The success of alien plant species can be attributed to differences in functional traits compared to less successful aliens as well as to native species, and thus their adaptation to environmental conditions. Studies have shown that alien (especially invasive) plant species differ from native species in traits such as specific leaf area (SLA), height, seed size or flowering period, where invasive species showed significantly higher values for these traits. Different environmental conditions, though, may promote the success of native or alien species, leading to competitive exclusion due to dissimilarity in traits between the groups. However, native and alien species can also be similar, with environmental conditions selecting for the same set of traits across species. So far, the effect of traits on invasion success has been studied without considering environmental conditions. To understand this interaction we examined the trait–environment relationship within natives, and two groups of alien plant species differing in times of introduction (archaeophytes vs. neophytes). Further, we investigated the difference between non-invasive and invasive neophytes. We analyzed the relationship between functional traits of 1,300 plant species occurring in 1000 randomly selected grid-cells across Germany and across different climatic conditions and land-cover types. Our results show that temperature, precipitation, the proportion of natural habitats, as well as the number of land-cover patches and geological patches affect archaeophytes and neophytes differently, regarding their level of urbanity (in neophytes negative for all non-urban land covers) and self-pollination (mainly positive for archaeophytes). Similar patterns were observed between non-invasive and invasive neophytes, where additionally, SLA, storage organs and the beginning of flowering were strongly related to several environmental factors. Native species did not express any strong relationship between traits and environment, possibly due to a high internal heterogeneity within this group of species. The relationship between trait and environment was more pronounced in neophytes compared to archaeophytes, and most pronounced in invasive plants. The alien species at different stages of the invasion process showed both similarities and differences in terms of the relationship between traits and the environment, showing that the success of introduced species is context-dependent.