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Considered the oldest remaining skyscraper in New York City, the Flatiron Building was completed in 1903 and originally known as the Fuller Building. The 21-story commercial office tower, located just below Madison Square at the intersection of Fifth Avenue, Broadway, and 23rd Streets, was rapidly nicknamed the Flatiron Building after its unusual triangular footprint and its prismatic shape that resembled the irons of the day. Immediately it became one of the city's most recognizable and beloved architectural landmarks.

It was at the turn of the 20th century that the Chicago-based George A. Fuller's steel construction company decided to move to New York and commissioned its new office building from the renowned architect and urban planner Daniel H. Burnham. Burnham had directed the Chicago's 1893 World's Columbian Exposition and designed, with his partner John Wellborn Root, Chicago's famous Rookery, Reliance, and Monadnock buildings.

The 285-foot-high Flatiron Building was the tallest edifice north of the financial district at the time of its completion. Nevertheless, its most distinctive features are its location, characterized by the surrounding void of streets that makes it frontally visible from a distance and almost isolated as a single building in the urban fabric, and its unconventional freestanding silhouette, which resembles the prow of a slender and majestic ocean liner sailing northward. Alfred Stieglitz, who captured its dramatic appearance in photographs, compared the status of the Flatiron Building in the United States to that of the Parthenon in Greece.

Designed in the Beaux-Arts style and richly adorned with Gothic and Renaissance details of Grecian faces and terra-cotta patterns, the Flatiron Building is structured like a classical Greek column. Its rusticated limestone façade is divided into three horizontal parts: a five-story base, a twelve-story shaft, and a four-story capital topped with a heavy projecting cornice. At its narrowest end, the building is just 6 feet wide, which from certain perspectives makes the structure look like a flat wall. This apparent fragility made many people fear that the building would collapse in a strong wind.

Actually, the extremely sharp angle at the northern end and the wind loads encountered at that location created special planning and framing problems that the engineering firm of Purdy and Henderson resolved by designing behind the eclectic Beaux-Arts skin of the façade a fully load-bearing steel skeleton structure reinforced with wind bracing. Also, the geometry of the site provided some major advantages, primarily the possibility for all offices to have an outside, wideview exposure. Consequently, the building has always benefitted from low vacancy rates in both its commercial and retail spaces.

Simultaneously, it became a tourist attraction and people enjoyed viewing the city from the observation lounge and restaurant located at the top floor of the tower. At ground level, the height and aerodynamic shape of the building led to a wind-tunnel effect that raised women's skirts and petticoats. It is said that the expression “Twenty-Three Skidoo” was born on the windy corner of 23rd Street when policemen had to tell young loitering men who came to peep at a lady's bare ankle to move away.

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