During the 1880s he studied art for two years in Paris, where he was influenced by the work of the French Impressionists and James McNeill Whistler. A painting such as Umbrellas in the Rain (1899), painted during his second European trip, reflects his new interest in Post-Impressionist currents, especially in the paintings of Édouard Vuillard and Paul Cézanne and the doctrines of pointillism. Later pictures are composed of floating geometric areas of colour, representing such objects as hats, umbrellas, trees, balloons, and carriage wheels. Many of his works before 1904 were done in watercolour, but after this date he increasingly painted in oils from watercolour sketches. Still mosaic-like in effect, his later works are more abstract in treatment.

Prendergast's works were shown in the controversial Armory Show in New York City (1913), and he exhibited with The Eight (Eight, The).