Born in San Francisco, he studied at the Mark Hopkins Art Institute for six months, started his career as an unpaid cartoonist for The San Francisco Examiner.[4] The Honolulu Advertiser was among the other newspapers art departments that he served in.[5] He also contributed to the San Francisco Evening Post. He also worked as an itinerant actor (for both stage and screen), newspaper illustrator, and piano player.[3] In 1906 he moved to the East Coast. In the 1910s he contributed many illustrations to both Red Book magazine and its sister publication, Green Book.[4]

Before World War I, Irvin contributed illustrations regularly to Life, and rose to the position of art editor. (Life the humorous weekly, and not to be confused with the more famous magazine of the same name published by Henry Luce). Irvin also contributed to Cosmopolitan when it was a serious literary publication. He illustrated Wallace Irwin's "Letters of a Japanese Schoolboy" in Life.[6] He would later incorporate Japanese imagery in satirical kakemono for The New Yorker.[6]

He also created a series of humorous advertisements for Murad (turkish tobacco cigarettes).[6]

He also contributed the illustrations for "Snoot If You Must," by Lucius Beebe, a noted raconteur of New York's cafe society (1943, D. Appleton-Century).

He was fired from his position as art editor at Life in 1924.

However, Irvin had joined an advisory board to help launch The New Yorker and then worked on the magazine's staff as an illustrator and art editor. When he had first taken the job, Irvin had assumed that the magazine would fold after a few issues,[4] but his work would ultimately appear on the cover of 169 issues of The New Yorker between 1925 and 1958.[7]

The magazine's first cover, of a dandy peering at a butterfly through a monocle, was drawn by Irvin; the dandy replaced at the last minute a drawing of theater curtains revealing the skyline of Manhattan.[3] The gentleman on the original cover is referred to as "Eustace Tilley," a character created for The New Yorker by Corey Ford. Another example is the piece known as The Unity of the Allied Nations, which appeared on the cover of the July 1, 1944 issue, and depicts the national personifications of the Allies (the American Eagle, the Chinese Dragon, the Russian Bear and the British Lion).[7]

Besides covers for the magazine, Irvin also drew various illustrations, department headings, caricatures, and cartoons.[3]

The New Yorker signature display typeface, used for its nameplate and headlines and the masthead above The Talk of the Town section, is called "Irvin" or "Irvin type," after him.[8] An alphabet drawn by the American etcher Allen Lewis, who had received training in woodcutting in Paris, was used as the typographical basis for the "Irvin type."[3] Irvin may have spotted Lewis' lettering, which was drawn to imitate a woodcut, in a pamphlet entitled "Journeys To Bagdad", and liked it so much that Irvin asked Lewis to create the entire alphabet.[3] Uninterested in this project, Lewis suggested that Irvin create the alphabet himself –this became the "Irvin type."[3]