The world's tallest building upon completion in 1913 (it was only surpassed in height by the Chrysler Building in 1930), Cass Gilbert’s 60-story, 792ft-tall Woolworth Building is a neo-Gothic marvel, elegantly clad in masonry and terra-cotta. The breathtaking lobby – a spectacle of dazzling, Byzantine-like mosaics – is accessible only on prebooked guided tours, which also offer insight into the building's more curious original features, among them a dedicated subway entrance and a secret swimming pool.
At its dedication, the building was described as a ‘cathedral of commerce’; though meant as an insult, FW Woolworth, head of the five-and-dime chain-store empire headquartered there, took the comment as a compliment and began throwing the term around himself. Today, it's more like a cathedral of condos, as the top 30 floors have been converted to ultraluxury residences, including a 'Pinnacle Penthouse' that takes up the top seven floors and includes an open-air observatory.