Bailey's special subject were city streets, landscapes, buildings and maritime scenes in Europe and America. The best known of his drawings are his sketches in pencil of London, his watercolor and drawings of Spain and his drawings of skyscrapers in New York City. Bailey was the first artist privileged by the United States government on the declaration of war to make drawings of navy yards, munition factories, and other centres of war work, as mentioned. These drawings appeared in exhibitions and were published in the leading magazines throughout the country. The collections he created in Spain were later bought by The Hispanic Society, and were shown in the Musée de la Guerre of France contains a collection of lithographs of American war subjects. Besides his work as a newspaper artist in London and America, Bailey illustrated many books.
