Abstract: Landscape architects are responsible for ensuring the structural stabilization and the high-efficiency of the ecosystem services of plantings in urban rain gardens, and also adapt more attractive rain garden plantings with requiring less inputs for their establishment and maintenance. In this paper, we address the existing problems of the planting design in the current rain garden applications, and introduce the idea of the new naturalistic herbaceous planting for upgrading urban rain gardens. We provide the design of the new naturalistic herbaceous rain garden planting by explaining the plant selection for satisfying the dynamic moisture distribution in rain garden habitat and the "disciplined chaos" strategy for establishing attractive plant community by learning from the nature.