Born in Boston Spa, Yorkshire, the artist's early years were spent at school in Hanover and Rome.  He studied at the Royal institute of Fine Arts in Rome (1919-23), where he was awarded the title of Professor of Architectural Design in 1924. After travelling in Italy and Egypt, he returned to England in 1925 and taught for a year at the Courtauld Institute. During the following six years he exhibited drawings and watercolours in London, became an elected member of Society of Graphic Artists and the British Watercolour Society, studied Chinese calligraphy and Oriental art at the Courtauld Institute, and studied for his architectural degree with his godfather, Sir Herbert Baker ARA FRIBA.

In 1936 he travelled in China, the Gobi Desert, Mongolia, and left Shanghai in August 1937 at the start of the Sino/Japanese war.

Moving to Cornwall in 1948, Oliver taught (Truro School of Art), lectured and exhibited his work throughout Cornwall; he lived in Truro. Later he was made a life member of STISA. In 1956 he had a solo show at the Royal Institution of Cornwall, comprising 75 watercolours, 29 oils and 22 etchings. This was considered to be one of the few shows by a living artist ever held by that institution. Many of his works in a variety of mediums were inspired by his travels to China and Europe, as well as Cornwall, and sold at his own gallery and studio in the 1960's and 70's.