After graduating from Royal Holloway and Bedford New College, London University, Sanderson worked in advertising in London before enrolling on the shoe making course at Cordwainers College in East London. Sanderson then worked in Italy first for Sergio Rossi, and later Bruno Magli.

Rupert Sanderson produced his first shoe collection in 2001. By way of reinforcing his design principles, in 2006 Sanderson bought a controlling interest in the shoe factory in the outskirts of Bologna, Italy, that he had been working with from his first collection.

Together with Bertrand Mak, Sanderson co-founded R. SANDERSON, the ultra luxury house of his own label distinguished by the signature 24-carat gold leaf heels and accessories.