[2] The exact origin of the garment is unknown, although some stories attribute the shirt to the people of the Philippines who introduced the design to Mexico via the Manila-Acapulco galleon trade, from there spreading to Cuba and the rest of the Caribbean.
[2] The Cuban origin story tells of a poor countryside seamstress sewing large patch-pockets onto her husband's shirts for carrying guava (guayabas) from the field.
[4][2] In another version of the story, in 1709 Spanish immigrants from Granada, José Pérez Rodríguez and his wife Encarnación Núñez García arrived in Sancti Spiritus, located along the Yayabo River.
[19] Guayaberas have been worn extensively by a number of Latin American political leaders, including Andrés Manuel López Obrador, Cesar Chavez, Carlos Prío Socarrás, and Fidel Castro.
[17] Michael Manley, populist Jamaican prime minister, specifically advocated for the guayabera as an anti-colonialist mode of dress,[20] and conversely the shirt was later banned in Parliament by the conservative Jamaica Labour Party.
[21] Similarly, Mexican left-wing populist Luis Echeverría advocated for its use in Mexico in part to symbolize rejection of European and American-style business suits.
[8][2] U.S. presidents, including Ronald Reagan, George H. W. Bush, and Barack Obama, have worn the shirts as a sign of solidarity when visiting the Cuban community in Miami[22] and when attending Latin American summits.