Kuniyoshi painted Maine Family during one of the summers he spent in Ogunquit, Maine, in the 1920s. An early work, it reflects the simultaneous influences of both the Western modernist idioms and his Japanese artistic heritage. Distortions of scale and perspective resemble a child's depiction of family members in front of their house, complete with front walk, tree, and "pet”—in this case a toy horse. The background buildings, which are represented as simplified rectangles and triangles of color, reflect the artist's exposure to cubist painting in his use of geometric shapes to emphasize the flatness of the picture plane. However, the figures, although curiously angular and possessing Kuniyoshi's characteristic almond-shaped eyes and unnaturally pointed feet, are given bodies that exist as three-dimensional entities in space.
A comparison between the painting and its related drawing suggests that Kuniyoshi added the figure of the girl in the oil as an afterthought. Her startlingly pale face gives her an otherworldly quality that contrasts with the earthiness of the other figures in the scene. Kuniyoshi's inspiration for this approach was quite possibly based on memory portraits in nineteenth-century American folk art. The artist omits a male figure from the “family” group and oddly juxtaposes the formally attired woman with the diaper-clad baby, unusual characteristics of Maine Family. Though the artist disagreed with them, some critics found Kuniyoshi’s whimsical mode of representing New England farm life amusing.
In 1928, twelve years before Duncan Phillips acquired Maine Family, his first work by the artist, he recognized Kuniyoshi as a serious painter who beautifully combined Japanese and American artistic qualities. He admired the oriental quality of the artist's "confident calligraphy, ...stylistic brush writing,...and... arbitrary color chord of ivory and ebony and lacquer red," which appeared throughout Kuniyoshi's oeuvre, as well as the "plasticity" and "vital" evocation of "the inner truth" that Phillips believed he had acquired from Western art. According to Phillips, Kuniyoshi's painting represented a "new idiom of quaint pictorial expression."