Jessie Traill was born in Brighton, Victoria, on 29 July 1881.
Her father was Scotland-born George Hamilton Traill, who had administered a vanilla plantation in the Seychelles, before becoming a bank manager in Victoria; her mother Jessie Neilley was Tasmanian.

Traill was one of four daughters of George and Jessie, all of them educated at a boarding school in Switzerland, where they learned French and German.
The family were deeply religious Anglicans; two of Traill's sisters would later join religious orders, while Margaret would become a carver.

Returning to Australia, Traill in 1900 studied under John Mather at his Austral Art School, before proceeding to the National Gallery of Victoria Art School from 1902 to 1906, where she was taught by a leading member of the Heidelberg School, Frederick McCubbin.
Her fellow students were mostly women and included Hilda Rix Nicholas, Norah Gurdon, Ruth Sutherland, Dora Wilson, and Vida Lahey.
In March 1906, Traill and her sister Minna, together with her father, sailed for England, while her two older sisters, Kathleen and Elsie, remained in Victoria.
George died while they were travelling in 1907, and is buried in Rome.

Traill studied in London under Anglo-Welsh painter and printmaker Frank Brangwyn, as well as taking classes in summer with him, in Belgium and the Netherlands.
She was the most accomplished student from Australia that he taught.
Jessie Traill was born in Brighton, Victoria, on 29 July 1881. Her father was Scotland-born George Hamilton Traill, who had administered a vanilla plantation in the Seychelles, before becoming a bank manager in Victoria; her mother Jessie Neilley was Tasmanian.
Traill was one of four daughters of George and Jessie, all of them educated at a boarding school in Switzerland, where they learned French and German. The family were deeply religious Anglicans; two of Traill's sisters would later join religious orders, while Margaret would become a carver.
Returning to Australia, Traill in 1900 studied under John Mather at his Austral Art School, before proceeding to the National Gallery of Victoria Art School from 1902 to 1906, where she was taught by a leading member of the Heidelberg School, Frederick McCubbin. Her fellow students were mostly women and included Hilda Rix Nicholas, Norah Gurdon, Ruth Sutherland, Dora Wilson, and Vida Lahey. In March 1906, Traill and her sister Minna, together with her father, sailed for England, while her two older sisters, Kathleen and Elsie, remained in Victoria. George died while they were travelling in 1907, and is buried in Rome.
Traill studied in London under Anglo-Welsh painter and printmaker Frank Brangwyn, as well as taking classes in summer with him, in Belgium and the Netherlands. She was the most accomplished student from Australia that he taught.
Jessie Traill