1950s: The Golden Age of Hawaiian Shirts Entering the 1950s, Hawaiian shirts reach their zenith. Designs become bolder, akin to wearable canvases portraying extravagant tropical elements like oversized flowers, palm trees, and beaches. The complexity of patterns and a rich palette of colors make these shirts fashion focal points, captivating the younger generation, especially those immersed in the realms of rock and pop culture.