The youngest of 11 children, Irving was indulged by his parents. His first satirical essays were published when he was only 19. He did not attend college but read for the law and passed the bar examination in 1806. Rather than practice law, he continued writing essays and satires.

His lifelong interest in writing was periodically interrupted by various business and diplomatic ventures. In 1811 he moved to Washington to lobby on behalf of his family’s importing business. In 1815 he moved to London, again on behalf of family business. While in England he wrote "The Sketch Book of Geoffrey Crayon" (1819-1820) that contained the short stories that would become famous. He traveled extensively in Europe and served in various diplomatic posts, including four years (1842-1846) as US ambassador to Spain. He spent the latter part of his life at his estate in New York, writing history and biography, including a five-volume biography of George Washington.