The West India Regiments (WIR) were infantry units of the British Army recruited from and normally stationed in the British colonies of the Caribbean between 1795 and 1927. In 1888 the two West India Regiments then in existence were reduced to a single unit of two battalions. This regiment differed from similar forces raised in other parts of the British Empire in that it formed an integral part of the regular British Army. In 1958 a new regiment was created following the creation of the Federation of the West Indies with the establishment of three battalions, however, the regiment's existence was short-lived and it was disbanded in 1962 when its personnel were used to establish other units in Jamaica and Trinidad and Tobago. Throughout their history, the regiments were involved in a number of campaigns in the West Indies and Africa, and also took part in the First World War, where they served in the Middle East and East Africa.

The West Indies Federation, also known as the West Indies, the Federation of the West Indies or the West Indian Federation, was a short-lived political union that existed from 3 January 1958 to 31 May 1962. Various islands in the Caribbean that were part of the British Empire, including Trinidad and Tobago, Barbados, Jamaica, and those on the Leeward and Windward Islands, came together to form the Federation, with its capital in Port of Spain, Trinidad and Tobago. The expressed intention of the Federation was to create a political unit that would become independent from Britain as a single state — possibly similar to Canada, the Federation of Australia, or the Federation of Rhodesia and Nyasaland. Before that could happen, the Federation collapsed due to internal political conflicts over how it would be governed or function viably. The formation of a West Indian Federation was encouraged by the United Kingdom, but also requested by West Indian nationalists.