Gilder aspired to be an oil painter, and often did the accompanying illustrations for her husband's books of poetry, like
Two Worlds: and Other Poems. Helena de Kay Gilder's best known work was cited as "her figure pictures, 'The Young Mother' and 'The Last Arrow' " by
The Art Amateur. Her impact on the art world spread beyond her own art production. Gilder contributed to the art world by helping to organize the
Arts Student League in 1875, and co-found Her motivation for starting the organization occurred after she showed one painting at
The National Academy of Design's annual show, while she was there as a student. Her painting received a poor location within the show and she felt her paintings location reflected the academy's reluctance to accept new types of art. The goal of the
Society of American Artists was to move in a different direction than the National Academy and other conventional artists groups, while showing that art is valid in many different forms and styles, and can be left up to the artist. Along with Gilder, writers including
Clarence Cook, Charles de Kay, Richard C. Brown, and her husband Richard Watson Gilder criticized the conservative mindset of the
National Academy of Design. == Cultivation of artists and portraiture ==