Oliver Cheshire

Oliver Cheshire

Interview & Portraits Kirk Truman

“I guess you could say it was an overnight success, you know? It opened doors which I never knew I could walk through…”

After becoming a modelling sensation at the tender age of 16, Oliver Cheshire has gone on to enjoy a hugely successful career as the face of any number of major brands. As he gets ready to launch his first clothing line, he looks back with Journal at half a lifetime in menswear modelling. It’s a grey, autumnal morning when we take a walk through the park. Oliver and I are talking about menswear, his youth and the career which has been his life for almost 15 years. Represented by Fitzrovia-based Select Model Management, Oliver Cheshire is a familiar face on London’s menswear scene whose career as a model and designer has spanned almost half of his lifetime.

Tell me about your upbringing.

As a youngster, I wanted to be an actor so I studied drama. I had a fairly normal working class upbringing. I grew up in a council house with my family. I had a passion for clothing from a young age. I always felt the need to customise my clothes; jeans, shirts, trousers – everything! I can remember my parents thinking I was totally mad at the time. Clothes were a big part of my upbringing. They defined me and my identity.

When were you scouted and what were the immediate effects on your way of life?

I was scouted by Select Model Management when I was 16. I suppose I didn’t really think much of it. I was so young, and at the time I was studying. A few polaroids were taken of me by the agency, and then a few weeks later I visited their offices in Fitzrovia. I’d never been out of the country before in my life, and right then I was told I needed to go to New York City! I was booked by Calvin Klein and then became the face of the brand for a year. As you can imagine, my studies took the back seat and the modelling took over. I guess you could say it was an overnight success, you know? It opened doors which I never knew I could walk through. I was just an ordinary guy standing on the shoulders of giants.

Tell me about the journey.

I was still at school, so the reality of what this becoming still hadn’t really struck me. My first campaign with Calvin Klein was in the first couple of pages of GQ at the time. I was starting to realise that this was definitely about to become a full-time venture for me; the doors to the fashion industry were opening to me. In 2008, I then went on to work on a campaign for Jack Wills in Rajasthan, India. Dolce & Gabbana followed, along with Missoni, Abercrombie & Fitch, Hollister, and Vivienne Westwood. A personal British favourite of mine has always been Marks and Spencer. Today I do a few editorials every couple of months. I’ve become much more selective as time has gone by. What I did when I was younger felt like my apprenticeship years. Now feels like real life. I feel totally secure and ready to explore other ventures.

How do you feel social media has changed the way brands think and reach out to consumers today?

The reality of an image and a marketing campaign is romanticised. Life isn’t this way, and its important for consumers to remember this. Instagram has totally changed the way in which brands strategically think. I guess the reality is now that anybody can become a ‘model’ through platforms like Instagram through creating their own content. What it means to be a model has totally changed now, its become much more human. Character, personality and opinion has perhaps never been more valued in my role. My gut tells me that something like Instagram can’t last forever. I suppose in my heart I feel like there will one day be another platform which will take the throne.

What are your future aspirations?

I’ve always been passionate about clothes. Its been an obsession of mine way before I was scouted or thought this could become a career for me. I’ve always pulled my clothes apart, modified them and personalised them to suit me. What can I say, I’m a total perfectionist! I think I’ve always known that I’ve wanted to start my own clothing line, and now its finally become a reality. My passion for menswear and design was the impetus without a doubt. I’ve worked with some incredible creatives over the years and been a part of this industry for sometime now. It is in part a way to give something back and to also fulfil a dream. The brand is based around simplicity with a focus on sustainability. The designs play with colour and wearability, and encourage men to use colour in a masculine way. The price point is affordable and accessible. The name of the line is taken from the first 3 letters of my surname and the revolutionary, Che Guevara. Che’ will launch in early 2019 and at first will only be available online.