Charles Tole was educated at Sacred Heart College and Auckland University College and became a civil servant. He started painting with oil paints on prepared boards around 1940 when he was 37 years old. John Tole had taken some lessons in how to work in oils from the English immigrant landscape painter Walter Wright, who, with brother Frank Wright, operated a painting studio in Victoria Arcade at the bottom of Shortland Street. For 25 years until 1965, Charles Tole’s painting was a hobby, and limited to weekends and holidays with perhaps one or two exhibitions a year. He worked in oil and occasionally tempera, and restricted himself to landscape and still life subjects. After he retired at the age of 62, he started to experiment with collage. A 1968 work entitled “Christmas is no time for cutting corners on sherry” is one memorable result. Charles Tole entered his work into Benson and Hedges competitions and received favourable reviews from knowledgeable critics like Gordon H. Brown who saw the resemblance of his cubist regionalism to the Americans Charles Sheeler and Charles Demuth of the early twentieth century. John Cawte Beaglehole, in opening an exhibition of paintings by Charles and John Tole at the Architectural Centre Gallery in Wellington in 1957, remarked that he thought of the Toles as twins with their hard design and romantic colour.