Built in 1902, the 20-story Flatiron Building, designed by Daniel Burnham, has a uniquely narrow triangular footprint that resembles the prow of a massive ship, and a traditional beaux arts limestone facade, built over a steel frame, that gets more complex and beautiful the longer you stare at it. Best viewed from the traffic island north of 23rd St between Broadway and Fifth Ave, this unique structure dominated the plaza back in the skyscraper era of the early 1900s. In fact, until 1909 it was the world’s tallest building.

The construction of the Flatiron building (originally known as the Fuller Building) coincided with the proliferation of mass-produced picture postcards – the partnership was kismet. Even before its completion, there were images of the soon-to-be tallest tower circulating the globe, creating much wonder and excitement.

Publisher Frank Munsey was one of the building’s first tenants, and from his 18th-floor offices, published Munsey’s Magazine, which featured the writings of short-story writer William Sydney Porter, whose pen name was ‘O Henry’. His musings (in popular stories such as ‘The Gift of the Magi’), the paintings of John Sloan and photographs of Alfred Stieglitz, best immortalized the Flatiron back in the day – along with a famous comment by actress Katherine Hepburn, who said in an interview that she’d like to be admired as much as the grand old building.

Like many of New York City’s monumental homages to civic progress, the Flatiron building is still fully functional and houses an assortment of private businesses. The famed structure is therefore best appreciated from the exterior. Plans are underway to transform the building into a luxurious five-star hotel, but progress is on permanent hold until the final tenants willingly vacate the premises.