Wilkinson studied at Portsmouth and Southsea Schools of Art. He began his career as an illustrator in 1898 with the Illustrated London News and went on to design posters for the LNWR, LMS and SR. It was at Wilkinson's suggestion that the LMS commissioned a number of Royal Academy artists to design a successful series of posters in 1924. He worked with the British Admiralty during World War I in designing dazzle camouflage for British ships.