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.

Pennsylvania Station at Night, c. 1922

Pennsylvania Station at Night, c. 1922

What have we lost? Prior to the establishment of the Landmarks Commission, many wonderful buildings were torn down in the name of progress. Perhaps none was a greater loss than the original Penn Station. In this exterior night shot, it looks a worthy successor to the Roman monuments it was meant to evoke.

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Pennsylvania Station Restaurant, 1910

Pennsylvania Station Restaurant, 1910

In 1910, Pennsylvania Station was the paragon of New York elegance. This restaurant, populated by ghosts thanks to the photograph's long exposure, is a far cry from the fast food joints of today's Penn Station. Not only did one enter the city like a god, one was expected to eat like a human being.

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Aerial View of Midtown Spires, c. 1950

Aerial View of Midtown Spires, c. 1950

In this aerial black and white photo from about 1950, we see the spires of Midtown East, including the Helmsley Building and the Chrysler Building. The midcentury haze obscures southern manhattan and Queen, giving the sense that the world beyond Midtown Manhattan ceases to to exist.

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Metropolitan Life Tower Under Construction, 1909

Metropolitan Life Tower Under Construction, 1909

In this black and white photograph from 1909, we see a group of men and ladies with parasols standing in Madison Square Park, observing the construction of the Metropolitan Life Tower. The main building had been constructed over a decade and half before.  The architectural firm of Napoleon LeBrun & Sons modeled the tower after the Campanile in Venice, Italy. It was the world's tallest building for three years, until 1913, when it was surpassed by the Woolworth Building.

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The Flatiron Building after a Snow Storm, 1906

The Flatiron Building after a Snow Storm, 1906

In this view south from East 26th Street and Fifth Avenue, the Flatiron Building looks like it is plowing through the snow. It looks like a substantial amount of fresh snow has blanketed the city, all of which has been shoveled by hand. The streets are as clear as they are likely to get until the hooves of the horses tramp it into slush. But luckily for us, some anonymous photographer captured the clean beauty of this moment forever.

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Metropolitan Museum of Art, 1909

Metropolitan Museum of Art, 1909
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Aerial Overview of the Empire State Building, 1964

Aerial Overview of the Empire State Building, 1964

The Empire State Building is no less impressive when seen from above than from below. In this aerial photograph, taken in 1964, we can see the Art Deco masterpiece in all its glory. It dominates the midtown skyline, stabbing upward into the sky, defiantly daring someone to build a taller building. It would be nearly a decade before anyone would.

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Wall and Broad Streets, 1916

Wall and Broad Streets, 1916

Ah, Wall Street. You can almost smell the money -- unless, like the gentleman in the extreme foreground, you have your finger jammed up your nose. On this day in 1916, the photographer captured the bustling activity of New York City's Financial District. Looking west along Wall, on the right you can see Federal Hall, which at the time was the United States Sub-Treasury building, on the left sit the newly-built House of Morgan and the New York Stock Exchange, and straight ahead, beyond Broadway is Trinity Church.

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Lower Manhattan Skyline looking North, 1930

Lower Manhattan Skyline looking North, 1930

A man in silhouette looks out from a high office in City Bank-Farmers' Trust Company Building toward 40 Wall Street, then known at the Bank of Manhattan Trust Building, which had only recently passed the Woolworth Building, visible further uptown, as the tallest building in the world. 40 Wall held that title for only a few weeks before being surpassed by the Chrysler Building, which can be seen through the window to the extreme right.

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