In 1888 Smith graduated from the Academy and the same year her first published illustration entitled Three Little Maidens All in a Row, appeared in the May issue of St. Nicholas Magazine. Her first job was actually with a notions firm called Dreka in Philadelphia and the first art work she sold were place cards with little Japanese figures that she had painted on them. .
Eventually in 1889 Smith found a more secure position as an illustrator with the Ladies" Home Journal in 1889. Initially, her assignments were limited to supportive work for some of the established artists, but soon her skill as an accomplished artist gained appreciation and there was a demand for her work by various national advertisers. Her illustrations appeared in advertisements for a variety of products, such as gloves, root beer, stove and facial soap. She had hope that her illustration work with the major magazine would be a valuable stepping stone to book illustration. Her first book illustrations which were in black and white appeared in a book of poems entitled New and True by Mary Wiley Stauer.
Eager to broaden her experience in the art world Jessie Wilcox Smith entered the Drexel Institute of Arts in 1894.
While studying under Howard Pyle, Smith worked on a series of paintings that were published as illustrations for the book Evangeline by Henry Wadsworth Longfellow. Smith's illustrations for this work were of a delicate nature, possessing a certain graphic quality. The medium was gouche, a method of watercolor painting using opaque colors. Pen and ink was used liberally as a highlight, and the end result yielded a softness which was quite unique and pleasing to the eye. Her illustrations for Evangeline captured a sort of dreamy element which was to be a characteristic quality in her art throughout her career. In the illustration on the front is captioned "Fair in south was the maiden". [Colorplate 90], one can see this imaginative element in the posture and open gaze of a woman standing in a field.