Skyscraper Photos of Historic Buildings

Detail of the red terra cotta facade of the Wainwright State Office Building in St. Louis, Missouri
Wainwright State Office Building in St. Louis, Missouri. Raymond Boyd/Getty Images

Something about a skyscraper inspires awe and wonder. The skyscrapers in this photo gallery aren't necessarily the world's tallest, but they rank high for the beauty and ingenuity of their design. Explore the history of high-rises from the 1800s and the Chicago School. Here are photos of the Home Insurance Building, which many consider to be the first skyscraper, and the Wainwright, which became a prototype for high-rise office building design. Books about skyscrapers will often include photos of these historic skyscrapers:

The Home Insurance Building

Black and white photo of 19th century high-rise office building
Considered the First American Skyscraper, the Home Insurance Building Built in 1885 by William LeBaron Jenney. Bettmann/Getty Images (cropped)

After the Great Chicago Fire of 1871 destroyed much of the city's wooden buildings, William LeBaron Jenney designed a more fire-resistant structure framed with interior steel. At the Corner of Adams and LaSalle Streets in Chicago, Illinois, stood the 1885 prototype for buildings yet to be built. Reaching a height of 138 feet (expanded to 180 feet in 1890), the Home Insurance Building was a full 10 stories high, with two more stories added in 1890.

Until the mid-1800s, tall buildings and towers were structurally supported by thick, stone or earthen walls. William LeBaron Jenney, an engineer and urban planner, used a new metal material, steel, to create a stronger, lighter framework. Steel beams would support a building's height, on which the "skin" or exterior walls, like cast-iron facades, could hang or be attached. Earlier cast-iron buildings, such as the shorter 1857 Haughwout Building in New York City, used a similar frame construction technique, but cast-iron is no match to steel in terms of strength. Steel framing allowed buildings to rise and "scrape the sky."

The Home Insurance Building, demolished in 1931, is considered by many historians to be the very first skyscraper, even though architects' plans for using the steel cage building technique were all over Chicago at the time. Jenney has been called "Father of the American Skyscraper" not only for completing this building first among the Chicago School architects, but also for mentoring important designers such as Daniel Burnham, William Holabird, and Louis Sullivan.

The Wainwright Building

The Wainwright Building in St. Louis, Missouri.
Louis Sullivan's Form and Function The Wainwright Building in St. Louis, Missouri. Raymond Boyd/Getty Images

Designed by Louis Sullivan and Dankmar Adler, the Wainwright Building, named after Missouri brewer Ellis Wainwright, became a prototype for designing (not engineering) the modern day office buildings. To empathize the height, architect Louis Sullivan used a three-part composition:

  • The first two stories are unornamented brown sandstone with large, deep windows.
  • The next seven stories are uninterrupted red brick. Between the piers are horizontal panels decorated with leaf ornamentation.
  • The top story is decorated with round windows and terra cotta leaf scroll ornaments inspired by the Notre-Dame de Reims in France.

Louis Sullivan wrote that the skyscraper "must be tall, every inch of it tall. The force and power of altitude must be in it the glory and pride of exaltation must be in it. It must be every inch a proud and soaring thing, rising in sheer exultation that from bottom to top it is a unit without a single dissenting line." (The Tall Office Building Artistically Considered, 1896, by Louis Sullivan)

In his essay The Tyranny of the Skyscraper, architect Frank Lloyd Wright, an apprentice to Sullivan, called the Wainwright Building "the very first human expression of a tall steel office-building as Architecture."

The Wainwright Building, constructed between 1890 and 1891, still stands at 709 Chestnut Street in St. Louis, Missouri. At 147 feet (44.81 meters) tall, the Wainwright's 10 stories are more significant in architectural history than a skyscraper 10 times this height. This early skyscraper has been called one of the ten buildings that changed America.

The Meaning of "form ever follows function"

" All things in nature have a shape, that is to say, a form, an outward semblance, that tells us what they are, that distinguishes them from ourselves and from each other....the lower one or two stories will take on a special character suited to the special needs, that the tiers of typical offices, having the same unchanging function, shall continue in the same unchanging form, and that as to the attic, specific and conclusive as it is in its very nature, its function shall equally be so in force, in significance, in continuity, in conclusiveness of outward expression...." — 1896, Louis Sullivan, The Tall Office Building Artistically Considered

The Manhattan Building

Early skyscrapers today called high-rises in Chicago including Jenney's Manhattan
East side of South Dearborn Street in Chicago, Historic Skyscrapers Including Jenney's Manhattan. Payton Chung on, Creative Commons Attribution 2.0 Generic (CC BY 2.0)

The late 19th Century building boom created a race to the top for developers, architects, and engineers. William LeBaron Jenney was no exception. Located at 431 Dearborn Street, this 1891 Chicago landmark, at only 170 feet high and 16 stories, has been called the oldest surviving skyscraper in the world.

