Hilary Duff accepted the lead role because Charles Perrault's story "Cinderella" was her favorite fairy tale when she was growing up.
Rupert Grint won the role of Austin Ames, but had to drop out due to commitments to Harry Potter e o Prisioneiro de Azkaban (2004). The role of Austin Ames instead went to Chad Michael Murray.
In preparation for her driving test, Hilary Duff drove herself between filming locations during principal photography for this movie.
Many characters have distinct color schemes: Samantha Montgomery and Austin Ames primarily wear blue, Fiona primarily wears pink, Brianna primarily wears green, and Gabriella primarily wears red. Almost all of these tie-in to the color schemes of their corresponding characters in Disney's Cinderella (1950).