Strategically targeting diversity within Brassica oleracea L. could expand existing market classes and products for changing food systems. Consumer acceptance and sensory perceptions of leafy Brassica cultivars have received minimal attention in developing strategic breeding approaches, and few sensory or consumer resources exist to inform the development of new cultivars. We deployed a series of consumer methods to generate a multi-faceted resource for breeding leafy Brassica vegetables with improved quality and potential to innovate produce markets. Qualitative Multivariate Analysis (QMA) identified underlying consumer values associated with kale consumption and highlighted consumer adherence to iconic kale and collard market classes. Quantitative approaches, including a trained descriptive panel and large consumer acceptance study, enabled the identification of 21 sensory attributes (primarily within the texture category) that varied among commercial cultivars and breeding materials. External preference mapping and agglomerative hierarchical clustering (AHC) identified four consumer clusters grouped closely with curly and Tuscan kale genotypes. In-situ sensory testing of collard genotypes in Upstate New York and Western Kenya underscored key considerations in conducting cross-cultural sensory studies. Flash Profiling (FP) with untrained consumer panels elucidated descriptive attributes in the consumer lexicon, while the number of attributes generated by regional panels did not closely correlate with familiarity or ability to differentiate products. Regional collard preferences were identified by a significant (p < 0.05) country-by-cultivar interaction for consumer acceptance. Eight morphologically distinct B. oleracea inbred lines were used as parents to develop a half-diallel mating design, which was subject to genotyping-by-sequencing (GBS), preliminary nutritional analyses, and an online consumer acceptance survey. After accounting for a strong correlation between liking and familiarity, a small heritable (h2 = 0.37) genetic component of consumer liking was identified. Genetic characterization of breeding materials confirmed their potential to add diversity to commercial market classes. Partiality to familiar kale and collard genotypes was a common theme throughout these studies. Continued interdisciplinary work is required to understand barriers to mitigate familiarity and introduce successful cultivars. This research serves as an important resource to leafy Brassica breeding and provides several models to integrate consumer research into breeding programs working with diverse or new crop types.