Oliver Cheshire

Oliver Cheshire is an English model from Hitchin whose career began with Calvin Klein advertising and developed into a long association with Marks & Spencer. His work in menswear also led him into design as the co-founder and creative director of resortwear label Ché.

Scouted at the Clothes Show at 15, Oliver joined Select and began modeling at 16. Recalling his early career in a 2019 conversation with TheIndustry.fashion, he described a first assignment for Tank, followed within weeks by an invitation to audition for Calvin Klein. The resulting campaign gave him an early international booking, though he remembered the years that followed as an apprenticeship, with magazine work helping him develop his interest in clothes.

He also valued the continuity of his relationship with Marks & Spencer in a profession that frequently moved on to new faces. That relationship made him a recurring figure in British menswear advertising. His fall-winter 2013 campaign for Marks & Spencer preceded his role as the face of its relaunched Autograph menswear collection in 2015. Work for Dolce & Gabbana and Versace formed another part of his modeling portfolio.

Oliver co-founded Ché with Toby Watkins in 2018, releasing its first collection in 2019. In an interview with Ounass, he traced his creative education to the designers and stylists he encountered through modeling, describing how those experiences helped him establish his own approach. Resortwear gave that interest a specific direction, beginning with swim shorts and shirts. A 2022 collaboration with Reiss brought his two roles together, with Oliver developing the collection and appearing in its imagery.