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Jessica Cipri has a diverse work experience spanning multiple industries. Jessica began their career as a Seamstress/Sales Associate at Rugby Ralph Lauren in 2008 and also worked as a Sales Associate/Stylist at Martin + Osa during the same year. In 2009, Jessica served as a Fashion Design Intern at Charley 5.0. Jessica then transitioned to the role of International Model Schedule Coordinator at Women's Management in 2010, before joining J.Crew as a Personal Shopper in the same year. At J.Crew, they also held positions as a Merchandise Coordinator and a Senior Creative Operations Associate. Currently, Jessica is employed at Timex Group, where they have worked as a Creative Project Manager, Senior Manager Creative Services, and is now the Director of Creative Operations.

Jessica Cipri completed their Bachelor of Arts degree in Fashion Design and Production from Lasell University from 2006 to 2010. Prior to that, they attended Brookfield High School. Jessica also studied at the Paris American Academy, although the specific years and degree are unknown.