Oliver Cheshire Almost Became a Fireman Before He Was Scouted to Model

Hugo Boss Artemis Challenge Race Oliver Cheshire — Oliver Cheshire Lloyd Images

In between dodging raindrops and working as a crew member on the “Hugo Boss,” a carbon-fiber IMOCA 60 boat that took part in a charity race off the Isle of Wight on Thursday, Oliver Cheshire talked to WWD about his favorite suede jacket, his obsession with Air Max sneakers and an unexplored career path as a firefighter.

WWD: How would you define your style?

Oliver Cheshire: Preppy, rock ’n’ roll and sports luxe. I think I take a little bit of each of them. The most important thing is to dress for the occasion, to know the occasion. I’ve turned up to things and felt so out of place, so dress for the occasion has to be on point.

WWD: Do you have a favorite item of clothing?

OC: My Hardy Amies’ suede jacket. Basically, I met the designer in Pret (A Manger). It was a random meeting and he just said: “I would love to dress you for one of the days of London Collections: Men.” I just loved all the items in there and I saw this suede jacket and I wore it and fell in love with it.

WWD: What is your go-to look?

OC: A tailored pair of trousers. I like to be comfortable when I’m on the move, so I’m usually wearing trainers, and then a shirt or a jumper, I’m more of a shirt/jumper kind of guy.

WWD: Do you collect trainers?

OC: I love trainers, yeah. People want to wear trainers, they want to be comfortable, they want to look stylish — and we’re on the go constantly.

WWD: Do you have a favorite pair?

OC: Air Max, Air Max 1. And then obviously a classic, Stan Smith.

WWD: What do you when you’re not working?

OC: Movies, films, lots of sports, I like to play football, swimming…chill with my mates. I don’t get to see my mates that much, because I travel so much. See my girlfriend (Pixie Lott, the singer, songwriter and actress), go for dinner, I love food. I love cooking, actually. Goose, fishes, everything really. Lasagna, loads of Italian.

WWD: Are there any standout modeling moments?

OC: When I got scouted I was 15. They flew me to New York, I was meeting shoe designers who booked me, and that changed my life. I was going to be a fireman like my dad. It changed everything.

WWD: So if you weren’t modeling you would be a fireman?

OC: I think so, yeah. I was studying drama, but I was from a little town, and obviously you can’t rely solely on a dream, you know. But I always loved acting and films.