Ashley left Singapore in 1996 to take a pattern cutting course at the London College of Fashion, and was later accepted into Middlesex University afterwards, but left before completing his degree.
He set up his own label "Ashley Isham" in 2000. In 2001, he also opened a boutique called Acquaint, hoping to "promote fashion talent and support other young designers", quoted from his website. He first attracted media attention as the designer of the outfit worn by Zara Phillips at Royal Ascot in 2002, and rose to international fame after showing his Autumn/Winter 2003 collection during the London Fashion Week. Following this, he opened his flagship boutique, Ashley, in 2005.
- Kolesnikov-Jessop, Sonia (2005-10-06). "Young Singapore designers set sights on international runways". International Herald Tribune. Retrieved 2008-01-28.
- Davies, Caroline (2002-06-21). "Ladies' Day for Zara is matter of convenience". The Daily Telegraph. Retrieved 2008-01-28.
- Sherwood, James (2003-03-12). "Are shows a 'media circus' or a way to showcase talent?: London fashion's dilemma". International Herald Tribune. Archived from the original on 2008-03-23. Retrieved 2008-01-28.
- Cartner-Morley, Jess (2003-09-26). "Left, right, left right, left...". The Guardian. Retrieved 2008-01-28.
- Robson, Julia (2005-02-18). "London: the grande dame of British style undergoes a very subtle facelift". The Daily Telegraph. Retrieved 2008-01-28.