[1][2] Barry received his education in Europe, first in Heidelberg, Germany, and then at St Paul's School, London.
While at Oxford he also excelled in sports, such as cricket, rowing and he captained the university's first rugby team.
[3] After university he worked in London for a steamship company, studying law part-time.
In 1904 he was admitted to the Inner Temple and next year he returned to South Africa and joined the Pretoria Bar.
He took silk in December 1922 and in June 1926 received an acting judge appointment at the Transvaal Provincial Division.