"Not Pretty Enough" is a song by Australian country singer-songwriter Kasey Chambers, produced by her brother Nash Chambers for her second studio album, Barricades & Brickwalls (2001). It was released as the album's third single on 14 January 2002 in Australia as a CD single. It became a number-one hit in Australia the same year, and it also found success in New Zealand, where it reached number four. In the United States, it was serviced to adult album alternative radio in late January 2002.