Oliver Cheshire started his career in the fashion industry when he was scouted by Select Model Management in 2003. Referred to as the next Leonardo DiCaprio he secured his debut campaign when he was just 17 years old for American powerhouse Calvin Klein fronting their iconic advertising.
He has gone on to work for some of the biggest names in fashion; Dolce and Gabbana, Versace, Missoni, Vivienne Westwood, Acne and Fillipa-K and with world famous photographers Bruce Weber, Mario Testino, Mert & Marcus and Steven Klein to name a few.
Over the years Oliver has graced the covers of many prestigious publications including L’Officiel Homme, Attitude, The Journal, Men’s Folio, D’Scene, Exalt, 7th Man, Out Magazine, GQ Style with more covers to come. Making his mark on the industry scene he continues to grow from strength to strength making him a permanent fixture on the front row of London, Milan, Paris and New York fashion week.
His savvy smart street style, which is a big hit with young men and women alike, has given him a constant growing and counting.High street giant Marks and Spencer recognised Oliver’s popular and unique broad appeal and have contracted him to front their mens fashion favourite `Autograph` range for the fifth year in a row
Oliver was a guest on the Cannes Red Carpet for luxury jewellery brand Chopard, where he wowed the international media and paparazzi wearing the exclusive designs of Dior and John Varvatos. And, as a favourite of designers Dolce and Gabbana he has hosted their exclusive Alto Sartorio party for D&G and regularly walks their shows. Oliver’s style and in depth knowledge of men’s fashion made him the natural choice to become contributor for “Telegraph Men” in 2013.In 2014 Eva Longoria invited Oliver to present her annual Global Gift Gala in London, alongside American actress Meghan Markle. He continues to supports this event, and Mens Prostrate Charity `One For the Boys` with Samuel L Jackson.
Oliver is now one of Mr Porters “Style Councillors” and recognised supporter of LFWM attending the shows in London, Paris, Milan and NY. Also to note his most recent role as a mentor and judge on the men’s panel at the GQ Grooming Awards and the internationally renowned Jasmin Fragrance Awards, also as a guest speaker at the Glamour Festival discussing men’s grooming in 2016.2017 Oliver was delighted to present the award for Best New Male Design & Packaging at the Fragrance Foundation.
He is regularly heralded in GQ.com’s best-dressed poll in the US and UK, and in Grazia, The Telegraph and Tatler magazine to name a few. GQ USA also featured Oliver on their best dressed list (the only British model to be featured). As an industry favourite he has received awards for `International Model of the Year` from GQ Turkey and two awards from Attitude for “Most Stylish Man” and “Best Groomed Man”.
2020 holds some very exciting projects for Oliver- so watch this space!