The lower floor cast-iron exterior facade does not hold the building's weight. Like other Chicago School high-rises, the interior steel framework allowed the building's height to soar and the exterior to be a skin of windows. Compare with Jenney's earlier 1885 Home Insurance Building.

Leiter II Building

Photo of massive, high-rise building in Chicago, 1970s, with a SEARS sign on the side
Further Development of Steel Frame Construction, Second Building Built for Levi Z. Leiter by William LeBaron Jenney, 1891. Hedrich Blessing Collection/Chicago History Museum/Getty Images (cropped)

Also known as the Second Leiter Building, the Sears Building, and the Sears, Roebuck & Company Building, Leiter II was the second department store built for Levi Z. Leiter by William LeBaron Jenney in Chicago. It stands at 403 South State and East Congress Streets, Chicago, Illinois.

About the Leiter Buildings

The first department store Jenney built for Levi Z. Leiter was in 1879. Leiter I Building at 200-208 West Monroe Street in Chicago has been cited as a Chicago Architectural Landmark for its "contribution towards the development of skeleton construction." Jenney experimented with using cast iron pilasters and columns before the realization of cast-iron's brittleness. The First Leiter Building was brought down in 1981.

Leiter I had been a conventional box supported by iron columns and exterior masonry piers. For his second Leiter Building in 1891, Jenney used iron supports and steel beams to open the interior walls. His innovations made it possible for masonry buildings to have larger windows. Architects of the Chicago School experimented with many designs.

Jenney found success with a steel skeleton for the 1885 Home Insurance Building. He built on his own success for Leiter II. "When the second Leiter Building was built," says the U.S. Historic American Buildings Survey, "it was one of the largest commercial structures in the world. Jenney, the architect, had solved the technical problems of skeleton construction in the first Leiter Building and the Home Insurance Building; he revealed in the second Leiter Building an understanding of its formal expression - his design is clear, confident and distinctive."

The Flatiron Building

tall, thin, masonry high rise building, ornate, behind the branches of a tree
New York's Wedge-Shaped Skyscraper The Flatiron Building in New York City. Andrea Sperling/Getty Image

The 1903 Flatiron Building in New York City is one of the world's earliest skyscrapers.

Although officially named the Fuller Building, Daniel Burnham's innovative skyscraper quickly became known as the Flatiron Building because it was wedge-shaped like a clothing iron. Burnham gave the building this unusual shape to maximize use of the triangular lot at 175 Fifth Avenue near Madison Square Park. The Flatiron Building at 285 feet (87 meters) high is only six feet wide at its tip. Offices at the narrow point of the 22 story building offer spectacular views of the Empire State Building.

When it was constructed, some people worried that the Flatiron Building would collapse. They called it Burnham's Folly. But the Flatiron Building was actually a feat of engineering that used newly developed construction methods. A sturdy steel skeleton allowed the Flatiron Building to achieve record-breaking height without the need for wide supporting walls at the foundation.

The limestone facade of the Flatiron building is decorated with Greek faces, terra cotta flowers, and other Beaux-Arts flourishes. The original double hung windows had wooden sashes that were clad in copper. In 2006, a controversial restoration project altered this feature of the landmark building. The curved windows at the corners were restored, but the rest of the windows were replaced using insulated glass and aluminum frames painted with a copper-colored finish.

The Woolworth Building

Low angle view of Gothic Revival Woolworth building in Lower Manhattan
Looking Up at Cass Gilbert's Gothic Revival 1913 Woolworth Building in New York City. In Pictures Ltd./Corbis via Getty Images

Architect Cass Gilbert spent two years, drawing thirty different proposals, for the office building commissioned by Frank W. Woolworth, owner of the dime store chain. On the outside the Woolworth Building had the look of a Gothic cathedral from the Middle Ages. With a memorable grand opening on April 24, 1913, the Woolworth Building at 233 Broadway in New York City can be called Gothic Revival. On the inside, however, it was a 20th century modern commercial building, with steel framing, elevators, and even a swimming pool. The structure was quickly dubbed "The Cathedral of Commerce." Soaring 792 feet (241 meters) high, the Neo-Gothic skyscraper was the world's tallest building until the Chrysler Building was erected in 1929.

