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Ashley Leafer has a diverse work experience in the fashion industry. Ashley began their career as a Fashion Specialist at Arden B in 2007. Ashley then interned at Burberry in 2009 and later worked as a Sales Associate at Saks Fifth Avenue in 2011. In the same year, they joined Kenneth Cole Productions as an Assistant Designer at NYC Knitwear. Ashley also took on temporary positions as Men's Shoe Coordinator and Intern at Kenneth Cole Productions. From 2012 onwards, Ashley worked at Kenneth Cole Productions as a Ladies Footwear Designer, responsible for designing footwear for various product lines. Ashley then transitioned into the role of Senior Footwear Designer at Steve Madden in 2017. Throughout their career, they have displayed a strong ability to collaborate with customers and build buyer relationships, while also managing production calendars and ensuring timely delivery of samples.

Ashley Leafer completed their Bachelor's of Science degree in Textile Merchandising and Design, and Art from the University of Rhode Island. Ashley attended this institution from 2006 to 2010. Additionally, Ashley has taken courses in Adobe Illustrator and Photoshop from the Fashion Institute of Technology, though specific dates of attendance were not provided.