Jean competed in the Miss Texas Teen USA pageant from 2002 to 2004.  She was a semifinalist in both 2003 and 2004 and held the local title Miss Houston Teen USA in 2003.  In these pageants, she competed alongside future Miss Texas USA Lauren Lanning (2006) and Magen Ellis (2007). Jean (as Cassandra Whitehead) won Miss Corpus Christi 2004, a title held by Eva Longoria in 1998. She made the top 10 at Miss Texas USA 2005. Whitehead competed in the Miss California USA 2008 pageant but was disqualified due to her appearance on America's Next Top Model.  The following year she was a judge for the Miss Newport Beach pageant. Whitehead was a 19-year-old student at Texas A&M University–Corpus Christi while participating in America's Next Top Model.