How To Get Oliver Cheshire's Style

Oliver Cheshire – aka David Gandy‘s model BFF – is one of Britain’s biggest of-the-moment style icons.

Now 26-years-old, Cheshire was scouted age 15, whisked straight off to New York, and became an overnight success as the new face of Calvin Klein.

His Adonis face has since fronted Dolce & Gabbana, Missoni and Abercrombie & Fitch, before pictures of Cheshire in M&S swimwear went viral; the model’s eight-pack physique and olive skin making the trunks look so good the retailer’s sales rose by more than 50%.

Men want to look like him, and women want to be with him (ignoring the fact he’s indeed dating Pixie Lott). But Cheshire, like the flamboyant cat from Alice In Wonderland, is a man of cryptic qualities, hidden behind one mischievous grin. Luckily for us, his style is a little more readable. But, just who cuts his incredible hair?

Breaking It Down


Cheshire favours the look of the timeless gent – think James Dean, Paul Newman and Marlon Brando – meaning he is forever working simple, retro-looks that most guys wish they had the charisma to pull off.

From the tonal blue outfits to shearling coats and Chelsea boots, most of Cheshire’s slick combinations are more accessible than you think; especially due to the fact he mixes high-street brands with more luxury labels.

His suiting is minimal and classic and doesn’t boast modern eccentricities, so it’s a win – whatever the occasion – from the office to weekend wedding. Clean and polished, Cheshire returns the man to his masculine heritage with classic good-looks and pared-down essentials.

Oh, and his hairdresser’s name is Larry (true story), and he works at London’s Daniel Hersheson. Book in.

All-Blue Everything


Blue makes the boy. And Cheshire blends the signature masculine colour into a superb tonal look. It’s an incredible way to address tailoring, starting with the indigo chambray shirt or powder blue Oxford and working outward from there.

Layering works with a cashmere blue cardigan or blue tweed waistcoat, followed by a midnight blue Harrington and matching trouser.

For day suits, take a micro-check greyish blue suit, add a blue tee (stripes or not) and whack on a pair of shades for a summery suit feel. Brogues in tan pop lively on the blue and lose the belt to retain the chilled attitude.

Retro Prints


Mr. Cheshire has a taste for bold, all-over prints – styling to create an attractive focal point as part of his casual ensemble. Retro stripes, fern motifs and architectural geo’s are common patterns and – just like Cheshire – aim to pick just one stand-out piece to for patterning like the button shirt. In short sleeves, the Fifties ‘work shirt’ boasts a sprawled collar for a pared-down elegance, that needs a print for it to feel complete.

Let the shirt do talking, opting for neutral wardrobe staples to accompany the chatter. Khaki chinos, and indigo or black jeans offer casual timelessness. Or, work the shirt into a casual and formal combination, opting for a light grey suit and open neck, for easy matching that feels a touch vintage. Now, chuck on some retro sneakers or loafers (no socks) and roll the pant cuffs for that extra kick.

Slim & Single


Tailoring is effortless for the man with the perfect bod. But Cheshire still proves he knows what he’s doing, keeping things slim and simple; back to basics. Reneging on bold prints for suits, follow Cheshire’s line with a classic neutral colour palette sticking close to grey, navy and camel. The most adventurous the model gets with colour is blue, never deviating for the cobalt or slight electrics that are on trend right now.

Accessories are more bold in comparison, opting for silk knit long ties (never a bow) for texture against the sleekness of the single-breasted woollen. The white handkerchief is his go-to, as opposed to an outlandish pocket square, sitting pure and crisp like the sleeve cuff of his neatly pressed Oxford shirt. Leather Derbies are everything in brown and tan, with the odd sneaker bouncing on in for an athleisure take on tailoring.

Rock N Roll


A style rebel, Cheshire is all about the rock and the roll. Cheshire takes the smooth Seventies high-neck knit and slots it under an aviator jacket in suede for a night and day look that boasts rockstar finesse. The fine-gauge knit drips sophistication, with Euro-chic neutrals such as tan, black or grey.

Now to the coat. Shearling collars and lining, which offer a fleecy, plush look for winter, are super on trend and Cheshire models well the versatility of this look. A pair of tailored trousers and double-monks are a smarter version of the rock ‘n’ roll, but nothing beats the slim-fit black denim and Sixties Chelsea boot with matching leather belt to carry you through into the musical night.

Key Cheshire Fashion Items

Suit: Something British like Hackett London and Hawkes & Gieves for custom-made. M&S and Topman for something very affordable and off-the-rack.

Outerwear: H&M for casual jackets, suede shearling coat from Coach and Burberry trench. Grab a Chesterfield coat for Aquascutum.

Tops: River Island and Zara for white button-downs and Paul Smith for retro print shirts. Denim shirts and cardigan from Uniqlo.

Bottoms: Swimwear are Orlebar Brown, chinos are from J.Crew and Uniqlo, and trousers are from Topman. Jeans come from Dr Denim.

Shoes:  Leather lace-ups from John Lobb or Grenson and sneakers from Jack Purcell.

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