Some organs in evolutionary history appear to have emerged without clear precursors and transitional forms, challenging the gradualist assumptions central to Darwinian theory. Strikingly, studies focusing on such evolutionary novelties remain limited to a few well-characterized cases. This review examines two instructive examples in insects that illustrate distinct pathways to fundamental phenotypic innovation. The first concerns the origin of insect wings, undoubtedly one of the most significant and extensively studied morphological novelties in arthropods. Since the early post-Darwinian era, two competing explanatory models have dominated the debate: the paranotal lobe hypothesis and the leg-exite hypothesis. Recent evo-devo research has reshaped this discourse, culminating in the integrative dual origin hypothesis. However, emerging evidence has reignited the controversy, suggesting that wing evolution may be more complex than previously thought. The second example focuses on wing-associated circulatory organs, evolutionary novelties that have received comparatively little attention. These small pumping units drive hemolymph flow through the wing vein network, a mechanism essential for maintaining sensory structures on the wings and preserving cuticular hydration, which is critical for their biomechanical performance. While the ancestral condition is represented by modifications of the dorsal vessel, fully independent wing hearts have evolved multiple times across various insect lineages as novel pulsatile organs. Their emergence appears to be a consequence of spatial constraints imposed by the progressive evolution of the insect flight apparatus. Research in Drosophila revealed that these organs originate from four pericardial precursor cells and represent evolutionary novelties in the strictest sense, as they not only lack homology with any known ancestral structure but also develop as discrete modules under the control of unique gene regulatory networks. Wing hearts thus represent a versatile and experimentally accessible model system for studying the emergence and integration of novel traits — a central, yet still underexplored theme in evolutionary biology.