Back on land for eighth grade, Leigh began modeling, working consistently for the next few years. As the tedium of modeling set in, Chyler branched out into acting, appearing in local commercials and hosting a syndicated teen news show called "Hall Pass" (1996). She experienced her very first whirlwind television pilot season in 1999 and was cast in a starring role on The WB comedy pilot, "Saving Graces" (1999). While the series didn't make the schedule, Leigh's breakout performance landed her a newly created role on "Safe Harbor".
When not working, Leigh enjoys all kinds of water sports, including sailing, surfing, scuba diving and snorkeling. While working on "Safe Harbor", she divided her time between the set in Jacksonville, Fla., and her home in Miami.