The phrase identifies outfits inspired by the characters and setting of the film O Brother, Where Art Thou?. These ensembles typically evoke the Depression-era South and the distinctive clothing styles of the escaped convicts and other individuals featured in the movie. Examples include striped prison uniforms, simple work shirts, overalls, and period-appropriate hats.
The appeal of these costumes lies in their recognizability, historical connection, and relative simplicity. They offer an opportunity to embody a specific time period and characters that have gained considerable cultural recognition. The outfits provide a blend of nostalgia and a connection to a celebrated piece of American cinema. The economic hardship and rural setting depicted in the film are often represented in the costume designs.