While at S.I.T. Fashion Design Studio, Benjamin studied womenswear design, focusing on the creative and technical aspects of creating apparel. After being awarded the Grand Marnier Evening Wear Award in his final year, he went on to launch his first collection under the spotlight of national media and the Australian fashion industry. This recognition led to various collaborations with textile artists, namely Indigenous Australian artist Robyn Caughlin, resulting in a runway presentation at Australian Fashion Week (2003) and a profile in Australian Vogue. Benjamin then moved to London, working for notable brands, including Marchesa (couture), WINTLE (luxury menswear), and Roberto Torretta (womenswear) in Madrid. After 10 years in London, Benjamin relocated to New York, where he was the first Australian designer to be a contestant on Project Runway (season 11), returning to compete in Project Runway All Stars (season 4) the next year. Still based in New York, Benjamin continues to design evening wear for private clients and explore the role of educator. He was the Education Director for the fashion school within the world-famous Mood Fabrics from 2015-2020. For the past six years, Benjamin has also been Head Instructor and Mentor for the Brooklyn Fashion Academy, a program run by Brooklyn Public Library. In 2021, Benjamin became the Studio Technologist for the M.F.A. Fashion Design program at the Fashion Institute of Technology, NYC. He has also taught fashion design for Putney Pre-College programs in Vermont and Barcelona. In 2024, Benjamin began research for his Ph.D. with the University of Technology Sydney (by distance), focusing on sustainability in fashion.