The world’s best-known cities are home to iconic skylines: think the staggered skyscrapers of New York, the eclectic architecture of Chicago and the shiny towers of Shanghai. But while many of these cityscapes are seared into our memories, they haven’t always looked that way. Some have evolved over time, with a tower erected here, a building demolished there – while others seem to have sprung up almost overnight. Here are some incredible archive images and illustrations that show how city skylines have transformed through the years, decades and centuries.

Few cities are so synonymous with architectural brilliance as Chicago. The Windy City is, after all, the birthplace of the skyscraper. The world’s first, the Home Insurance Building, was completed in 1885 and rose to 138 feet (42m) and 10 stories – not exactly lofty by today’s soaringly high standards, but a game changer at the time. It was constructed with a steel frame that supported its weight, but with a brick exterior, a technique that became known as the “Chicago Skeleton”. This image, taken in 1911, shows the skyline starting to take shape along the shores of Lake Michigan.

Sadly, the landmark building was demolished in 1931, making way for the Field Building (now the Lasalle Bank Building), and the skyline began to take on a somewhat steelier style. By 1980 (pictured), many of the city’s most iconic structures had taken their place. The Willis Tower, rising above the others (left), was completed in 1974, as was the Aon Center, the white rectangular structure that dominates the skyline left of center. Older buildings, including the 1924 Wrigley Building with its Seville-inspired clock tower, were already getting a little lost.

Today, while it isn’t home to the world’s tallest buildings, Chicago has a beautiful mix of architectural styles. And the skyline remains dynamic, with several towers over 800 feet (244m) currently under construction and others yet to break ground. New additions already to appear along the lakeshore include One Bennett Park (far right), opened in 2019, and NEMA Chicago by Grant Park. Willis Tower is still the city’s tallest structure at 1,450 feet (442m) – edging Trump Tower, built in 2005 and seen here in the center, by 62 feet (19m).

Sydney’s waterfront was once relatively nondescript and almost unrecognizable from how it looks today, as this image of the harbor shows. Taken circa 1870–1880, this picture shows Circular Quay when it functioned as a working port, with a largely undeveloped shoreline lined with ships and boats of various sizes.

By 1955, one of the skyline’s most recognizable landmarks had curved over the water for 23 years. The Sydney Harbour Bridge was finished in 1932 with a span of 1,650 feet (500m), putting it among the world’s longest steel-arch bridges. It took eight years to complete, its two sides built into each bank, and came to symbolize the city – as well as marking the harbor out as a tourist attraction.

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There was still a significant structure missing, though. Sydney’s most iconic building, the Opera House, opened in 1973 and changed the skyline forever. Its unique architecture, with a gleaming sail-like shape that’s often illuminated after dark, is instantly recognizable. Many other now-famous structures also popped up along the downtown skyline in the latter half of the 20th century, including the spindly Sydney Tower Eye.

In 1993, this JVC Electronics tower is one of the most dominant buildings in Kuala Lumpur. The city underwent a building boom from the 1970s and, by that time, was on the cusp of huge architectural change. In the distance is a smattering of hotels, banks and office blocks, interspersed with construction sites. But the biggest and arguably the best was yet to come.

One thing has totally transformed the skyline since. Actually, two things: the Petronas Towers, opened in 1996. They’re officially the tallest twin towers in the world, soaring in synchronicity to nearly 1,483 feet (452m). Other additions from the late 20th century onwards include the Kuala Lumpur or KL Tower, topped with an antenna, and the Istana Budaya cultural center, bringing several different dimensions to the skyline in the style of Sydney Opera House.

Toronto’s skyline, beautifully defined on the northwestern shore of Lake Ontario, is a clear indication of how the city has changed. This engraving illustrates life on the harbor in around 1841, when it was a busy working port and quayside with fishing boats and was on the cusp of industrialization. Two fires – in 1849 and most devastatingly in 1904 – forced a new era of development and city planning.

The first half of the 20th century saw more buildings spring up along the waterfront, with the business district growing skywards. When the Canadian Bank of Commerce Tower was completed in the 1930s, it dominated the skyline as the tallest building not just in the city but in the entire British Commonwealth. The Royal York Hotel, to the left, was then the Commonwealth’s biggest hotel, too. Both structures remain, with the hotel now a Fairmont.

Now, of course, both of these structures have been dwarfed by a series of newer skyscrapers that have transformed the cityscape into a modern beauty. Overshadowing them all, though, is the Canadian National or CN Tower, the world’s tallest free-standing structure when it was completed in the 1970s (until Dubai’s Burj Khalifa came along, in 2009). Next to it – and beautifully illuminated – is the Rogers Centre or Toronto SkyDome, opened In 1989. But, given recent proposals for the dome's demolition, the skyline could change once again.

