Smith illustrated over sixty books, including notable works like Louisa May Alcott's Little Women and An Old-Fashioned Girl, Henry Wadsworth Longfellow's Evangeline, and Robert Louis Stevenson's A Child's Garden of Verses.

[5] Creating illustrations for children's books or of family life was considered an appropriate career for woman artists because it drew upon maternal instincts.

"[10] Illustration partly became viable as a result of improved color printing processes and a resurgence of book design in England.

Smith's responsibilities included finishing rough sketches, designing borders, and preparing advertising art for the magazine.

Smith later wrote a speech stating that working with Pyle swept away "all the cobwebs and confusions that so beset the path of the art-student.

[15] While studying at Drexel, Smith met Elizabeth Shippen Green and Violet Oakley, both of whom had similar talents and mutual interests.

[5] Alice Carter wrote about the women in The Red Rose Girls: An Uncommon Story of Art and Love for an exhibition of their work at the Norman Rockwell Museum.

Museum Director Laurie Norton Moffatt said, "These women were considered the most influential artists of American domestic life at the turn of the twentieth century.

[5][18] When the artists lost the lease on the Red Rose Inn in 1905,[19] a farmhouse was remodeled by Frank Miles Day for them in West Mount Airy, Philadelphia.

They named their new shared home and workplace "Cogslea", drawn from the initials of their surnames and that of Smith's roommate, Henrietta Cozens.

To help overcome that stereotype, women became "increasingly vocal and confident" in promoting their work as part of the emerging image of the educated, modern and freer "New Woman".

[21] Artists "played crucial roles in representing the New Woman, both by drawing images of the icon and exemplifying this emerging type through their own lives.

Other successful illustrators were Jennie Augusta Brownscombe, Rose O'Neill, Elizabeth Shippen Green, and Violet Oakley.

[34] According to The New York Times in 1910, Smith made about US$12,000 ($392,400 today) per year[35] and, like Norman Rockwell and J. C. Leyendecker, became popular as a "media star".

Biographer Edward D. Nudelman wrote, "The cover illustration for this book, showing two children nestled beneath the wings of Mother Goose, is one of Smith's most pleasing and warm images.

The serenity portrayed in the posture and expression of the children, along with the material concern of Mother Goose, gives evidence of the genius of Smith.

"[42] Smith had a knack for painting children, persuasively using milk, cookies and fairy tales to achieve a relaxed, focused child model.

[40][41] She graced every printed cover of Good Housekeeping from December 1917 through April 1933, creating 184 illustrations of family scenes for the magazine.

Smith worked in mixed media: oil, watercolor, pastels, gouache, charcoal, whatever she felt gave her desired effect.

Such a thing as a paid and trained model is an abomination and a travesty on childhood—a poor little crushed and scared unnatural atom, automatically taking the pose and keeping it in a spiritless, lifeless manner.

[50] Though never a travel enthusiast, Smith finally agreed to tour Europe in 1933 with Isabel Crowder, who was both Henrietta Cozens' niece and also a nurse.

[54] Of the small group of women inducted since then, three were the members of The Red Rose Girls: Jessie Willcox Smith, Elizabeth Shippen Green (1994) and Violet Oakley (1996).

[57] The following collections contain her works: Smith made illustrations for more than 250 periodicals, 200 magazine covers, 60 books, prints, calendars and posters from 1888 to 1932.