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Robert Chafin has over 20 years of experience in the fashion industry. Robert began their career in 1998 at Gucci, where they held the roles of Assistant MRTW Buyer and Assistant Sales/Assistant MRTW Manager. In 2002, they moved to Prada as an Assistant MRTW Buyer. In 2003, they took the role of Merchandising Manager at Gap Inc. and then in 2004, they were the Director Women's Buying - Emporio Armani Division at Giorgio Armani. In 2007, they were a Senior Accessories Buyer at Yves Saint Laurent. From 2011 to 2013, they were the Director of Merchandising at Ermenegildo Zegna and then an Area Manager at Gucci. In 2014, they were the District Manager - Southeast/Midwest at SMCP (Sandro, Maje, Claudie Pierlot) - MAJE and the General Manager - Miami Design District at Giorgio Armani. In 2021, Robert Chafin became the General Manager at John Elliott.

Robert Chafin attended the University of Arkansas from 1995 to 1998, where they earned a Bachelor of Science in Business Administration (BSBA) degree in Economics.