Wootton was born in Hampshire, England. He attended art school at the age of fourteen, winning a travel scholarship and a gold medal from the Eastbourne School of Art. In the 1930s, Wootton was commissioned to produce art and book illustrations. At the onset of World War II he volunteered for the Royal Air Force but instead was invited by the commander-in-chief of the Allied Air Forces to accept a special duty commission as official war artist to the Royal Air Force as well as the Royal Canadian Air Force.
It is for this work advancing the field of aviation art, that Wootton is recognized as probably the finest aviation artist of all time. His work is exhibited in private and public collections worldwide, including the Imperial War Museum in London and the National Air and Space Museum in Washington.