A contemporary interpretation of Dollo's Law is that the evolution of specialized structures is irreversible. Among land plants, reproductive specialization shows a trend toward increasing complexity without reversion, raising questions about evolutionary steps and irreversibility of reproductive complexity. Ferns, exhibit varied reproductive strategies, some are dimorphic (producing separate leaves for photosynthesis and reproduction), while others are monomorphic (where one leaf is used for both photosynthesis and spore dispersal). This diversity provides an opportunity to examine the applicability of Dollo's Law in the evolution of reproductive leaf specialization across plants. We analyzed 118 species in Blechnaceae and Onocleaceae using quantitative morphometrics and phylogenetic comparative methods to test the pillars of Dollo's Law of irreversibility. The evolution of dimorphism in Blechnaceae is neither stepwise nor irreversible, with direct transitions from monomorphism to dimorphism, including several reversions. In contrast, Onocleaceae exhibit irreversibility to monomorphism upon further specialization of fertile leaves for spore dispersal, suggesting that additional specialization, not dimorphism alone, may facilitate irreversibility. These results provide insight into the canalization of fertile-sterile leaf dimorphism in seed plants, where traits like heterospory and ovules lead to further specialization and potential irreversibility. These findings suggest that as new specialized traits evolve alongside pre-existing ones, reversion may become increasingly unlikely.