died in 1879. Ownership of the store passed to the Macy's family until 1895, when it was sold to Isidor and Nathan Straus.
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