Not only a Manhattan icon, the Flatiron Building has become an architectural landmark since its construction in 1902. Designed by the Chicago architect Daniel Burnham, it was among the first skyscrapers in the city and stood as the tallest building north of 14th Street. Shortly after its completion, the building’s architecture became a catalyst for swirling downdrafts, enticing opportunistic guys seeking a glimpse of girl’s skirts blowing in the wind. To mitigate this problem, policemen would yell “23 skidoo” to disperse the loitering young men, which unwittingly launched the American catchphrase. Though New York would go on to challenge the skies many more times, this was one of the first structures that demonstrated the sky as the limit itself.

Though New York would go on to challenge the skies many more times, this was one of the first structures that demonstrated the sky as the limit itself and as one of the oldest surviving skyscrapers in New York it remains famous for its Renaissance palazzo-inspired design.