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Oliver Cheshire Talks Life as a Male Model to DA MAN Style FW16

LONDON CALLING. Some male models pose for a living, others for passion for fashion. Belonging to the latter is Londoner and male modeling poster boy Oliver Cheshire, who currently also dabbles in writing and fashion design


Oliver Cheshire for DA MAN Style FW16 in outfit by salvatore Ferragamo
Outfit by Salvatore Ferragamo


With menswear now enjoying an ongoing rise in the fashion industry, the male modeling trade is slowly but surely revealing its long-dormant power. Oliver Cheshire is among a select few who have been able to churn out a sharp increase in sales for brands whose campaign he fronts. What sets this Londoner further apart from his peers is his dedication to fashion, which extends beyond the sphere of modeling.

The 28-year-old is often spotted in handsome sartorial ensembles on a day-to-day basis, blogs about men’s style and now has a hand in fashion designing. The fact that he’s been modeling for more than a decade only adds weight to whatever he says and, well, wears. Surely, he’s not afraid to show it.



DA MAN: Hi Oliver, thank you for making time to chat with us. So, how are you doing and what are you currently busy working on?
Oliver Cheshire: I’m doing very well. Thanks. I’m currently working on my personal website/blog,, which is a style and travel blog, with a mixture of things I get up to!

DA MAN: How’s 2016 shaping up for you?
Oliver Cheshire: Bloody great!

DA MAN: Any big projects coming up for the rest of the year?
Oliver Cheshire: I’m still working very closely with Marks & Spencer, which is always exciting. I’m also experimenting with designing a clothing brand at the moment—a smart casual brand that will show men a new way of dressing. That’s all I can say at the moment. So, keep watching this space!


Oliver Cheshire for DA MAN Style FW16 in outfit by lanvin, lapel pin by Kasun
Outfit by Lanvin, lapel pin by Kasun


DA MAN: You were scouted at a very young age when you were studying drama. What was it that made you confident to pursue modeling?
Oliver Cheshire: I always dreamed of acting from a young age. But once I started to become so busy in the fashion industry, I thought I would be silly to go against the tide and pursue something different. All the travel and meeting of new people made me realize modeling was for me.

DA MAN: One of your first big campaigns was for Calvin Klein. How did the project land on your lap? And now, looking back, how do you think has the experience helped you as a model?
Oliver Cheshire: Within a month of being signed by Select Model Management and having had only shot some Polaroids, I was asked to cast for Calvin Klein in New York. I was told I didn’t get it, as I looked too young next to the female model. The next thing I know I had another phone call saying I had to fly to L.A. to test with her, and the rest is history. I guess, looking back now, it was a massive platform for me and my career took off straight after that.

DA MAN: Who did you look up to when you were still new to modeling?
Oliver Cheshire: Tyson Beckford was, and still is, a huge icon in the industry and probably one of the first male models to become a brand within himself.


Oliver Cheshire for DA MAN Style FW16 in Coat by lanvin
Coat by Lanvin


DA MAN: You’ve been in the industry for more than a decade now. What are the highs and lows of being a male model?
Oliver Cheshire: The highs are never knowing what’s what—jobs and career moves are just around the corner. The lows are always waiting around for things to happen and being on the move, missing family get-togethers and friends.

DA MAN: Some brands mentioned that they had a sharp increase in sales following their campaigns featuring you. Have they ever discussed this with you?
Oliver Cheshire: Since I was young I always have had a passion for dressing well and taking pride in what I wear; so I feel that is reflected on the images I work on. I also always have people come up to me and ask me what I’m wearing on the streets and on social media. So, I feel this may be the reason for their increased sales.

DA MAN: What makes a male model successful, in your opinion?
Oliver Cheshire: By being happy with what you are doing and also being creative and having a good personality.

DA MAN: Is being active on social media also important for your career?
Oliver Cheshire: It is now with the rise of social media stars and Instagram models. Casting directors now ask how many followers people have before booking them.


Oliver Cheshire for DA MAN Style FW16 in Outfit by Vivienne Westwood
Outfit by Vivienne Westwood


DA MAN: Have you ever thought of going back to pursuing drama? Or perhaps trying out for, say, a singing career?
Oliver Cheshire: I can’t sing but I’m great at playing the tambourine. [Laughs]

DA MAN: You always look ripped and fit. But surely you have some guilty pleasures you occasionally indulge in…
Oliver Cheshire: Chocolate and pizza at the same time. [Laughs]

DA MAN: Lastly, do you have a favorite quote that’s always stuck in the back of your mind?
Oliver Cheshire: The entire British Empire was built on cups of tea, and if you think I’m going to war without one, mate, you’re mistaken! [from “Lock, Stock and Two Smoking Barrels”]



To see more exclusive images from this shoot, get your copy of DA MAN Style Fall/Winter 2016 here, and check out these outtakes below:


OUTTAKE - Oliver Cheshire for DA MAN Style FW16 in outfit by gucci
Outfit by Gucci


OUTTAKE - Oliver Cheshire for DA MAN Style FW16 in outfit by Chalayan
Outfit by Chalayan





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