Now Casting: Oliver Cheshire

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Oliver Cheshire has been modeling for nearly half of his life. After fronting a Calvin Klein campaign that catapulted his career, the British model, who was discovered at 16, went on to star in international ads for the likes of Abercrombie & Fitch and other brands, and continues to appear in numerous editorials. Cheshire stopped by the CR office to talk about travel, trends, and taking a stab at designing.

What is the most exciting part about your job?
Calvin [Klein] and always working with people after a while [who] I haven’t seen in ages. It’s always nice to have the circles come back around and to see familiar faces and old friends in the industry, like Luke Day, who I worked with when I was younger and then did another shoot with 10 years later. It’s always fun to see how paths cross and intertwine again.“

What is your favorite thing about modeling?
„Probably what everyone else says: the traveling. I love coming to New York. It reminds me of London, the hustle and bustle.“

What do you like to do in New York?
„I like to rent a bike and go around Central Park. It’s always quite fun. And obviously eat Mexican food. There’s such good Mexican food in this city. Yeah, that’s my jam.“

Do you have any men’s style tips?
„Always read the invite info about what the dress code is. That’s one thing that guys don’t normally do. It’s always good to know if it’s black tie or not. And don’t pick up a fashion magazine and read the full trend list and try them out all at the same time. Try one or two, but not all of them or you’ll look like a bloody idiot.“

What trend are you currently into?
„I like the Western trend. I’ve got a few cowboy shirts, but haven’t got my cowboy hat yet. That’s a bit much.“

What’s your go-to drink order?
„My drink order at the moment is a Moscow mule.“

How do you prepare for a shoot?
„Don’t drink too much the day before. I’m not a teenager anymore, so I can’t do that unfortunately. I just try to get a good night’s sleep and keep the wrinkles at bay.“

When you’re on a shoot, how do you set the tone?
„I don’t like a set to be silent. I like a fun team, you know, [where] no one that takes themselves too seriously. We’re very lucky to do [the] job that we do.“

What are you looking forward to at the moment?
„I’ve got a [menswear] label releasing, my own brand, which is quite exciting. I’ve been working on it for a year now and it’s called Che. We’re starting with resort in the beginning and then will [move] on to other things, but it’s an evolving studio and very trend-driven. It’s aspirational, so not too expensive and not too cheap. It’s fully eco as well. I wouldn’t say that I’m an eco warrior, but when looking for ways of doing things, the materials that were eco were so amazing and as good as the non-eco-friendly ones, so why wouldn’t you use them? With all of the information that we have today about what we’re doing to the planet, why wouldn’t I go down that line?“

What inspired the style of the brand?
„I’m using a lot of ‘60s NBA and a bit of French Riviera as well, like tailored and luxury. I want to design for my friends, basically. I shot the campaign in the south of France with all of my friends and called in some favors with some of the big guys.“

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