The image was taken in 1988 when she was just fourteen, by David Ross. This is understood to be the now 38-year-old model's first professional sitting after she was talent spotted at an airport a few months prior, reported Daily Mail online.
The black and white photograph is expected to fetch up to 1,200 pounds when it is auctioned off at Bloomsbury's in Mayfair on November 23.
There are three different photos from Moss's first shoot going up for sale next week.
Photographer Ross, now 47, still remembers meeting the teenage model, who is wearing a Fred Perry sweatshirt in the photos.
"She was a cool character. She seemed like a tough or resilient typical teenager, comfortably fronting me up, perhaps covering up her nerves. I suppose what was refreshing was that she was honest. She wasn't trying to prove anything or act above her station," he said.
"She didn't try to adopt a model attitude of self-absorption and superiority, which at the time was becoming public via media sensation. She was untarnished. A blank canvas, as other writers have put it," Ross added.
Moss was discovered by a talent scout when she was waiting to board a flight back to London from New York in 1988.
Over the last twenty four years, she has been consistently working, fronting some of the world's most iconic campaigns and cementing her reputation as a style icon.
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