Gothic-inspired details adorn the cream-colored terra cotta facade, including gargoyles, which caricatured Gilbert, Woolworth, and other famous people. The ornate lobby is lavished with marble, bronze, and mosaics. Modern technology included high-speed elevators with air cushions that would stop a car from falling. Its steel framework, built to endure the high winds of Lower Manhattan, withstood everything when terror struck the city on 9/11/01 — all 57 stories of the 1913 Woolworth Building stand a mere block from Ground Zero.

Because ofthe building's eery presence after the attacks, some people believe that missiles were launched from its roof toward the Twin Towers. By 2016, a new set of believers can keep watch over New York's Financial District from the newly remodeled upper floor condos.

What would the architect think? Probably the same thing he reportedly said back then: " is after all only a skyscraper."

Chicago Tribune Tower

the Tribune Tower in Chicago is Neo-Gothic in design
The Chicago Tribune Building, 1924, by Raymond Hood and John Howells. Jon Arnold/Getty Images

Architects of the Chicago Tribune Tower borrowed details from medieval Gothic architecture. Architects Raymond Hood and John Mead Howells were selected over many other architects to design the Chicago Tribune Tower. Their Neo-Gothic design may have appealed to the judges because it reflected a conservative (some critics said "regressive") approach. The facade of the Tribune Tower is studded with rocks collected from great buildings around the world.

The Chicago Tribune Tower at 435 North Michigan Avenue in Chicago, Illinois was built between 1923 and 1925. Its 36 stories stand at 462 feet (141 meters).

The Chrysler Building

Night aerial view of the top of the Art Deco Chrysler Building in New York City has jazzy automobile ornaments
The Art Deco Chrysler Building in New York City has jazzy automobile ornaments. Alex Trautwig/Getty Images

The Chrysler Building at 405 Lexington Avenue, easily seen in New York City from Grand Central Station and the United Nations, was completed in 1930. For a few months, this Art Deco skyscraper was the tallest structure in the world. It was also one of the first buildings composed of stainless steel over a large exposed surface. Architect William Van Alen ornamented the Chrysler Building with jazzy automobile parts and symbols. At a height of 1,047 feet (319 meters), this iconic, historic 77 story skyscraper remains in the top 100 tallest buildings in the world.

GE Building (30 Rock)

Looking up at the art deco 1933 skyscraper at Rockefeller Center
The Art Deco RCA Building, a 1933 Skyscraper by Raymond Hood, Viewed from Rockefeller Plaza. Robert Alexander/Getty Images (cropped)

Architect Raymond Hood's design for the RCA Building, also known as the GE Building at 30 Rockefeller Center, is the center of the Rockefeller Center Plaza in New York City. At a tiered height of 850 feet (259 meters), the 1933 skyscrapers is popularly known as 30 Rock.

The 70 story GE Building (1933) at Rockefeller Center is not the same as the General Electric Building on 570 Lexington Avenue in New York City. Both are art deco designs, but the 50-story, General Electric Building (1931) designed by Cross & Cross is not part of the Rockefeller Center complex.

Seagram Building

two people sitting near a pool in front of a skyscraper set back from the streets of New York City
The Seagram Building in New York City. Matthew Peyton/Getty Images (cropped)

Constructed between 1954 and 1958 and built with travertine, marble, and 1,500 tons of bronze, the Seagram Building was the most expensive skyscraper of its time.

Phyllis Lambert, daughter of Seagram founder Samuel Bronfman, was tasked with finding an architect to build what has become an iconic modern skyscraper. With help from architect Philip Johnson, Lambert settled on a well-known German architect, who, like Johnson, was building in glass. Ludwig Mies van der Rohe was building the Farnsworth House and Philip Johnson was constructing his own glass house in Connecticut. Together, they created a skyscraper of bronze and glass.

