To promote a resilient user-product relationship for sustainable fashion, design methods for emotional durability are required. Digitally transformable fashion design can be seen as a practical approach that enables dynamic, sensory, experiential, and emotional interaction. Literature shows that features of transformable fashion and textiles, such as versatility, perceived quality, biomorphic forms, and aesthetics, can induce emotional durability in users. However, mainstream works are conducted from function-oriented and technology-led perspectives, neglecting the significance of fashion design as a creative and affective role. To fill the gap, we present exhaustive accounts of two autobiographical design projects as case studies: Pneum-Muscle, a body-worn pneumatic wearable, and E-coral, an artistic interactive textile installation. We utilised the first-person soma design method to facilitate the iterative design and unfold the emotional connection between the user and the materials. We contribute technology-embedded fashion design strategies to inspire novice fashion designers, which involve dynamic draping, ambiguous cutting, and sewing technique-based pneumatic systems. Design guidelines generated can shed new light on the artistic use of technologies, somatic design, and the emotionally durable design approach.