Fashion gives distinctive meanings. These meanings however subject to constant change because of the context in which any message is transmitted influences its interpretation. There are three kinds of contexts which can be considered in relation to generating meanings in fashion the appearance context, the social context, cultural and historical context in which people lived and interacted. The Kotte era of Sri Lanka from the 15th Century to the 17th Century was a turning point in fashion history where the western fashion (Portuguese) directly influenced. It brought many social and cultural changes due to the changing of the state religion into Christianity. The newly introduced Christian social context led to many changes in royal dresses in the succeeding eras in history because the royalty formed a novel piece of dress fashion by mixed and matched with traditional Sinhala dress features with western dress fashion items. (Hybrid formation) The new fashion brought many new meanings to the Sri Lankan fashion arena. The objective of the research is to find out in what ways the 'context' affect the meanings of fashion. A qualitative method has been adopted for this research. Data were gathered from temple murals, cloth paintings, wood and stone carvings, sculptures and special ivory carvings at Munich Treasury in Germany. Literary data gathered from manuscripts, chronicles, books, original records of foreign travelers, published research and inscriptions. Validity was much concerned. The study reveals that the meaning of dress heavily rely on social contexts in order for a meaning to be comprehended.