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Born in England in 1909 but sent to Canada in his teens, he apprenticed with printers in Toronto in the 1920s and learned the graphic design trade along the way. He struck out on his own in 1930, and built a successful design practice on corporate work and illustration, including several covers for Maclean's. During this period he was active in Toronto's Arts and Letters Club, a 'home away from home' for him throughout his life. He was also a regular part-time instructor at the Ontario College of Art. In World War II he registered as a conscientious objector, and created several well-known war posters, then became a camouflage designer in Halifax, Nova Scotia. In late 1942 he heard that Ottawa was looking for volunteers for its new War Artist program. He applied and was accepted, receiving a commission in the RCAF. He became a Varsity Graduate in April 1948. During the years 1943-6 he produced over one hundred drawings and paintings in watercolours and oils that remain the property of The Crown and reside permanently with the Canadian War Museum.
He returned to his Toronto design practice in late 1945. When Frank Carmichael died suddenly he found himself in charge of OCA's New School of Design. Educational administration was not for him and he resigned in 1946. His celebrity as a returned war artist helped him land high-profile mural commissions with the Sunnybrook Hospital and Ontario Hydro.
In 1954, along with a handful of artists including Frederick Varley, he visited the Soviet Union on the first Canadian cultural exchange of the Cold War, and documented his travels in a Maclean's article. Although he was never a communist and undertook this visit out of curiosity, it is likely that this visit made him ideologically 'suspect' and may have adversely affected his career from this point forward.
As a mature designer, he continued to work steadily during the 1950s, counting as his clients Imperial Oil, the University of Toronto, Ryerson, York University and the Stratford Festival. He was not a prolific fine artist, however, which guaranteed an obscure profile in comparison to other war artists, such as Alex Colville, Lawren Harris or Jack Shadbolt.
Aldwinckle was an out-of-the-box thinker decades before the term became popular. He was a student of comparative religion, an accomplished chef, raconteur, astrologer, composer of music, playwright, writer, and social critic. He enjoyed mentoring young artists, and influenced the careers of the late composer Harry Somers, Academy Award-winning filmmaker Christopher Chapman, muralist York Wilson and designer Theo Dimson.
While his work as a war artist was his most visible contribution, perhaps his most enduring legacy will be his role in the establishment of Killarney Provincial Park, the area where members of the Group of Seven (artists) painted some of their most influential works.