"Unpretty" is a 1999 (see 1999 in music) single recorded by R&B girl group TLC. Produced by Dallas Austin and co-written by Austin and TLC group member Tionne "T-Boz" Watkins, "Unpretty" was the second single released from Fanmail. It became the group's fourth and final U.S. smash hit on the Billboard Hot 100 and their second Billboard smash in a row, following "No Scrubs". It was also nominated for song of the year at 1999 Grammy Awards.

"Unpretty" originated from a poem of the same name written by Watkins, which dealt with a woman's struggle with her self-image. The poem also addressed the comparisons many females make between themselves and the sometimes unrealistic concepts of beauty, as it is commonly portrayed in the media. Upon reading the poem, TLC producer Dallas Austin helped Watkins adapt the poem into a song, which TLC recorded as an empowering song for their mostly female fan base to overcome feelings of physical inadequacy. Watkins and Rozonda "Chilli" Thomas sing lead on the song, with backing vocals by Watkins and Debra Killings. A remixed version, sampling Dennis Edwards & Siedah Garrett's "Don't Look Any Further", was produced by Con?one. Some versions of the remix feature a rap by TLC member Lisa "Left-Eye" Lopes. "Unpretty" was later covered by La Musique Populaire for their 2004 boxed set A Century of Song.

Paul Hunter directed the music video for "Unpretty" in August 1999, which tied together vignettes of several different stories relating to the song's lyrics. The main set of vignettes features a young woman (portrayed by Thomas) whose boyfriend convinces her to get breast implants to augment her small bust. However, after she sees another patient in the hospital (cameo by Jade Valerie) getting her implants painfully removed, the woman flees the hospital in fear.

Another prominent set of vignettes features Lopes as an inner-city woman who witnesses a gang fight and a murder. Several of Lopes' scenes are set to her verse from "I'm Good At Being Bad" (another track on FanMail) instead of "Unpretty" (Lopes appears in the "Unpretty" performance shots reciting the song lyrics in sign language).

Other vignettes feature a full-figured teenager worried about fitting the "ideal" image of the petite supermodel and struggling with a bulimia as a result. Near the end of the video, however, she tears down the unrealistic images of models that she has tacked on her wall, a sign that she may be starting to embrace her own natural body shape. One last set of vignettes features Watkins as a high school student who is harassed by two white males because she is black.

The video has become a fan favorite because it is the last video released in the US featuring all three members of TLC before the death of Lisa "Left-Eye" Lopes. The music video for this song cost over $1.6 million making it one of the most expensive music videos ever made.

"Unpretty" spent three weeks at the top of the U.S. pop chart and was TLC's final number-one single. In the UK, it was TLC's final top 30 hit.