Trained by Frederick McCubbin at the National Gallery of Victoria Art School, and by painter and printmaker Frank Brangwyn in London, Traill worked in England and France in the period immediately preceding World War I.

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.

[2] Her fellow students were mostly women and included Hilda Rix Nicholas, Norah Gurdon, Ruth Sutherland, Dora Wilson, and Vida Lahey.

[10] Traill's first notable successes were in 1909, when works by the artist were hung at the Paris Salon and London's Royal Academy of Arts,[10] while her first solo show was opened in Melbourne.

When the Australian Painter-Etchers Society in 1932 held its only thematic exhibition, Sydney Harbour Bridge Celebrations, Traill contributed a series of seven prints.

At the time they were created, the artist Arthur Streeton observed: Melbourne should be proud of that fine draughtswoman and etcher Miss Jessie Traill.

[16] Describing the series as "perhaps the finest representations of this genre", National Gallery of Australia curator Roger Butler singled out her Building the Harbour Bridge VI: Nearly complete, June 1931 for comment, with its "towering, skeletal structure framed by foreground cranes".

[19] Reviewing an exhibition of Traill's works, art critic Christopher Allen, writing for The Australian in 2013, considered the images of Sydney Harbour Bridge to be "her greatest achievement".

[21] Butler collected works by Traill throughout his tenure at the National Gallery of Australia, which one reviewer considered was responsible for the "rediscovery of an artist previously almost unknown to the public".

[23] Author and art critic Sasha Grishin reviewed the exhibition for The Canberra Times, concluding that the show "reasserts the supremacy of Jessie Traill as one of the great Australian artists of the 20th century".