Oliver Cheshire (born 3 June 1988) is an English male fashion model.
Cheshire was born in London on 3 June 1988. He was scouted by Select Model Management at 15 years of age while studying drama. Soon after Cheshire became an overnight success as the new face for Calvin Klein. Cheshire gave up drama studies for model career. In 2008 he did Jack Wills advertising campaign in Rajasthan, India. Cheshire has also been modeling for Dolce & Gabbana, Missoni, Abercrombie & Fitch, Hollister, Vivienne Westwood, Gap and Marks and Spencer.