Often regarded as the originator of the American short story, Irving produced a number of sketches of life in the Hudson River Valley of New York, and of life in England and Spain; these were popular enough that Irving is often said to be the first American author to earn a living solely from his writing. Like Nathaniel Hawthorne, Irving was acutely aware of America's cultural roots in Europe, and much of his work reflects both a nostalgia for and an updating of European life and folkways, as does the fact Irving spent a considerable portion of his adult life—over 20 years—living in Europe. Irving's "transitional" status is also evident in his powerful interest in American beginnings: a (largely comic) History of New York, a biography of Columbus (the literal "finder" of America, at least in popular myth), and a biography of George Washington (one of America's political "founders" and the man after whom Irving was named).

Many of Irving's tales have a supernaturalist element, though Irving's gentle humor and rationalist skepticism often hedge that supernaturalism considerably, especially in the American tales.