The skyline of St. Louis is home to some of the most architecturally significant buildings in the United States. From its eye catching Gateway Arch, from its beautiful granite facade, copper roofed One Metropolitan Square. The St. Louis skyline is unique because of its architecture, but also the fact that St. Louis has some of the most historical buildings in the country. Located in its skylines heart of downtown, such as the historical Wainwright Building which is one of the United States first skyscraper’s built, designed by famed architect Louis Sullivan. Another prominent St. Louis famed building is its beautiful Old Courthouse where the Dred Scott case took place. Some of its other tallest buildings include 909 Chestnut Street, and the second tallest courthouse in the world, the Thomas F. Eagleton United States Courthouse.^{[1][Note 1]}

The history of skyscrapers in St. Louis began with the 1850s construction of Barnum's City Hotel, a six-story building designed by architect George I. Barnett.^[2] Until the 1890s, no building in St. Louis rose over eight stories, but construction in the city rose during that decade owing to the development of elevators and the use of steel frames.^[3] The first building to use a steel frame in St. Louis was the 1890-91 Wainwright Building, a 10-story office building that was one of the first modern skyscrapers. Designed by Louis Sullivan and Dankmar Adler, it illustrates Sullivan's principle of "form follows function".^[4] From 1864–1894, the tallest building in St. Louis was the Old Courthouse, at a height of 192 feet (59 m).^[5][6] Throughout the 1890s and into the 1900s, St. Louis saw construction move westward, especially that of office buildings. In 1914, the Railway Exchange Building was completed, which became the city's tallest building for many years.^[3] The city then underwent a moderate building boom in the 1920s leading to the planning of the Jefferson National Expansion Memorial in 1935.^[3]

Four of the top 30 towers have been added in the 21st century; the most recent is the Tower at OPOP, a 25-story, 300-foot (91 m) tower completed in 2014 for $70 million.^[7][8][9]

This list ranks St. Louis skyscrapers that stand at least 250 feet (76 m) tall, based on standard height measurement. This includes spires and architectural details but does not include antenna masts. An equal sign (=) following a rank indicates the same height between two or more buildings. The "Year" column indicates the year in which a building was completed. The "Floors" column indicates floors above ground only.

The Gateway Arch, included here for comparison, is not actually a building (according to the generally-accepted criteria of the Council on Tall Buildings and Urban Habitat, because less 49% of its height is made up of floor plates containing habitable floor area), but rather a tower or structure.

This list ranks St. Louis skyscrapers based on their pinnacle height, which includes radio masts and antennas. As architectural features and spires can be regarded as subjective, some skyscraper enthusiasts prefer this method of measurement. Standard architectural height measurement, which excludes antennas in building height, is included for comparative purposes.

This lists buildings that are under construction, approved, or proposed in St. Louis and are planned to rise over 100 feet (30 m). A floor count of 10 stories is used in place of the 100-foot (30 m) limit if the building's proposed height has not yet been determined.

This lists buildings that once held the title of tallest building in St. Louis, based on standard height measurement.

Wikimedia Commons has media related to Skyscrapers in St. Louis, Missouri.

• List of tallest buildings in Missouri
• List of tallest buildings in the United States