This is a weird thing to say but, if you ever get the chance, I strongly recommend watching a supermodel get dressed in the morning. Oliver Cheshire has a small but attentive audience on set as he picks out looks for today’s photoshoot. He’s styling it himself, as busy behind the camera as he is in front of it.
The theme: enduring warm-weather classics, most of them from the middle of the 20th century. “It does put you in a good mood, summer dressing,” Cheshire says, leafing through a rail of colourful open-collar shirts, linen suits and resort wear. “It’s a relaxed style of dressing. Very easy.”
Easy? That’s not a popular opinion when it comes to men’s summer clothes; there are too many banana skins. Are the shorts too short? Is my skin too pale? Is the shirt too loud? Do I look like a prat in a hat? Cheshire’s mission today is to show that summer style is no sweat – you can be colourful, bare your skin, do unspeakable things to a suit and still look cool under the glaring sun.
It helps, of course, being Oliver Cheshire. One of the world’s most recognisable male models (and quite possibly the nicest guy in menswear), Cheshire’s decade-long career includes regular walks for Dolce & Gabbana and campaigns for Calvin Klein and Hugo Boss. Closer to home, he’s a regular face of Marks & Spencer’s menswear range, and has just launched his own label.
More on that later because he’s getting dressed again, and it’s worth paying attention. Watching Cheshire pick out clothes, you realise a couple of things. 1) Yes he does look Photoshopped without a top on. 2) The reason he can wear so many different looks isn’t just the abs or the one-percenter bone structure. The man’s a scientist of style.
At work, he rearranges clothes on the rack in front of him, studies them, picks out new combinations. The process is part-experimentation, part-instinct. Cheshire creates outfits like a chef concocts recipes, mixing ingredients that you don’t think would work together but of course they do.
“I’m very into it,” he admits. “I’m always looking at the menswear shows and when you take an interest in anything, you understand it.”
He started young. He learned to sew as a teenager, customising his clothes so that they were all one-of-a-kind. “I’d cut the tab out of the back of my Levi’s, then cut a hole at the front and sew it in. My mates were always taking the piss.”
Today, he’s a walking Wikipedia of menswear, which is probably why his style is so eclectic. At FashionBeans, we once described him as the “bastard who looks good in anything”. We stand by it. He’s pristine in a tux, but wore snakeskin cowboy boots to the Brits and made them look good. He does camp short shorts and hard-to-wear prints, and mixes sportswear and tailored pieces better than anyone we know.
He’s also a magpie. More than once during the shoot he fires up Pinterest for inspiration and admits that a song he hears on the radio can decide what he wears that day. “Music and films really do influence the way I dress. I can listen to rock n roll music in the morning and want to put a leather jacket on. If I put a rap song on, I’ll be walking out of the house in a pair of trainers and a hoodie. It’s weird.”
On set today, we’re listening to Buddy Holly, Little Richard and Jerry Lee Lewis. There’s a hazy late ’50s vibe and, in front of the camera, Cheshire is dressed for it. The rails are full of mid-century summer gear – his favourites are a knitted button-through polo and a striped open-collar knit – classics that look as good in the sun today as they did half a century ago.
“It was one of the most stylish eras of American history,” Cheshire says. “And it went everywhere because that was really the first time fashion was so visible, so heavily documented.” This was the birth of youth culture, of television and the emergence of the world’s first global style icons, people like James Dean and Elvis Presley.
“When they first appeared, they dressed in a way that anyone could copy. It was the first time men could really enjoy casual dress and use it to rebel. And it’s not scary. Even if you’re not hugely into menswear, it’s easy to throw on a pair of jeans a white T-shirt and a bomber jacket. And these looks can be redone in so many ways.”
Case in point: Cheshire’s new label, Ché. It’s a small but brilliant collection of resort wear, a bullseye example of how to dress well when the sun’s out. It’s retro but modern, tailored but comfortable, colourful but elegant, simple but also very smart. The swim shorts are made from an eco-friendly nylon made out of reused fishing nets while the shirts – which are often part of a matching co-ord set – are cut from soft, breathable viscose.
