This chapter presents an exploratory study involving a group of athletic shoe enthusiasts and their feelings towards customized footwear. These "sneakerheads" demonstrate their infatuation with sneakers via activities ranging from creating catalogs of custom shoes to buying and selling rare athletic footwear online. The key characteristic these individuals share is that, for them, athletic shoes are a fundamental fashion accessory stepped in symbolism and meaning. A series of in-depth interviews utilizing the Zaltman Metaphor Elicitation Technique (ZMET) provide a better understanding of how issues such as art, self-expression, exclusivity, peer recognition, and counterfeit goods interact with the mass customization of symbolic products by category experts.