Ernest Howard Shepard was born in London to Henry and Jessie Shepard. Ernest’s father was an architect from a highly respected family, and his mother was the daughter of distinguished watercolorist, William Lee. Ernest attended school at St. Paul’s where he was enrolled in an advanced drawing class. Like Gordon Browne, Ernest took additional art classes on Saturdays at Heatherley’s art school in London. Though Ernest envisioned a more adventurous life for himself, he pursued a career in art by winning a scholarship to the Royal Academy Schools.
Shepard turned his full focus to illustration and submitted ideas to Punch two or three times a week until they accepted two of his drawings in 1907. Since graduating art school, Shepard worked as a book illustrator on publications such as Tom Brown’s Schooldays by Thomas Hughes, David Copperfield by Charles Dickens, Henry Esmond by W.M. Thackeray, Aesop’s Fables, and Smouldering Fires by Evelyn Everett-Green.
In 1924, Shepard was invited to illustrate the book When We Were Very Young by A.A. Milne. In 1925, Milne purchased Cotchford Farm in Sussex as a country home for he and his family. The house was surrounded by meadows and woods that would inspire the following books about the adventures of Winnie-the-Pooh and Christopher Robin. In order to follow Milne’s clear instructions for the illustrations, Shepard travelled to his country house to observe the area. Winnie-the-Pooh was published in 1926.
By 1931, Kenneth Grahame invited Shepard to illustrate his children’s classic The Wind in the Willows. Throughout the 1930s, Shepard maintained his work ethic, illustrating fourteen books, dust jackets and frontispieces, and continuing his contributions to Punch. Between 1954-55 Ernest illustrated nine books, traveled, gave lectures, and even wrote two autobiographies: Drawn from Memory (1957) and Drawn from Life (1961).
Ernest continued to draw in his nineties, his last work being the color illustrations for Winnie the Pooh.
(source: https://www.illustrationhistory.org/artists/ernest-howard-shepard)