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Childish Gambino
The song is linked to a proposed supplemental screenplay that Gambino said would accompany the album's release. Gambino has said in an interview that the title refers to rich people wearing whatever they want.
The song seems to fit a rich-boy theme and is voiced by a character or alter-ego called "The Boy" rather than Gambino himself. In his interview, Gambino described it as the idea that someone rich enough could show up to a black tie affair in sweatpants without anyone objecting.