After graduating, Garran began to study for the Bar examination. He was employed for a year with a firm of Sydney solicitors, and the next year served as associate to Justice William Charles Windeyer of the Supreme Court of New South Wales.[3] Windeyer had a reputation for being a harsh and inflexible judge, particularly in criminal cases, where he was said to have "a rigorous and unrelenting sense of the retribution that he believed criminal justice demanded, [and] a sympathy verging on the emotional for the victims of crime."[4] Garran however offered a different view, saying that "those who knew him well knew that under a brusque exterior he was the kindest of men", and his reputation had to some degree been created by misrepresentation.[5] In 1891, Garran was admitted to the New South Wales Bar, where he commenced practice as a barrister, primarily working in equity.