After college Simon started designing and making shirts. This brought him to the attention of a local company called the Derby Shirt Company. (A factory formerly known as R. Newbold which used to manufacture shirts for the forces, Police, Army and Ambulance and was later bought by Sir Paul Smith, who turned the name into a designer casual brand still sold today.) The owner of the Derby Shirt Company at the time asked Simon if he would work for the factory part-time and the rest of the week he would be free to concentrate on his own shirts having free access to all the facilities at the factory. Whilst working at the factory Simon was privileged to work on shirt samples for Paul Smith, Ozwald Boateng, Nigel Cabourn, Red or Dead, Comme des Garcon and in particular pattern cut for the Ozwald Boateng shirt collection (notably the collection worn by staff at the “Premier Vision” fabric fair, Paris.) Later Simon took complete control of all shirt production for all of the designers named above.