This etching, dating from around 1599, shows a long-lost London with medieval structures that have since been destroyed, torn down and/or replaced. Among the most prominent is the old St Paul’s Cathedral, which looms above other buildings and can be seen just left of center in this image, which looks at the skyline from Southwark. London Bridge, on the right, was then a mini-neighborhood with shops, homes and more elaborate structures. These included Nonsuch House, a Renaissance palace of carved wood made in Holland and added here in 1579.

Then came the catastrophic Great Fire of 1666, which destroyed around 80% of the city and changed the capital forever. A block of homes on London Bridge was destroyed and, while other buildings survived, they were removed by 1762 and the bridge was eventually demolished in 1832. Structures lost forever were the riverside Castle Baynard and the old Royal Exchange. Many were quickly rebuilt, and this image taken in 1802 from the relatively new Blackfriars Bridge shows the now familiar dome of St Paul’s Cathedral, with its fourth and still standing incarnation completed in 1710.

Today it’s a very different picture, as this recent shot from Waterloo Bridge demonstrates. St Paul’s is now the grande dame of the skyline and provides a stark contrast to skyscrapers including One Blackfriars on the South Bank (right) and, across the river, the city’s new tallest building: 22 Bishopsgate or Twentytwo. The gleaming towers of Canary Wharf, which has been a business district since the 1990s, can be spied in the distance.

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Hong Kong Harbour was renamed Victoria Harbour in the 1850s under British colonial rule. It's pictured here in around 1930, and you can see that its topography has changed, as well as the buildings along its shoreline. Land has been reclaimed from the natural harbor over the decades, altering its shape. Once a fishing village, the modern city grew from this area, backed by Victoria Peak – though by this stage the skyline was only just beginning to take shape.

Now it’s one of the world’s most famous cityscapes and among the most photographed waterfronts. Skyscrapers began springing up in the 1970s, each new structure seemingly vying to outdo its predecessors.  The first was the Connaught Centre, now Jardine House, in 1972, with its distinctive circular windows. Then came the 66-story, cylindrical Hopewell Centre in 1980, home to the city’s highest revolving restaurant and for a while the tallest structure of them all. That is until the International Commerce Centre, or ICC, came along in 2002, far surpassing it at 108 stories.

Dubai’s transformation has been both total and stunningly swift. From the 1960s, the relatively undeveloped and low-rise port city became a center for oil trading and the creek running through the city was a major route for ships. Infrastructure grew and high-rise buildings began to dominate the waterfront. By 1996, as shown in this photo, a few gleaming and gilded skyscrapers marked the beginning of a new era.

By the early 21st century, when this shot was captured, Dubai’s burgeoning skyline was fast developing with structures rivaling those in New York and Hong Kong. On the left are the Jumeirah Emirates Towers – built from 1996, they're almost identical, yet not quite. The tallest is an office block with 54 floors, while the other is a luxury, 400-room hotel.

Construction began on the Burj Khalifa, still the world’s tallest building at just over 2,716 feet (828m) tall, in 2004. This piercing addition to the skyline cemented Dubai’s reputation as a gleaming metropolis determined to be the biggest and best. Or, at the very least, the tallest. Other projects in the works include Dubai Creek Harbour, a complex that will include the Dubai Creek Tower, set to be the new tallest building (though work on the structure is currently paused).

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In 1864, when this image was captured across the San Francisco Bay, the former Spanish and later Mexican mission and pueblo was under US control, after it was captured in 1846 and renamed from Yerba Buena. Much of the city’s development began during the Gold Rush. The population increased from about 1,000 to 25,000 between 1948 and 1949: housing sprang up and life largely revolved around the port.

Today’s skyline couldn’t be more different. There’s the Bay Bridge – built in the 1930s along with its more famous near-neighbor, the Golden Gate – perfectly framing a now-sparkling skyline of towers and waterside life. The building boom began in the early 20th century after many of the city’s structures were destroyed in the 1906 earthquake and subsequent fires. Now, standout skyscrapers include the 2018-completed Salesforce Tower, the city’s tallest at 1,070 feet (326m), and the Transamerica Pyramid, completed in 1972 and standing at 853 feet (260m).

Frankfurt is Germany’s financial center and arguably home to its most distinctive skyline, with the vast majority of the country’s skyscrapers found here. This 1895 view from Sachsenhausen, on the opposite bank of the River Main, shows a dramatically different Frankfurt. Timber houses line the riverfront while, at this time, the tallest structure is the 312-foot (95m) Gothic tower of the Frankfurt Cathedral. Eiserner Steg, the iron footbridge that spans the river, was built in 1868.

