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Stick and leaf insects (Insecta: Phasmatodea) are a mesodiverse order of insects distributed across the world. These masters of masquerade crypsis are riddled with analogous morphological characters and lack a robust taxonomic framework. It seems that convergent evolution and the re-evolution of complex traits like wings and ocelli is perhaps the rule rather than the exception in stick insects. To investigate the re-acquisition of traits in this unique study system, a robust phylogenetic framework is essential. Our analyses combine traditional Sanger data with a transcriptomic backbone to provide the most corroborated phylogenetic analyses to date. To accomplish this, we employ a taxon sampling strategy which nearly doubles the number of exemplars in previous studies covering nearly a third of species diversity in Phasmatodea. Ultimately, we found that stick and leaf insects contain rampant taxonomic incongruence and provide a framework for future studies on all aspects of their evolution.