Culture has played a pivotal role in fashion from time immemorial. The objective of this research is to explore the power of cultural affiliation in fashion. The selected study setting is the Kandyan Kingdom of Sri Lanka. The Kandyan Kingdom of Sri Lanka lasted almost 3 1/2 centuries from 1474-1815. The whole period faced different foreign cultural forces. As a result of such diverse cultural influences the Kandyan dress showed a hybrid formation of Western and South Indian and Sinhalese traditional sartorial features. Sewing techniques and unsewn dress arrangement methods were mixed together. The dress became an amazing blend of Eastern and Western dress items. They combined different aspects of foreign dress together to yield a unique result. The analysis comprises observational study of actual descriptions made by observer- participants, historical records, murals of the period review of ancient literature and research papers relevant to the subject. Reliability of the data was ensured. The pictorial data were cross checked from different literary sources. Many original sources were used. Results: Culture and fashion have strong interconnection. When features of culture change, trends of fashion are gradually correspondingly changed.