Dressy Bessy is an indie rock band from Denver, Colorado, associated with the Elephant Six Collective. Guitarist John Hill also plays with The Apples in Stereo. Lead vocalist/guitarist Tammy Ealom formed the band with drummer Darren Albert and guitarist turned bassist Rob Greene in 1996. The name was taken from a popular Playskool doll of the 1970s. Hill joined around the time they started recording. They released two singles and an EP in 1997-98 and licensed songs to some compilation albums.

Dressy Bessy's first full-length release Pink Hearts, Yellow Moons (1999) was a mixture of beat group drums, infectious songs, and the odd burst of harmonium. Further releases include California EP (2000), Sound Go Round (2002), and 2003's Dressy Bessy, which incorporated a harder guitar sound. 2003 also brought the compilation Little Music: Singles 1997-2002. These albums were initially released on Kindercore Records of Athens, Georgia. Their songs "If You Should Try to Kiss Her" and "Just Like Henry" were featured in the 1999 indie film But I'm A Cheerleader.