Daughter of Mabel Ogilvie and Charles Lillingston, Jessie was born in India and moved with her family to Yulgilbar on the Clarence River, northern NSW, in 1896. She was schooled in England at Wycombe Abbey School, Buckinghamshire, from 1903, returning to Australia in 1906. She graduated in 1910 with a Bachelor of Arts from the University of Sydney, and became a founding member of the Sydney University Women's Sports Association that same year.

From here, a long and active career began with attendance at the International Alliance of Women Conference in Rome in 1911, and Geneva in 1914. Jessie worked for the New York Protection and Probation Association in 1915. She joined the Feminist Club the following year, becoming President in 1928 and resigning in 1929. In 1916 she was Co-founder with Annie Golding of the NSW Social Hygiene Association. That same year she married Kenneth Street. The pair were to have four children: Belinda (1918), Philippa (1919), Roger (1921) and Laurence (1926).

In 1920, Jessie Street became Secretary of the National Council of Women, NSW, and founding member of the Australian League of Nations Union. She was a member of the Women's College Council from 1921-50; member of the Women's League of NSW after its formation in 1926; Foundation Vice-President of the Racial Hygiene Association of NSW in 1926 (renamed the Family Planning Association in 1961); Co-founder of the United Association of Women (UAW) in 1929; and President of the UAW from 1931-42. In 1936, Street was the NSW Vice-President of the Australian Federation of Women Voters. She formed the Council of Action for Equal Pay in 1937, and became President of the Australian Open Door Council the same year. In 1939, Street joined the Australian Labor Party. She was also Australian president of the Society for Cultural Relations with the USSR. The following year she took an equal pay case to the Commonwealth Arbitration Court with Nerida Cohen on behalf of the UAW.

Jessie Street was a member of the NSW Committee of the International Peace Campaign throughout the 1930s-40s. In 1934 she was awarded the Victorian sesquicentennial prize for her song Australia Happy Isle.

Street founded and launched the Australian Women's Digest in 1941. In 1941 she was also Chair of the Russian Medical Aid Comforts Committee, and in 1942, formed the NSW branch of the Council for Women in War Work. She initiated the national conference which led to the Australian Women's Charter in 1943. The following year, as the NSW Chair of the Australian Women's Charter, she led a delegation of 13 women to present the Charter to Parliament.

1943 and 1946 saw two unsuccessful campaigns as Labor candidate for the seat of Wentworth in Sydney, but Street became President of the NSW Peace Council and was the sole woman in the Australian delegation to the founding Conference of the United Nations in San Francisco in 1945. She was the founder of the UN Commission on the Status of Women, 1945, acting as Australian representative from 1945-47, and Vice-President in 1947. Between 1957-67, she campaigned for constitutional change to grant the Aboriginal population the right to vote.

Street travelled extensively between 1945-64, visiting Washington, London, Moscow (as an official guest of the Soviet Union), Paris (for the Women's International Democratic Federation Conference), New Delhi (as guest delegate to the All India Women's Conference, 1945), and New York (for the Status of Women Commission, January-February 1947 and January 1948). Street was invited to Britain to help organise the World Peace Conference in 1950. She travelled throughout Europe on World Peace business in 1951, attending the Women's Congress in Copenhagen in 1953. She travelled to Geneva to observe the United Nations; to Vienna for the World Peace Council; to China on the invitation of the China Peace Committee; to Madras in 1955 for the All India Congress for Peace and Asian Solidarity; to Helsinki for the World Assembly for Peace; and to New York to attend the UN General Assembly. She chaired a seminar on the Status of Women in London in 1956. Between 1958-59, Street attended peace conferences in Stockholm and New Delhi. She was involved with the UN Status of Women Commission in New York; the International Assembly of Women in Copenhagen; and the 6th World Conference against A & H bombs in Japan, 1960-61.

Jessie Street's autobiography, Truth or Repose, was published in 1966. In 1989 the Jessie Street National Women's Library was established in her honour in Sydney, New South Wales.