Sustainable fashion has arisen to combat the problems of pollution and climate change, which are results of the consumption of fast fashion. Transformable clothing, a niche segment of sustainable fashion, consolidates multiple functions and aesthetics within a single garment of clothing. It offers a potential pathway to reduce overconsumption, yet fast fashion continues to dominate the market despite positive consumer views. This study investigates the barriers and drivers to adopting transformable clothing and why positive attitudes about sustainability do not translate directly into purchasing behavior, examining lifestyle choices for a correlation. The hypotheses of this study are guided by the Theory of Planned Behavior, examining how aesthetics, usability, and perceived ease of use influence purchase intention and willingness to pay. The research follows a mixed-method design, using a structured survey with visual stimuli of contrasting transformable garment prototypes and randomized framings to describe the business behind the garments’ creation. This approach tests whether the prototypes and framings produce different levels of interest and perceived value. Interviews further contextualize decision drivers across lifestyle segments, including travel frequency, nightlife participation, and storage constraints. In hopes of guiding designers and brands on messaging for transformable items, this study will identify high-potential consumer segments through positioning transformability as having functional and sustainable value.