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Holly Letitia Cunningham has a diverse work experience in the fashion industry. Holly Letitia started in 2018 as a Studio Assistant at Teatum Jones, where they gained experience in various aspects of design and production. In 2019, they worked as a Graduate Designer/Exhibitor at the Graduate Fashion Foundation. Holly Letitia then joined Ipsos MORI as a Market Researcher in 2020 and later took on a role as a Fashion Show Assistant at AADNEVIK. In 2019, Holly joined Kiltane Retail as a Keyholder, where they focused on promoting luxury textiles and interacting with global customers. Holly Letitia most recently worked at the Scottish Fashion Association as a Fashion Designer. Holly also has experience as a Digital Designer (Freelance) at DRESSX, showcasing their skills in digital design.

Holly Letitia Cunningham's education history begins in 2014 when they attended Tramway Visual Arts Studio, where they pursued an Advanced Art & Design Portfolio in the field of Fine/Studio Arts. Holly Letitia then went on to The University of Edinburgh from 2015 to 2019, earning a Bachelor of Arts degree with a major in Fashion/Apparel Design. In 2021, Holly enrolled at The Glasgow School of Art and pursued a Master of Design degree in Fashion/Apparel Design, which they completed in 2022. During the same year, they also studied at The Digital Fashion Group, specializing in the fundamentals of Digital Fashion Design. Additionally, Holly participated in the Digital Fashion 101 program at the Parsons School of Design - The New School in 2021 through The Digital Fashion Group: Academy.