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Jennifer Roy has worked in various roles throughout their career. Jennifer started their most recent position as a Sales Floor Team Member at Anatomie Fashion in May 2021. Prior to that, they worked as a Wardrobe Stylist at Pearl by Lela Rose from March 2020 to May 2021. From 2007 to 2021, Jennifer worked at Carlisle and PerSe Collections as a Wardrobe Stylist and later as a Digital Stylist. In 2019, they worked as a Wardrobe Stylist at Worth New York. Jennifer also has experience in sales, having worked as a Manager Catalog Sales at Waterworks from 1997 to 2000, and as a Danbury Store Manager at Jacadi from 1992 to 1996.

Jennifer Roy attended Georgetown University from 1974 to 1978, where they obtained their Bachelor's degree in Russo-European History. Prior to attending Georgetown University, Jennifer Roy completed their high school education at Wilton High School in CT.