This study aims to merge Picasso’s expressive elements and deconstructive fashion’s formative traits, proposing an upcycle fashion design that fuses artistic and philosophical aspects. The analysis of Picasso’s Cubism identified qualities like liberating revolution, fluidity of vision, geometric reducibility, complex symbolism, and creative imitation. The analysis of Derrida’s deconstructionism revealed expressive traits: uncertainty, intertextuality, différance, and dis-de phenomenon. An upscale fashion design was developed based on six Picasso works featuring women. The design was created using the fashion design software CLO 3D and integrated clothing waste and scrap fabrics as materials.The results are as follows. First, upcycle fashion was viewed from a new perspective based on Picasso and Derrida’s values. This perspective suggested creating better ethical values by upholding environmental protection in novel ways that overcome limitations rather than destroy existing values indiscriminately. Second, upcycle fashion design methodologies were derived from various perspectives utilizing formative features of Picasso’s works and specific expressive features of deconstructed fashion. Third, the direction of mitigating waste and pollution from clothing production and transportation was revealed by making clothes in a virtual space using the CLO 3D program. This study contributed to obtaining various methods for developing upcycle fashion designs using own methods of Picasso and Derrida to diversify the approaches of upcycling, which is relatively stagnant in disassembling.