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Jessie Stockbridge has enjoyed a multi-faceted career which began in 2004 when she attended the renowned Paul Mitchell The School in Rhode Island, graduating as a licensed cosmetologist. In 2005 she attended the prestigious Ultimate University in Austin Texas and was certified as a Fashion/Runway Makeup Artist.

In 2006 Jessie was recognized by American Salon Magazine for her flawless work with hair extensions. Color correction and natural-looking updo's that reflect the tastes of today's brides are two of Jessie's specialties.

In addition to hair styling she is a freelance makeup artist with a unique flair for colors and is skilled in contouring and corrective makeup. She worked with the Dennis Quaid – Lights, Camera, Fashion Fundraiser in Austin Texas, and was the makeup artist for the Roca Wear clothing catalog in 2007.

In June 2010 Jessie was the key Hair Stylist for episode 1 of the NBC reality show Losing It with Jillian Michaels. Jessie was also chosen to be on the makeup team for The Emerging Trends Fall 2010 Fashion Show during Boston's Fashion week that featured 13 designers and 40 models.