Design has recently been recognized as problem solving activity. This research was an effort to unravel comprehension of the complex activity of design and developing an insight of the nature and methodology in which creative thinking skills are put together in the user-centered mannerism of thriving contemporary clothing design for physically challenged. User Centered Design approach requires a great deal of involvement from the users during the whole process of designing. The challenge of design is more pronounced when special problems of the aged, infirm and handicapped arise for solutions. This study comprises of a collaborative workshop to explore and compare dissimilar design practices. The transformed approach to design methodology of prioritizing understandability and usability over aesthetics and technology is found to be more efficient. This new wave in favor of user centered design is now more than only a method rather it is emerging as the new mindset for interpretation of problems of design for twenty first century