Iconic Buildings

An extensive collection of vintage pictures of some of New York’s (and the world’s) most iconic buildings including the Empire State, Chrysler, Woolworth and Flatiron buildings, the Times Tower, Grand Central and Pennsylvania Stations, the New York Public Library, and more.

The Dakota Apartments, 1903

The Dakota Apartments, 1903

The Dakota Apartments at Central Park West and West 72nd Street is probably one of the most iconic buildings in New York City. Often remembered nowadays as the location of the murder of John Lennon by Mark David Chapman on December 8, 1980, the Dakota's place in New York history and in popular culture arises from more than that single tragic event. Aside from Lennon and his wife, Yoko Ono, the building's residents over the years have included many well-known New Yorkers, such as Lauren Bacall, Jason Robards, Jose Ferrer, Lillian Gish, Judy Garland, and Gilda Radner -- among others.

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Aerial View of Lower Manhattan, c. 1930

Aerial View of Lower Manhattan, c. 1930

In this eastern-looking aerial photograph of Lower Manhattan and Tribeca, taken around 1930, one gets a view of many of the most notable structures of the day, including the Woolworth Building, the Municipal Building, City Hall and the Post Office, as well as the Federal Courthouse, and the Brooklyn and Manhattan Bridges. Aside from the Woolworth and Municipal Buildings nothing in view could be called a skyscraper. It's is a very different Lower Manhattan Skyline than today's.

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Madison Square Garden, 1924

Madison Square Garden, 1924

The second Madison Square Garden, seen here decorated for the 1924 Democratic National Convention, was located at East 26th Street and Madison Avenue, where the New York Life Building stands today. This incarnation of the Garden replaced a more primitive open-air arena. Designed by the famed architect Stanford White in 1890, it was also the site of his 1906 murder by socialite Harry K. Thaw over White's affair with Thaw's wife, the actress Evelyn Nesbit. The building was designed in the Beaux-Arts style and boasted a roof garden restaurant.

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Statue of Diana atop Madison Square Garden, circa 1925

Statue of Diana atop Madison Square Garden, circa 1925

There was a time when Madison Square Garden was located at Madison Square, on East 26th Street and Madison Avenue, in what is today called the Flatiron District. In this black and white photograph, taken shortly before the demolition of this Madison Square Garden, we see the famed Statue of Diana by sculptor Augustus Saint-Gaudens. This is actually the second version of the statue. Both the sculptor and the architect of the building, Stanford White, thought the original was too heavy at 18 feet tall and 1800 pounds, so Gaudens made a shorter, hollow version.

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Pennsylvania Station, Prior to Opening, 1910

Pennsylvania Station, Prior to Opening, 1910

In 1910, the Pennsylvania Railroad Station, or Penn Station, opened to the public. The building, which was torn down in 1963 prompting the creation of New York City's Landmarks Preservation Commission, had been designed by the famed architectural firm of McKim, Mead & White in the Beaux-Arts style. The interior concourse, which you see in this black and white photograph taken just prior to the station's completion in 1910, was inspired by the Roman Baths of Caracalla.

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Empire State Building Under Construction, Late 1930

Empire State Building Under Construction, Late 1930

The Empire State Building may no longer be the tallest building in the world, but it is easily one of the most recognizable. It holds a place in pop culture that few man-made structures ever attain, most probably thanks to a giant fictional gorilla. In this black and white photograph, King Kong's exploits are still a couple of years off. The building is incomplete, its dirigible dock is still under construction.

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Flatiron Building After a Snowstorm, 1906

Flatiron Building After a Snowstorm, 1906

A cold winter morning in 1906. The Flatiron building rises up beyond the barren trees and the silhouttes of intrepid New Yorkers out walking. No streetcars can be seen. Only the legs of people and horses seem able to traverse the snow covered streets outside Madison Square Park.

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Madison Square Park, 1902

Madison Square Park, 1902

New Yorkers love their greenspaces. In this black and white photograph from 1902, we see a mother and her children strolling through Madison Square Park. Fellow New Yorkers occupy the benches, chatting, and reading newspapers. Beyond the cool shade of the trees, looms the newly-constructed Flatiron Building, an urban icon seen from a bucolic setting.

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Flatiron Building Seen from 26th Street, 1907

Flatiron Building Seen from 26th Street, 1907

The Flatiron District doesn't look terribly different today, with the iconic Flatiron Building cutting like a ship's prow through the combined traffic of Fifth Avenue and Broadway. It's the nature of the traffic that's changed. Here we see horses, carriages, and streetcars, rather than the cars, taxis, and buses of today. Oh, and maybe there are a few more tall buildings. But really, with the Flatiron in view, who notices them?

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View South from the Metropolitan Life Insurance Company Tower, 1912

View South from the Metropolitan Life Insurance Company Tower, 1912

In this hand-colored photograph, taken in 1912 by Irving Underhill, we see a very different Lower Manhattan Skyline than we would today. In fact, Underhill was taking the picture from the tallest building in the world, the Metropolitan Life Insurance Company Tower. The Woolworth Building, which would take the title in 1913, was not yet completed. It can be seen at the vanishing point of the horizon. To its right is the Singer Building, which is now 1 Liberty Plaza, and a little further right, merely a speck in the harbor, is the Statue of Liberty.

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