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A striking triangular sliver, this Ladies’ Mile landmark fans outwards from 23rd to 22nd Sts., with its rounded, prow-like front measuring only six feet across. At its completion in 1902, architect D.H. Burnham's 22-story skyscraper dwarfed its neighbors and elicited an immediate controversy. One critic even compared it to “a stingy piece of pie.” Skeptics vowed it would never withstand the notoriously windy corner where Fifth Ave. and Broadway cross paths. In the end, the 3,680-ton steel structure—one of the earliest of its kind—proved them wrong and its success became a catalyst for further development and uptown expansion. Though the Flatiron's restaurant and the observation deck are long closed to the public, visitors can still duck into the small lobby for the series of historic photographs and background notes hanging from one wall. The building was always intended for office space and is currently the headquarters of St. Martin’s Press. A handful of stores occupy the street level. Named after the Fuller Construction Company, the “Fuller Building” quickly took on the Flatiron moniker, a nod to the building’s resemblance to an old-fashioned flat iron. Lion heads, Greek faces, fleur de lis and enveloping geometric designs adorn the terra cotta exterior, which recalls an Italian Renaissance palazzo. Once the most photographed building in New York, the Flatiron has been captured by Alfred Stieglitz, Edward Steichen, and countless tourists. — Kate Appleton