"Autumn," Marianne von Werefkin, c. 1907.
No, this isn't from the Madeline books by Ludwig Bemelmans, although it's certainly reminiscent. This is a few decades before that.
Russian-born von Werefkin (1860-1938) was a noted Expressionist painter who moved around a bit. She was from a noble Russian family, moved to Munich to immerse herself in the artistic and Expressionist scene (living on a pension from the Tsarist government), and fled to Switzerland at the outbreak of WWI, and experienced hardships after the October Revolution ended her pension and made her a stateless person. She passed away in the city of Ascona, where she is still a popular figure.
Here we have a scene of schoolgirls walking across a park as the sun sets. While cute on the surface, the paired-off students are all separate, and nobody seems to be talking or even looking at the other. Werefkin had a knack for depicting modern alienation, and despite her elite Tsarist background, would depict the common working man with dignity.
From the Museo Comunale d'Arte Moderna, Ascona, Italy.