Oliver Cheshire’s Stroke of Success

THE MIDAS TOUCH. As we celebrate the magazine’s 10th anniversary, we meet up once again with British model, gentleman and all-around awesome fellow Oliver Cheshire

Oliver Cheshire

Outfit by Hermès

Life has been good for Oliver Cheshire. Only a month after signing up with his first modeling agency—Select Model Management, which still represents him today—the Londoner was asked to model for Calvin Klein. Since then, he has become the face of fashion campaigns for Abercrombie & Fitch and Vivienne Westwood to Missoni and Dolce & Gabbana. More importantly, quite a few brands started noticing increased sales after he appeared in their respective campaigns.

And now, life seems to continue being good—even great—for Oliver Cheshire. For one, he now sports a new look as he dyed his hair blond shortly before heading out to Jakarta for this photo shoot. He has landed a coveted multi-year contract with Marks & Spencer, which is a huge deal in his home country as the brand has grown into somewhat of a beloved national institution in the U.K. More than that, late last year, Cheshire became engaged to his long-time girlfriend: English singer, songwriter and actor Pixie Lott. In fact, the two have basically become England’s current “it couple,” from appearing together at various high-profile events, walking the runway together at Dolce & Gabbana’s fall/winter 2017 menswear show together and posing together in a number of editorials that have become the talk of the fashion world.

Oliver Cheshire

Pants by Calvin Klein

The chemistry between Cheshire and Lott, as well as the couple’s combined star power, was quite evident as the pair visited Jakarta to attend this year’s DAMAN Party as the guests of honor. So, naturally, we wanted to know even more about the the man behind the model persona and sat down for a chat with Cheshire.
Also, before we delve into the interview proper, just a quick reminder to check out our website and social media accounts for more exclusive content and videos featuring Cheshire and the ever-gorgeous Pixie Lott.

Oliver Cheshire

Outfit and sandals by Louis Vuitton

DA MAN: We last caught up with you for the fall/winter issue of DAMAN Style in 2016. What have you been busy with since then?
Oliver Cheshire: I’ve been working very closely with Marks & Spencer as I’m part of their Autograph range. I’ve also been doing a bit of designing with them. I walked the Dolce & Gabbana show with my fiancée, Pixie. Traveling the world as well, to New York, to Sweden and finally here in Jakarta again.

Oliver Cheshire

Outfit and sandals by Hermès

DA MAN: Speaking of your long-time collaboration with Marks & Spencer, can you tell us a bit more about how it started and what it entails?
Oliver Cheshire: I’ve been a fan for years. This is something that’s at the heart of British society. My mum shopped there for years; my dad has always shopped there; my nan has always shopped there. I started wearing their clothes and then somebody from the brand said, “Oliver, we’d like to work with you.” So, I started shooting their lookbook and then it kind of escalated from there.

Oliver Cheshire

Swimming trunks by Vilebrequin

DA MAN: We’ve also been going through your blog, IWearTheTrousers.com. Okay, first question about that: Where does that name come from?
Oliver Cheshire: It’s an old saying my dad used to say around the house; it’s kind of like an Old English saying. And I used to get asked that question in interviews: “Who wears the trousers in your relationship?” And I definitely don’t wear the trousers. Pixie does. [Laughs] I just thought it’s a nice twist on words and it kind of fitted. That’s where it comes from.

Oliver Cheshire

Outfit by Hermès

DA MAN: And you mostly talk about style there?
Oliver Cheshire: It’s definitely more about style; menswear is my love. [Through it] I’m trying to teach people and men how to embrace fashion and decipher the runway look. A lot of my friends are saying, “How can I wear that? I’ve seen it on the runway, but it just doesn’t look like something I’ll wear.” It teaches men how to filter out stuff and I also put up the day-to-day things I wear. Just trying to inspire people, really.

Oliver Cheshire

Jacket by Vilebrequin

DA MAN: So, what do you think are the most important menswear styling rules that everybody should know?
Oliver Cheshire: I always say it: read the invite. Dress for the occasion. Men don’t really read the invite. They just put on whatever they want. Women always ask other women what they’re wearing. So, they’ll phone up my girlfriend and say, “What are you wearing tonight?” I think men need to do that more so you don’t feel out of place when you go to a party. Next, get a great tailor. A great tailor will just make wonders for you. Nips and tucks on suits—a suit should always fit perfect. What else? I think, know your color palette, because everyone has different skin tones.

“Women always ask other women what they’re wearing. I think men need to do that more”

DA MAN: How do you deal with the increased public attention? Especially since your engagement to Pixie…
Oliver Cheshire: I just think that you need to have a good group of friends around you; and good agents and obviously management that you trust. I’ve been with Select Model Management 13 years now, and I trust them. I’ve been with them since the beginning. And just don’t change, really. I haven’t really changed. I go to the same places, I see the same friends. I just keep my feet on the ground and enjoy life.