Frankfurt looked like a different city by the late 20th century. The bridge is still there, as are many of the city’s historic structures, including the now relatively diminutive cathedral, smaller churches and the stepped gable façade of Frankfurter Römer, a medieval building that’s now the town hall. Yet, just beyond those, a strip of sky-piercing towers has risen up to add a shiny, modern layer to the old city. The Commerzbank Tower (center) became a symbol of the banking district. Completed in 1997, it was (and still is) the tallest building in Germany.

This futuristic strip has become more crowded over the past few decades as more skyscrapers and financial centers have joined the line-up and, in some cases, nudged other buildings out of the front row. Once dominant buildings such as the Deutsche Bank Twin Towers, just behind the cathedral, are almost dwarfed by new(ish)-comers like the cylindrical Main Tower, completed in 1999. Out of shot, to the east, are the twisted twin towers of the European Central Bank, completed in 2014.

Few cities have changed so dramatically and so swiftly as Shanghai – especially on the east bank of the Huangpu River. Most of the original development was on the western side of the water, which became a British settlement in the 1840s after Shanghai was occupied during the First Opium War. This early 20th-century photo shows some of the colonial-era buildings along the Bund promenade, many of which still stand today, and reveals just how undeveloped the other side remained until nearly a century later.

Now the east bank looks like aliens have taken over – or perhaps just some very ambitious architects. Shanghai’s futuristic Pudong district now boasts China’s tallest building (and the world’s second tallest, after Dubai’s Burj Khalifa): the 2,073-feet (632m) tall Shanghai Tower. Its twisty structure is just one of many unique shapes on the waterfront. There’s the Bottle Opener, as the World Financial Center is known, and the Oriental Pearl Tower, which looks like a spaceship ready for take-off.

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The vista across Rio from Corcovado to Sugarloaf Mountain is among the world’s most famous and inspiring. And, as this 1895 image shows, it’s always been gorgeous thanks to its beach-lined bays and views of forested peaks, islands and the Atlantic Ocean. At this point there was little to distract from the natural beauty of Guanabara Bay, with low-level homes, public buildings and churches barely bothering the sky. Rio was also the capital of independent Brazil from 1822 until Brasilia took the job in 1960.

By the 1960s, around 30 years after the iconic Christ the Redeemer statue was completed atop Corcovado, the same view was starting to look a little different. This picture was taken from the viewing platform near the statue. Several older buildings had been demolished and replaced by taller structures for housing, hotels and businesses, streets had been widened, some lagoons and swamps had been filled in and the port had been rebuilt in 1907.

Before the 1970s, the tallest structures were up to 30 stories high. Then came the skyscraper boom, which dramatically altered the view. Today the city’s center sprawls out before Christ the Redeemer as a patchwork of colonial-era, Neoclassical, modern and positively futuristic architecture. Among the most prominent structures is the 48-story Rio Sul Center Tower (right of the statue), the tallest in the city at 535 feet (163m) and completed in 1982.

New York, New York – so good they really did name it twice. The original Dutch settlement was known as New Amsterdam until 1674, when it was returned to the English and renamed in honor of the Duke of York, King James II. This 17th-century rendering illustrates just how different it Manhattan Island looked compared to the shiny tableau of skyscrapers and bridges that’s so familiar today. New Amsterdam, on the southern tip of Manhattan Island just below modern Wall Street, consisted of largely wooden buildings surrounded by farmland.

This early 20th-century image shows Lower Manhattan and Wall Street on the cusp of the skyscraper boom. The Singer Building (the darker shaded tower to the left) was the world’s tallest when it was erected in 1908, and was the tallest structure to be intentionally destroyed in 1966. In the foreground, the Battery, where artillery batteries once protected the early settlement, was already a popular green space. On the left, the International Mercantile Marine Company Building (formerly the Washington Building) was built in 1885 and remodeled in a Beaux-Arts style in 1921.

Over the decades, the Manhattan skyline evolved into one of the most famous and recognizable vistas in the world. Several iconic structures had added height to the city by the 1930s, with 30 Rockefeller Plaza, the Chrysler Building and the needle-topped Empire State Building all shooting up around this time. It was the Twin Towers of the World Trade Center, however, that most strikingly stood out in the jagged, gleaming cityscape. They’re shown here in 1976, three years after they were completed.

Today, of course, it’s their absence that stands out most starkly. This recent image shows One World Trade Center, erected on the site of the original World Trade Complex from 2006, as a symbol of the city’s resilience and spirit following the terrorist attacks of September 11, 2001. Elsewhere, a few remnants of New Amsterdam remain. Many area names, for example, stem from the Dutch, including Harlem, Coney Island and Brooklyn. The latter is also home to Wyckoff House, New York’s oldest building dating from 1652.

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