Located in Manhattan at 175 Fifth Avenue and Broadway, the Flatiron Building is a groundbreaking skyscraper. Built in 1902, it encompasses 22 stories and 307 feet. While not the tallest skyscaper in New York, it’s dramatic Beaux-Arts facade makes it a popular attraction, especially with photographers. What also makes it unusual is, unlike other early skyscrapers in New York that looked like rising towers, the Flatiron building showcases a concept from the Chicago school that divides the facade into a base, shaft and capital, which makes sense as it was designed by Chicago architect Daniel Burnham. The name of building stems from its resemblance to a cast-iron clothing iron. Interestingly, back then the building’s unique shape was thought to create intense updrafts that would lift women’s skirts passing on 23rd Street. If a man tried to sneak a peak, police should shout “Hey! 23 skidoo!” This is thought to be where the phrase comes from. The Flatiron Building is so iconic, the neighborhood, Flatiron, was named after it, and now attracts design buffs and creative consumers looking to browse its art and design-related shops. Don’t forget to take in the skyline from behind the adjacent Madison Square Park, as it’s one of the most beautiful viewpoints in the city.