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Sydney R. has a wealth of work experience, beginning with a Sales Associate role at The Beverly Hills Bikini Shop in 2005. Sydney then moved on to American Apparel in 2009, where they were promoted from Team Member to Assistant Manager within 10 months. In 2011, Sydney R. held an Intern role at Berri Goldfarb Public Relations, and in 2012, they worked as a Visual Merchandiser for Paul & Joe, as well as a Wholesale Sales Assistant for Vivienne Westwood. Sydney R. then held a Women's Buyer role at Ron Herman from 2013 to 2015, and a Brand Manager role at The Piece Collective from 2015 to 2017. Sydney currently works as an Account Executive for Jennifer Meyer, Inc.

Sydney R. began their education in 2005, when they graduated from Beverly Hills High School with a High School Diploma. Sydney then attended FIDM from 2010 to 2012, earning an Associate of Arts Degree in Visual Communications. Lastly, they returned to FIDM from 2012 to 2014, where they received a Bachelor of Science (B.S.) in Business, Management, Marketing, and Related Support Services.