The first 'Miss Jamaica' beauty competition took place in 1929, sponsored by the national newspaper the Daily Gleaner, and was closely aligned with planter-merchant interests. The 'Miss Jamaica' beauty contest developed in the 1930s, a decade that witnessed a surge in anticolonial activity: popular uprisings, feminist development, the formation of political parties, and an artistic and literary cultural awakening. However, the 'Miss Jamaica' beauty competition did emerge in resistance to the cultural revolution. An analysis of Herbert G. de Lisser's dedicated construction of idealised white femininity and Marson's and her contemporary Amy Bailey's feminist-nationalist critique of Jamaican national identity was made. Through this analysis, this chapter establishes the context for the origins of a Caribbean beauty competition before the Second World War. Finally, it considers the new beauty competitions which emerged immediately after the war and only for a short time: 'Miss British Caribbean', and 'Miss Kingston'.