Often seen grinning like a Cheshire cat, model and blogger Oliver Cheshire doesn’t come across as your bog-standard Zoolander male model. Yes, he can pull out the killer pout at an instant, has the pop star fiancé (singer Pixie Lott) and the cheekbones sharp enough to cut diamonds, but London-born Cheshire’s ace up the sleeve is his ability to come across as an approachable everyman with an outfit for every day.
It’s meant that he has been able to successfully bridge the gap between high fashion – cavorting down the catwalk for Dolce & Gabbana or modeling underwear for Calvin Klein – and high-street fashion as one of the faces of Marks & Spencer. How has he done it?
The Look
Cheshire understands that relatable styles need to be adaptable. He has a great outfit for any occasion. You can expect well-fitted suits in a stylish check when Fashion Week rolls around, and a clean tracksuit underneath a winter jacket when he just got out of bed.
If Cheshire does want to make a statement it is usually with a jacket or a shirt (if it’s a shirt, then the jacket is muted). Footwear is simple but elegant – Chelsea boots in black or brown suede, clean chunky trainers, and dainty dress shoes – almost always without socks. #FreeTheMankle.
Inspiration: David Beckham, Ryan Gosling, The Talented Ripley
Go-To Brands: Marks & Spencer, Dolce & Gabbana, Dior
Follow Him @oliver_cheshire
Hug a Hoodie
You probably only wear a hoodie around the house. Dare anyone to see you wearing one. Cheshire is proud to wear his hoodie and you should be too. Make sure it’s plain, unbranded, and in a timeless color.
Hoodies are also designed for comfort so take after Cheshire and invest in a soft cotton piece and combine it with either tailored trousers or, as he’s done here, a collared shirt, for a look that is
Safari Under The Sea
It’s rare for Cheshire to make a style misstep, but you can’t accuse the model of playing it safe all the time, as he is often seen switching up his style with idiosyncratic touches that are all his own. The model wore a jacket with a racing-green field and a crustacean sewn onto the shoulder.
This shows how he can bring a little high fashion into a look that you can do at home. He does this by using an all-black outfit of jeans, roll necks, and Chelsea boots.
Paint Factory Explosion
Cheshire is always on trend because he’s always in the front row at every major fashion show. Here he is displaying paint splatters as seen by designers Junya Watanabe and Phillip Lim.
We agree the trend is a bit walking talking Jackson Pollock, but Cheshire works it by making sure the suit has no break on the trouser hem or bunches on the shoulders – high fashion needs to fit like it was made for you.
A Floral Flourish
While we can’t imagine everyone pulling off the paint splatter like Cheshire, here is a look we feel most chaps should observe and repeat. A pair of good-quality jeans is a staple in any wardrobe. By turning them up, you can prevent any unwanted bunching at the hem. This also allows for a better view of your edgy shoes. Under a modest jacket, a floral top can make an outfit really pop. A vest is a great addition for spring days.
Just Do It
Instagram culture has brought the logo tee back into style – it’s the easiest way of telling people where you got your shirt after all. Simple designs with only the logo or brand name work best.
An All-Grey Tracksuit Day
The all-in one tracksuit might look like a Goldie Looking Chain but, in the hands a style expert such as Cheshire, it can work. First of all, make sure it’s clean – food stains will never be chic but are even more unforgiving when dressing down – and wear as a layer under a slim-fitting winter coat. A slight upturn will also make joggers look neater at the bottom. White trainers go with anything.
Layering Mastery
There’s more than meets the eye in this outfit that, from a distance, looks cool and understated but on closer inspection paints a rather more busy picture.
First, there are the white jeans – never an easy look – which is turned up so there’s no bunching and counterbalanced by darker colors up top. You can see a shearling trim at the bottom of a peacoat, and a denim jacket on top. Cheshire is able to get away with it because of the sharp fit. The look is completed with the greatest tool in every layering arsenal – the black roll neck.
Mr Blue Sky
One of the many cool jackets in Cheshire’s portfolio is this marvelous breezy blue leather creation. Have it stop around your hips and as close to being in unison with the hem of your shirt, while it shouldn’t be so oversized that the shoulders droop off at the sides. For a piece as extravagant, it’s nice to match the color in a slightly different shade. Any leather jacket will look great with black skinny jeans, polished Chelsea boots and a blazer.
Chunky Knit
Watch out for the chunky sweater under your bomber jacket. If you don’t have the abs of an Adonis a la Cheshire then you risk looking like the Michelin man. If you have a frame that could best be described as small, jump on board. Just make sure you’ve got something going on – in this case, the multi fabrics on the jacket and the cable knit of the jumper – or you risk blending into the wall.
Statement Bomber Jacket
A glamorous after-party for fashion week, and another statement jacket that will dazzle everyone in attendance. A slim cut and silky bomber jacket with black cuffs fits well with lightweight smart trousers and Cheshire’s favorite pair of woven black shoes. Then it’s a snug white tee, tucked in, and the smart casual dress code has been well and truly smashed.
Tux Luxe
The tuxedo can be powerful, if worn correctly, or hideous, if not. If you’re going the Cheshire route and choosing a three-piece suit for a black tie event make sure your waistcoat covers your trousers band so that there aren’t any unwanted flaps or rolls of white shirt showing through. Also, keep the jacket buttoned up unless you’re seated – you’re after the secret agent look not a mobster on the run.
Check out this Dashing Suit! Check
We’re a little distracted by the stripes and checks in this suit. If you’re going for a piece that is so optically hypnotic you absolutely have to tone everything else down. Simple but hip, the grey knitted tie embellishes the suit jacket and a white shirt won’t cause any headaches. And here’s the proof that brown shoes can go with (light) grey.
Bring Back the Poncho
This jumper might have some worrying ‘backpacking around Peru on the gap yah’ vibes, but Cheshire miraculously pulls it off with a not-outrageous color scheme. We like how it is kind of matched with the gold watch and you can wipe that bead of sweat from your forehead because light wash denim is cool again, as long as it’s relaxed. Also looks good with light brown leather boots.
Cool as a Cuban
The closest we get to Havana nights in this country is the sweaty, heaving queue for the bar on a Friday after work, but it’s not stopped everyone from jumping on the Cuban collar shirt. The Cuban collar shirt looks best on a floaty material like the jersey Cheshire chose. If you’ve got anything resembling guns have the sleeves cut to mid-bicep and tuck the shirt into a smart pair of plain smart trousers to properly unleash the V.
Earning your Pinstripes
The pinstripe wide-lapel suit has become synonymous with the banking world. It was created by all the Gordon Geckos who wanted a suit to stand out. Due to this, suits began to appear comical. Today, it is best not add any extra embellishments. Modernize 1980s yuppiness with a bold, simple tie and slimmer pants.
