Understory vegetation is one of the most important links for improving forest biodiversity, and its restoration is conducive to sustainable forest development, energy flow, and nutrient cycling. However, little is known about the developmental dynamics and main driving factors of the long-time series coverage, biomass, diversity, and species composition of plantation understory vegetation. In a case study of three typical plantations, with a natural secondary forest as reference in the Loess Plateau of China, we collected understory vegetation from a Robinia pseudoacacia Linn. deciduous broad-leaved plantation, Pinus tabulaeformis Carr. evergreen coniferous plantation, and mixed plantation with an age span of 10 to 50 years. (1) The understory plantation coverage and biomass results of stands with different ages showed the R. pseudoacacia plantation to be significantly higher than the P. tabulaeformis plantation, and the species diversity of the P. tabulaeformis plantation changed the most with the stand age. However, the growth resource imbalance, and drastic changes in the stands’ environment caused by excessive intraspecific competition in the early stage of the P. tabulaeformis plantation vegetation restoration, are the main reasons that make the species diversity of undergrowth vegetation of P. tabulaeformis plantation lower than that of other stand types. (2) The understory species composition of the plantations revealed their degree of community stability. Compared to the R. pseudoacacia plantation and P. tabulaeformis plantation, the mixed plantation had higher stability, and its species composition closely resembled a natural secondary forest. The community stability of the P. tabulaeformis plantation was the lowest because it had the lowest coverage, biomass, and species diversity of understory vegetation. However, the understory species composition of the three plantation types converged, which was due to atypical species contribution. (3) The dynamic changes of canopy and soil nutrients were the main driving factors affecting the R. pseudoacacia plantation understory vegetation species composition. Stand density and elevation limited the understory vegetation communities of P. tabulaeformis plantation restoration. Soil bulk density is the key factor affecting understory vegetation in mixed plantations, and this effect weakens with the stand age. In future studies, the focus should be on the converged action and further development trend of atypical species, choosing an appropriate recovery strategy (active or passive), and providing more possibilities for the intensive management of vegetation under different plantations.