Inspiration came from a few places but one of them was mid-century America. “I really love ’50s and ’60s NBA,” he says. “All the colours, the shapes, that retro feel – but with modern cuts so they’re more wearable. I also wanted to use really rich colours – deep dark oranges, pinks – and show men how to use them.”
The kid who used to cut up his Levi’s has always wanted to produce his own menswear label, but turning 30 in 2018 gave Cheshire the impetus to finally get Ché off the ground. He helped source the materials, created extensive mood boards and marshalled a team not just to produce the clothes but create a website, build a marketing campaign and a pop-up shop. “I wanted to understand the whole process,” he says.
Cheshire is maturing. He’s planning his wedding to singer Pixie Lott, who might be the only person who gets a say in how he dresses. “Oh yeah, she hates me in vests,” he says. “She’ll see me wearing one and be like, ‘Get that bloody thing off. You’re not wearing that out, are you?’ She’ll tell me if I go a bit much with a look. She’ll say, ‘You look a bit …wacky.’”
Cheshire is obviously a confident dresser but says he can feel his style evolving as he gets older. “When you’re young you experiment with style. You dip your toe in, not really knowing what suits you. I do find myself wanting to make a nice impression and just feel like an adult.”
He pauses. “But I still love to experiment and I’m never going to be the kind of person to just wear a suit for the rest of my life. That’s what clothes are about, aren’t they? It should be a pleasurable thing, getting dressed.”
Oliver Cheshire’s 7 Summer Style Rules
Go Easy On Trends
“I always look at trends,” Cheshire says. “I’m interested in them and where they come from. But I don’t believe in trying them all out. They should be happy accidents. If baggy trousers are in, that doesn’t mean you change your whole wardrobe so you can wear more baggy trousers.”
And you can change your mind. For years, Cheshire bared his ankles with summer trousers but he’s had a change of heart. “I was always no socks, now I’m all for them. Love a white sock.”
Rethink The Summer Suit
“Tailoring will never go away but suits have become less structured. You don’t have huge shoulder pads weighing you down. It’s almost sporty. They almost turn into a tracksuit, and that’s what I think a modern suit should be.
“M&S has got amazing linen blend suits at the moment that come in pastels. They don’t crease as much, they’re soft shouldered. I wear them to Wimbledon, the polo but they’re also good to mix and match. You can take the linen trousers and wear them with, say, a tucked-in T-shirt and a pair of trainers. Easy to dress down.”
You Can Be Smart Even At The Pool
“I love tailored swim shorts,” Cheshire says. The ones he designed for Ché are comfortable with an elasticated waistband because who doesn’t want to relax on holiday? But they’re also cut straight and clean, finishing at the mid-thigh.
Wear them with sliders at the pool, he says, leather sandals everywhere else.
Be Colourful, Not Garish
There are a lot of loud prints and eye-popping colours in shops at the moment. Cheshire thinks it’s a good thing, but also offers a word of caution. “A colourful Hawaiian shirt is great, but don’t go too colourful. Something wearable, you know what I mean? Muted greens and blacks. Blood red.”
Avoid The Tourist Traps
“Men always go straight for beige trousers in the summer but there are so many nicer colours you can try,” Cheshire says. “Stone is a much more modern way of doing it.”
He’s also a fan of linen trousers, which have a bad rep. “Yeah, they were bad because they used to crease so easily. Now there are new materials about that make them breathable. One hundred per cent amazing. Linen blend trousers are the one you want.”
Pick The Right Pattern
There’s a whole menagerie of prints and patterns in menswear this summer, from crazy florals to snarling leopard print. They’re all eye-catching, but Cheshire prefers one that actually flatters you. “I really like vertical stripe T-shirts – been wearing them a lot lately. They elongate the body.”
Always Read The Invitation
“I definitely dress for events,” he says, and especially in summer. “Weddings, Wimbledon. I always dress for occasions, always. Read the invite. I want to fit in but at the same time, I want to feel elegant there. It’s that classic thing – you put on the right suit and you just feel good.”
Styling: Oliver Cheshire
Photography: Simon Lipman
Photographer’s assistant: Kai Gurung
Digital assistant: Gemma Gravett
Art direction: Luke Sampson
Fashion assistant: Richard Jones
Grooming: Shauna Taggart & James Harknett