When David Gandy, the blue-eyed boy from Billericay, fronted a Dolce & Gabbana campaign in nothing but a pair of budgie-smugglers, he hit blast off on a career trajectory towards mainstream stardom (thanks, in part, to a contract with Marks & Spencer). Yet despite social media creating an influencer out of every @tomdickandharry, for years Mr Gandy was in a league of his own.
Then came a chisel-jawed fellow from Hitchin, who was scouted at 15, whisked away to New York at 16 and cast by Calvin Klein Jeans alongside a Russian supermodel named Natalia Vodianova. Hailed as “the new Leonardo DiCaprio” by Select Model Management co-founder Tandy Anderson, Oliver Cheshire went on to work with Vivienne Westwood, Missoni and Paul Smith. His engagement to pop star Pixie Lott followed in 2016 (he proposed on the steps of St Paul’s Cathedral).
Touted as the everyman of modelling – in addition to high fashion brands, he’s helped boost sales for Gap and Superdry – Cheshire is known for being one of the most down-to-earth faces in the industry. Following in Gandy’s footsteps (his Select agency stablemate), Cheshire has also become an ambassador for Jaguar Land Rover. Last summer, the soon-to-be-30-year-old added ‘all-action hero’ to his curriculum vitae when, outside the Natural History Museum, he wrestled an out-of-control cab driver to the ground and helped suppress him until the local constabulary arrived. When did Gandy ever do that?
Have you chosen what you’ll be wearing down the aisle?
“I haven’t fully decided yet, but it’s either going to be a beautifully tailored Marks & Spencer suit – in keeping with the British theme – or I’ll go Italian in a Dolce & Gabbana tuxedo. Both brands have been huge supporters of mine and become like friends and family.”
What sort of brands do you most enjoy working with?
“I love working with those that have an energy and excitement about them, always pushing boundaries in menswear.”
How did it feel to become an ambassador for British powerhouses Marks & Spencer and Jaguar Land Rover?
“I’m extremely lucky to work with two of the country’s most famous and amazing brands. I remember from a young age always wanting to own a Jag – now my dream has come true!”
What makes British style special?
“Britain is the home of tailoring and we still have the number one destination for suiting: Savile Row. We’re also not shy about taking risks when it comes to fashion and that’s why many trends and generations of style and fashion were born here; the whole 60s movement. The mods. The rockers. Punk.”
What’s the key to longevity in modelling?
“To be successful you need to get rebooked on jobs with the same clients. You have to have the ability to adapt with the times and changes in the industry, pretty much like any job. It’s very important to be versatile with your look.”
How has the male modelling industry changed over the course of your career so far?
“Many things have changed since I started. For a start, there’s now GPS on your phone, which makes castings a lot easier. It’s all about social media numbers now. Clients always ask the question: ‘how many followers?’ Advertising budgets have shrunk as more is being spent on social media campaigns. This has given models with a larger number of followers more power in their own right.”
You travel a lot for work. How do you stay in shape?
“Travelling and staying in shape are part of the job description, so it’s important to get loads of sleep, besides the cliché of drinking lots of water. And I always take healthy snacks on long-haul flights.”
Would you like to design a collection yourself?
“It’s always been a dream of mine to design my own fashion collection. I’m actually in the process, and it should be ready for summer.”
Quickfire questions…your favourite city?
Photography by Alexander Beer; Styling by Steven Doan.