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Simon began working as a model in his early teens and was eventually discovered, aged 16 by the owner of Boss Models. The catalyst for Simon's success  was when she was shot by Steven Meisel for the cover of Italian Vogue on his 18th birthday.

Due to his height and  hair Simon had always stood out in the modelling industry though he has spoken out about the downsides of his remarkable looks:  “At school I got harassed so badly for being too tall, too thin, too pale – too everything that has gotten me where I am now, which is quite ironic.”

Ever since the Italian Vogue shoot Simon's career has gone from strength to strength, being shot by some of the most prestigious fashion photographers in the world, including Bruce Weber, Mario Testino, Peter Lindbergh and Patrick Demarchelier. Alongside being coveted by the top names in fashion photography. Simon is currently signed to CM Models and Co-signed to Ryan Modeling Agency.