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Abstract PremiseAdaptive radiation in ecologically and morphologically diverse plant lineages presents an opportunity to investigate the rapid evolution of novel floral traits. While some types of floral traits, such as flower color, are well characterized, other types of complex morphologies remain understudied. One example is occluded personate flowers, dorsoventrally compressed flowers with obstructed floral passageways, which have evolved in multiple genera, but have only been characterized from snapdragon. MethodsOur study examined the morphological basis and evolutionary history of personate flowers in a clade ofPenstemonspecies that includes three personate‐flowered species. We characterized floral morphology and inferred phylogenetic relationships for 13 species in this group to examine the evolutionary history of personate flowers. We used phylogenomic tests for introgression to examine whether personate‐flowered lineages have a history of introgression. ResultsUnlike the personate flowers of snapdragon, personate flowers inPenstemonare produced by deep pleats in the ventral petal tissue that curve the ventral petal surface upward, obstructing the floral tube opening. Our phylogenetic tree suggests that personate flowers evolved in two separate lineages. Phylogenomic analyses indicate incomplete lineage sorting and introgression between certain taxa have contributed to phylogenomic discordance; however, we found little evidence of recent introgression between the two personate‐flowered lineages. ConclusionsPersonate flowers inPenstemonhave a different morphological basis than those in snapdragon. Personate flowers have evolved multiple times inPenstemonon a rapid evolutionary timescale. The source of genetic variation for repeated shifts may be de novo mutations or pre‐existing variants.