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Koenig has stated in multiple interviews that the album contains lyrical themes of opposition consistent with its title, and feels it is important to understand that the word "Contra" is a fundamental concept of conflict, without any implication that one side is right or wrong. The lyrics of Contra are also meant to express a desire to be compassionate even towards people and things you disagree with. He also states the lyrics of Contra deal with reconciling feeling of privilege and guilt, for which he uses the term "first world guilt". Contra is considered by critics to be instrumental in cementing the cultural significance of Vampire Weekend first formed with their debut record, as Contra deepens and commits to a general attitude of rejecting traditional notions that rock musicians are poor, underprivileged rebels. Whereas their first album brought to light the prejudices against affluence and wealth in rock music, Contra, even in its title, openly argues this stigma.

The band made an effort to make their second album a natural expansion on the universe created in their debut album, as a result Contra covers a far greater gamut of musical influences than their debut album, drawing inspiration from genres such as ska on "Holiday", synthpop on "Giving Up the Gun", speed rap on "California English" and even rave music on "Run". The production of the album, directed by Rostam Batmanglij, was also different from their former work in that it did not use chamber echo and natural reverb but instead used digital effects to give the album an eighties aesthetic. Other distinguishing features of Contra are the use of backing vocals as textural elements, the debut of Rostam as a lead guitarist and more layered drumwork in which fundamental Latin beats are blended with drum machines to create a busier rhythm section.

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