Kenneth Whistler Street was born in Woollahra on 28 January 1890. He was educated at Homebush Grammar School, Sydney Grammar School (1903-1908), and at the University of Sydney. He graduated in Arts in 1911, and in Law with second-class honours in 1914, having won the Harris and Wigram Allen Scholarships and the Pitt Cobbett Prize. On the outbreak of the first World War, he secured a commission in the 6th Duke of Comwall's Light Infantry. Sent to France, aggravation of an old football injury caused him to be discharged as unfit for active service, and he returned to Sydney. Between 1915 and 1919 he served with the home forces at the German Concentration Camps in NSW, on the District Headquarters staff in that State, and at Army Headquarters, Melbourne, Victoria.

In 1916 he married Jessie Mary Grey Lillingston, a leading feminist and social activist. The couple had four children, the youngest of whom, Laurence Whistler Street, also became Chief Justice of NSW.

KW Street was admitted to the Bar on 12 March 1915 but did not begin his practice until after the war. He lectured at the Law School of the University of Sydney between 1921 and 1927 on Legal Interpretation, Contracts, Mercantile Law, Torts, and Legal Ethics.

In 1927 the Industrial Commission was reconstituted and he became one of the three original members of the new tribunal, taking his seat on 16 December 1927. Then, in 1931, on the retirement of Sir David Ferguson from the Supreme Court Bench, Street was appointed to fill that vacancy.

On the death of Sir Frederick Jordan, Mr Justice Street was the senior Puisne Judge and Acting Chief Justice. He was elevated to the vacant office on 6 January 1950 and remained as Chief Justice until his seventieth birthday in 1960. In 1952 he became a Knight of St. John of Jerusalem, and in 1956 he was appointed KCMG. The University of Sydney conferred on him the degree of Doctor of Laws ( honoris causa).

From the time of his appointment as Chief justice until his death on 19 February 1972 Sir Kenneth Street was Lieutenant Governor.

During his term of office, he trebled the number of Judges of the Supreme Court in response to the huge increase in litigation which followed World War II. He also improved and expanded the number of courtrooms and support facilities for the Supreme Court. Sir Leslie Herron remarked of him: 'He had a scholarly and erudite knowledge of English literature and a fine command of its language, much of which you will see translated into those illuminating judgments that he gave from his bench.'