He wrote books on drawing techniques, but is best known for his illustrations of Ernest Hemingway's 1952 novel The Old Man and the Sea and the works of Jim Corbett.
[1]: 15 He studied art at Bolt Court under S.G. Boxsius and from October 1940 to January 1946 served as a Leading Aircraftsman in the RAF.
In the 1940s Sheppard wrote and illustrated a number of books for The Studio magazine, explaining techniques on how to draw birds and zoo animals.
This was followed by a successful career as a story illustrator for Lilliput, as well as for leading authors of the day such as Enid Blyton and Jim Corbett.
[1]: 116 He is best known for his original illustrations of The Old Man and the Sea by Ernest Hemingway that he was commissioned to produce at the same time as Charles Tunnicliffe.