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Lagerstroemia indica is an important ornamental tree worldwide. The development of cultivars with colorful leaves and increased ornamental value represents one of the current main research topics. We investigated the anthocyanin profiles in two contrasting cultivars for leaf color phenotypes and explored the underlying molecular basis. Both cultivars display purple-red young leaves (Stage 1), and when the leaves mature (Stage 2), they turn green in HD (Lagerstroemia Dynamite) but remain unchanged in ZD (Lagerstroemia Ebony Embers). Seven different anthocyanins were detected, and globally, the leaves of ZD contained higher levels of anthocyanins than those of HD at the two stages with the most pronounced difference observed at Stage 2. Transcriptome sequencing revealed that in contrast to HD, ZD tends to keep a higher activity level of key genes involved in the flavonoid–anthocyanin biosynthesis pathways throughout the leaf developmental stages in order to maintain the synthesis, accumulation, and modification of anthocyanins. By applying gene co-expression analysis, we detected 19 key MYB regulators were co-expressed with the flavonoid–anthocyanin biosynthetic genes and were found strongly down-regulated in HD. This study lays the foundation for the artificial manipulation of the anthocyanin biosynthesis in order to create new L. indica cultivars with colorful leaves and increased ornamental value. [ABSTRACT FROM AUTHOR]