Shakespeare trained at Dudley Art School and later studied and then taught at Birmingham School of Art. His carefully organised, flatly painted compositions in oils, in which great attention was paid to the outline silhouette of each individual figure, were exhibited at the RA between 1934 and his death in an air raid. He also exhibited at the Paris Salon and the RBSA. In spite of his early demise, his oeuvre has undeniable charm – his essentially suburban, and peculiarly English, compositions are drenched with colour and light and despite sometimes appearing to verge on caricature are usually carried off with great panache.