Trait-based approaches can provide a generalizable mechanistic understanding of complex post-disturbance succession dynamics of plant communities. Much of our knowledge regarding successional trajectories of functional trait composition come from observations of natural disturbances that leave physical and biological legacy on site for self regeneration. We lack, however, understanding of the long-term recovery in severely degraded lands following reclamation through active revegetation. To address this gap, we examined changes in trait composition of forest understory plant communities in reclaimed oil and gas wellsites using chronosequence data (7–48 years since reclamation) to assess recovery towards that of post-harvest and natural post-fire reference forest sites. We used multiple traits associated with resource acquisition (e.g., fast growth) and performance ability metrics (e.g., shade-tolerance) with putative environmental factors to evaluate the trait-environment relationships underlying plant community recovery in reclaimed sites. We found an overall directional change in functional composition with time since reclamation towards that observed in reference sites, but even older reclaimed sites remained significantly different from reference sites. This could be related to differential trajectory patterns among traits where some trait values progressed towards those of reference (long-distance dispersal by wind decreased with time since reclamation) whereas some fast-resource acquisition traits and exotic species showed no change and remained dominant in older reclaimed sites. The strong link between traits and environment suggests a significant influence of time and subsequent developing site conditions (e.g., canopy cover) as well as enduring legacies of wellsite operation/reclamation (e.g., high soil bulk density and exotic species) on functional composition. Knowledge of functional composition trajectories in severely degraded ecosystems, such as wellsites, could improve our understanding of recovery processes and inform more effective reclamation practices by identifying putative underlying environmental factors and specific ecological attributes that may delay successful recovery.