Recent evidence from studies of adolescents suggests that the association between cognitive reappraisal, a well-studied emotion regulation strategy, and well-being may be contingent upon the successfulness of reappraisal attempts. To better determine how adolescents can generate more perceived effective reappraisals, the current study sought to evaluate the originality and linguistic elements of specific reappraisals, including their collective and independent associations with rated regulatory efficacy. We had two goals: 1) assess the relative association between originality, linguistic distancing, and tentative language and rated reappraisal efficacy; 2) evaluate the association between these specific reappraisal components and regulatory efficacy above and beyond general emotion regulation knowledge. Participants (n = 711; 50.8% female, 49.2% male; 15–17 years of age, mean 15.82, SD = 0.74) completed a measure of emotion regulation knowledge and a measure of creative cognitive reappraisal. Above and beyond the variance accounted for by emotion regulation knowledge scores, both more original reappraisals and more temporally distanced language were associated with higher levels of perceived effectiveness. The use of social distancing and tentative language were negatively associated with rated reappraisal efficacy. Originality, distancing, and tentativeness were simultaneously significant, suggesting that they account for unique variance in reappraisal effectiveness.