Jewel wrote this song after being in New York for a week and being around some socialites. She explained: "It's about women – and I include myself, certainly – feeling this need to hide behind something because we don't feel good enough exactly how we are. We have to somehow be prettier or smarter or dress better to be lovable. It's really a song about self-acceptance and learning to love yourself and that 'Plain Jane' is beautiful."
A 'Plain Jane' is a girl who has an average or unattractive appearance – 'Jane' being a US slang term for a woman. Another 'Plain Jane' song is the Eddy Raven tune "Plain Jane Country (Come to Town)," which was recorded by Roy Orbison for his 1972 album Roy Orbison Sings.