"Unpretty" is a song by American girl group TLC. It was produced by Dallas Austin. It was co-written by Austin and TLC member Tionne "T-Boz" Watkins. It was for the band's third album, FanMail (1999). The song was based on a poem of the same name written by Watkins. It was about a woman's struggle with her self-image. It talked about the concept of beauty portrayed in the media. Austin helped Watkins to help the song become an empowerment for women who do not think they are beautiful enough.
"Unpretty" was the second single released from FanMail. It became the group's fourth US number one single on the Billboard Hot 100. It spent three weeks at number one. It was considered a success by music critics. It was nominated for Song of the Year and Best Pop Performance by a Duo or Group with Vocal at the 42nd annual Grammy Awards. A remixed version of the song was released.