Oliver Cheshire

Outfit by Calvin Klein Platinum

DA MAN: Speaking of things that don’t change, you’re still referred to as “the model with the Midas touch.” Why do you think the campaigns that feature you do so well?
Oliver Cheshire: I think there’s an approachability about me. There’s always been a distance between everyday clothing and high fashion and I want to bring it together. Any man can wear high fashion and I think that’s kind of what brands see in me.

Oliver Cheshire

Jacket by Hermès

DA MAN: You’ve been modeling for quite some time now. 13 years in total, if we’re not mistaken. Where do you see yourself in, say, five years from now?
Oliver Cheshire: That’s a good question. I’d love to go into the magazine industry, do a bit more writing, do some styling, do a bit more creative content, produce some shoots. I’ve been on shoots now for 13 years; I know them inside out, back to front. A lot of the time I’m telling the photographer and the stylist what to do. They hate that. And obviously designing. My passion is clothes and menswear, and just teaching men … no, not teaching them, but giving advice and sharing what I’ve learned. I’ve been lucky enough to work the most creative people in the world for years—I’d like to share that with people.

Oliver Cheshire

Polo shirt by Michael Bastian

DA MAN: If somebody came up to you and asked “How do I become as successful as you?” what would you say?
Oliver Cheshire: First things first, you need to go into the agency. Go straight to the agency and say, “Can I be a model?” They will tell you yes or no straight away. If they can make money out of you, they will take you on. It’s that simple. The next step is to keep yourself looking good, keep yourself looking fit, well-dressed, but not too groomed. You need to be raw-looking and kind of happy-go-lucky. And you need to be able to get changed anywhere. Fashion and male modeling is not glamorous. A lot of the time we’re getting changed in carparks or in the back of cars.

Oliver Cheshire

Top by Calvin Klein Platinum

DA MAN: Outside of work, what else are you passionate about? Do you have any hobbies?
Oliver Cheshire: I’m really into my cycling at the moment. There’s a great thrill to it and good team camaraderie. What else have I been doing? I like to go to the pub with my mates and just enjoy watching football. And traveling. And a lot of shopping.

“There’s always been a distance between everyday clothing and high fashion and I want to bring it together”

DA MAN: Now, you’re originally an East End boy who currently spends a lot of time under the limelight. Do you ever feel out of place ?
Oliver Cheshire: In the beginning I thought it was mad. I never wore designer clothes—I never got the opportunity. I mean, I’m from a working class background. My dad’s a fireman, my mum looked after us. And then all of a sudden getting deal jumpers are in front of me saying “wear this” and “wear that.” Sometimes I look back and think, “bloody hell, this is crazy.”

Oliver Cheshire

Outfit by Hermès

DA MAN: Still, you really seem like a very grounded person. What keeps you there?
Oliver Cheshire: I think it’s my friends around me. They all take the mickey out of me. I go down the pub and they’re like, “What are you wearing that stupid shirt for?” or “Why have you dyed your hair?” And I don’t mind. I think that being with the type of people that can take the mickey out of me keeps me level-headed and grounded. And Pixie’s very level-headed and grounded and we can take the mickey out of each other. I think being light-hearted, being able to take banter and have the mickey taken out of you is fine. I feel like a lot of people don’t like that.

Oliver Cheshire

Jacket by Hermès

DA MAN: Speaking of Pixie, not too long ago you’ve finally proposed to her. Can you tell us a bit about how it went?
Oliver Cheshire: I was getting a lot of people asking me, we’ve been together for nearly seven years. We’re still very happy, we travel the world together, and I thought, this is time, I need to do it. I’ve never bought a ring before, I never proposed to anyone before, so me and my best friend went down to Hatton Garden. We did five minutes of research—we didn’t know anything about diamonds or rings—but I found a ring I thought she might like and bought it. Then I asked her dad to meet me at a coffee shop and I asked him if I could marry his daughter, and he said yes. So, I started planning how to propose. I wanted to do it in another country; I was thinking of New York or maybe Spain or Portugal, or somewhere we go on holiday. And then I spoke to her mum and she so wanted to be there when I do it. That’s when it came to me that I wanted to do it on the steps of St. Paul’s [Cathedral], because I know she loves the church and, you know, we’re both Londoners and it was just special there. So, I had her family around the corner, got some champagne and food, and then I told her we’re going for brunch. I walked up the steps and got down on one knee and asked her to marry me. She started crying and there was makeup everywhere, and she said yes.

Oliver Cheshire

Outfit and sandals by Hermès

DA MAN: And, how are plans going for the wedding?
Oliver Cheshire: We haven’t started planning just yet. I mean, we’ve been pretty busy, but we’re aiming for June or July next year. Haven’t told anyone that yet. [Smiles]

 

Outfit by Marks & Spencer

Outfit by Marks & Spencer

Outfit by Marks & Spencer

Photography: Mitchell Nguyen McCormack
Styling: Peter Zewet
Styling assistant: Primawan Hakim
Videography: Pedro Correa
Location: The Legian Bali in Seminyak and Uluwatu beach.