Born in
Toko,
Taranaki in 1910, Woollaston attended primary school at Stratford, and then
Stratford Technical High School. In 1931 he studied art at the
Canterbury School of Art in
Christchurch where one of his teachers was
Margaret Stoddart. He became interested in
modernism after moving to
Dunedin to study with R N Field at the art school attached to the
King Edward Technical College. As Woollaston noted in his autobiography
Sage Tea, Field's work ‘conveyed directly, without the intervention of
subject, the excitement of the act of painting'. While at art school, Woollaston met
Rodney Kennedy and the two became lovers and remained life-long friends after Woollaston's marriage in 1936 to Edith Alexander, who had also been an art student in Dunedin. Edith raised their four children. Kennedy went on to become a driving force of avant garde arts in Dunedin and one of the country's leading drama producers. He was an early supporter and collector of Woollaston's work and became the long-term partner of
Charles Brasch, another passionate collector of contemporary New Zealand art. In 1934 Woollaston and his family settled at
Māpua, near
Nelson, but remained part of a close circle of local artists and writers which included
Colin McCahon,
Ursula Bethell,
Charles Brasch and
Ron O'Reilly. Between them they provided ongoing,moral, critical and financial support. In 1936 Woollaston was invited to exhibit with
The Group in Christchurch for the first time, becoming a member in 1940. He went on to participate in 27 exhibitions of The Group and was included in the 1977 retrospective. As a full-time orchard worker Woollaston was exempted from enlistment in World War II and spent most of the forties in the Māpua area. After
the War, in 1950, the family moved to
Greymouth and the landscape of the
West Coast became a major feature of Woollaston's work. He earned his living as a Rawleighs salesman, although the pressure of the job gave him little time for painting. Concerned at Woollaston being side-tracked by his art, the Rawleighs management once cautioned him, that while ‘art might be the cream on your coffee Rawleighs is your bread and butter’. An annual Fellowship awarded by the Federation of New Zealand Art Societies in 1958 enabled him to travel to Australia where he studied old Master paintings at the
National Gallery of Victoria. The Gallery was impressed by Woollaston's work and purchased the painting
Edith with a Lamp along with a number of drawings he had made of works from the Gallery's collection including ''Analytical study of Poussin's 'Crossing of the Red Sea'.'' By the 1960s Woollaston was finally able to paint full-time and earn a living from his work assisted by a second Fellowship grant. In 1962 this second grant allowed a trip to Europe and the United States.
Philip Woollaston, the youngest of Woollaston's four children, kept up the family associations with the area. He was the (Labour) Member of Parliament for
Nelson from 1981 to 1990 and currently manages the Toss Woollaston Trust. Edith Woollaston died in 1987 following a severe stroke, aged 83. After her death, Woollaston became a close friend of Anne Martindell who had been the United States Ambassador to New Zealand from 1979 to 1981. They spent time travelling in the United States together. == Friendship with Colin McCahon ==