Cheshire completed the "Certificat pratique de langue française" at the Sorbonne in Paris. She earned her B.A. at the London School of Economics and her Ph.D. at the University of Reading. She has been a lecturer at the University of Bath and University of Reading, a lecturer and then senior lecturer at Birkbeck College London from 1983–91, and professor of English linguistics at the University of Fribourg and the University of Neuchâtel, Switzerland from 1991-96. She is currently a professor of linguistics at Queen Mary, University of London.