Context Global pollinator decline has motivated much research to understand the underlying mechanisms. Among the multiple pressures threatening pollinators, habitat loss has been suggested as a key-contributing factor. While habitat destruction is often associated with immediate negative impacts, pollinators can also exhibit delayed responses over time. Objectives We used a trait-based approach to investigate how past and current land use at both local and landscape levels impact plant and wild bee communities in grasslands through a functional lens. Methods We measured flower and bee morphological traits that mediate plant–bee trophic linkage in 66 grasslands. Using an extensive database of 20 years of land-use records, we tested the legacy effects of the landscape-level conversion of grassland to crop on flower and bee trait diversity. Results Land-use history was a strong driver of flower and bee trait diversity in grasslands. Particularly, bee trait diversity was lower in landscapes where much of the land was converted from grassland to crop long ago. Bee trait diversity was also strongly driven by plant trait diversity computed with flower traits. However, this relationship was not observed in landscapes with a long history of grassland-to-crop conversion. The effects of land-use history on bee communities were as strong as those of current land use, such as grassland or mass-flowering crop cover in the landscape. Conclusions Habitat loss that occurred long ago in agricultural landscapes alters the relationship between plants and bees over time. The retention of permanent grassland sanctuaries within intensive agricultural landscapes can offset bee decline.