Mies believed that a skyscraper's structure, its "skin and bones," should be visible, so the architects used decorative bronze beams to accentuate the structure at 375 Park Avenue and to emphasize its height of 525 feet (160 meters). At the base of the 38 story Seagram Building is a two-story high glass-enclosed lobby. The entire building is set back 100 feet from the street, creating the "new" concept of the city plaza. The open urban space allows office workers an outdoor focus and also permits the architect to design a new style of skyscraper — a building without setbacks, which allows sunlight to reach the streets. This aspect of the design is in part why the Seagram Building has been called one of ten buildings that changed America.

The book Building Seagram (Yale University Press, 2013) is Phyllis Lambert's personal and professional recollections of the birth of a building that influenced both architecture and urban design.

John Hancock Tower

Glass facade skyscraper, the John Hancock Tower in Boston
Pei, Cobb, & Freed in Boston John Hancock Tower in Boston. Steven Errico/Getty Images

The John Hancock Tower, or The Hancock, is a 60-story modernist skyscraper set in Boston's 19th century Copley Square neighborhood. Built between 1972 and 1976,  the 60 story Hancock Tower was the work of architect Henry N. Cobb of Pei Cobb Freed & Partners. Many Boston residents complained that the skyscraper was too flamboyant, too abstract, and just too high-tech for the neighborhood. They worried that the Hancock Tower would overshadow nearby nineteenth-century masonry Trinity Church and Boston Public Library.

However, after the John Hancock Tower was completed, it was widely praised as one of the most beautiful parts of the Boston skyline. In 1977, Cobb, a founding partner in I.M. Pei's firm, accepted an AIA National Honor Award for the project.

Famed as the tallest building in New England, the 790-foot-tall (241 meter) John Hancock Tower is perhaps even more famous for another reason. Because the technology for a building covered with this kind of all-glass façade had not yet been perfected, windows began falling by the dozens before construction was complete. Once this major design flaw was analyzed and fixed, each of the more than 10,000 panes of glass had to be replaced. Now the Tower's smooth curtain of glass reflects nearby buildings with little or no distortion. I. M. Pei later used the corrected technique when he built the Louvre Pyramid.

Williams Tower (Formerly the Transco Tower)

Detail of the glass facade of the Williams Tower in Houston, Texas
The 1983 Williams Tower (Formerly the Transco Tower) in Houston, Texas. James Leynse/Corbis via Getty Images (cropped)

Williams Tower is a glass and steel skyscraper located in the Uptown District of Houston, Texas. Designed by Philip Johnson with John Burgee, the former Transco Tower has the glass and steel rigor of the International Style in a softer Art Deco-inspired design.

At a height of 901 feet (275 meters) and 64 floors, Williams Tower is the taller of two Houston skyscrapers completed by Johnson and Burgee in 1983.

Bank of America Center

Stepped top of the Gothic-inspired yet postmodern dark red granit skyscraper once called the Republic Center
Bank of America Center, 1983, in Houston, Texas. Nathan Benn/Corbis via Getty Images (cropped)

Once called the Republic Bank Center, the Bank of America Center is a steel skyscraper with a distinct red granite facade in Houston, Texas. Designed by Philip Johnson with John Burgee, it was completed in 1983 and built at the same time the architects' Transco Tower was being completed. At a height of 780 feet (238 meters) and 56 floors, the Center is smaller, in part because it it built around an existing two-story building.

AT&T Headquarters (SONY Building)

Chippendale top of skyscraper designed by Philip Johnson
Philip Johnson's Playful Top of AT&T Headquarters now SONY in New York City. Barry Winiker/Getty Images

Philip Johnson and John Burgee headed to 550 Madison Avenue in New York City to erect one of the most iconic skyscrapers ever built. Philip Johnson's design for the AT&T Headquarters (now the Sony Building) was the most controversial of his career. At street level, the1984 building appears to be a sleek skyscraper in the Interntional Style. However, the peak of the skyscraper, at a height of 647 feet (197 meters), is adorned with a broken pediment that was scornfully compared to the ornamental top of a Chippendale desk. Today, the 37 story skyscraper is often cited as a masterpiece of Postmodernism.


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Craven, Jackie. "Skyscraper Photos of Historic Buildings." ThoughtCo, Apr. 5, 2023, Craven, Jackie. (2023, April 5). Skyscraper Photos of Historic Buildings. Retrieved from Craven, Jackie. "Skyscraper Photos of Historic Buildings." ThoughtCo. (accessed June 10, 2023).