Preston began illustrating in 1900 and the following year her works were published in ''
Harper's Bazaar''. She was considered one of the top woman illustrators between 1900 and 1939. Others were
Elizabeth Shippen Green,
Jessie Willcox Smith, and
Violet Oakley. Preston became the first, and for years the only, woman to be an associate member and exhibitor at the
Society of Illustrators. Preston also showed her work with the artists of the informal
Ashcan School. Preston was one of the postcard artists for the movement. From 1902 to 1915, it was a pastime of many Americans to collect postcards. She was a judge to select artwork for 300 billboard across the state of New York.
John French Sloan and
F. Luis Mora were the other judges. Preston was a co-illustrator with her husband, James Moore Preston, on the "Our Horse" story printed in a 1910 edition of ''Everybody's Magazine''. The landmark
Armory Show of 1913 included one of Preston's oil paintings,
Girl with print. She won an award at the
Panama–Pacific Exposition in 1915. Preston played herself in the movie
Our Mutual Girl which was shown in theaters in 1915. In 1920, Preston illustrated two
F. Scott Fitzgerald stories for
The Saturday Evening Post:
Bernice Bobs Her Hair and
Myra Meets His Family. She also illustrated stories published in the
Post by
Mary Roberts Rinehart. Her drawings illustrated articles by
Ring Lardner and
P. G. Wodehouse. ==Later years==