With his laid-back demeanour and long wavy hair - a result of two failed attempts to imitate 1960s American singer Bob Dylan's Afro hairstyle - Mr John Tan is often mistaken for a student at the Orita Sinclair School of Design, New Media and the Arts.
New students have asked him which class he is in only to learn that the 29-year-old is actually the school principal.
Mr Tan has been running the boutique design school housed in a three-storey conservation shophouse in the Kampong Glam neighbourhood for two years.
He said: "I think there are benefits in being a young principal. It gives the school a cool and unorthodox principal, and I guess the students find it easier to talk to me than if I were 55 years old."
He said: "I think there are benefits in being a young principal. It gives the school a cool and unorthodox principal, and I guess the students find it easier to talk to me than if I were 55 years old."