This comprehensive review is on the dominance of digital technology in fashion design, aesthetics, and profound jounce on the values of individuals in contemporary society. A commensurate understanding of the relationship between digital technology, aesthetics and fashion design is essential to examine the developments, transformation, and socio-cultural surprises in the years to come. Hence, the aim of this research is to bequeath insight and impart new knowledge to the literature encapsulating the following complex interplay between digital technology, fashion design and aesthetics impacting the psychological influences and emotional contagion in the society : (i) introduction of the world of wearables (WOW) that crosses boundaries between many disciplines using wearable operating system (WOS), (ii) describes the indispensable pillars of design imagination that express the product's defining points of importance, (iii) demonstrates digital transformation is a mindset than about technology for the fashion design and development process, (iv) reveals aesthetics as 5C (comfort, communication, care, convenience, and context of usability) experience that actualize user bond and loyalty, (v) justifies fusion of digital technology, aesthetics, and fashion design that offers an array of amazing advantages that creates value for the consumer, (vi) characterizes the power of digital technology on fashion industry creating pervasive phenomenon in the contemporary society, (vii) deliberation and critical rumination on the fashion designer-a bridge between the technology and the consumer that prominence the socio-cultural changes globally, (viii) concludes "less is more" is a key guideline for smart fashion wearable (SFW) design and substantiates that designers will not succeed until it is designed from the fashion perspectivenot as technology that can be worn, but as fashion design that contains technology.