15 Excellent Outfits To Steal From Oliver Cheshire

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. So how has he managed to pull it off?

The Look

Well, Cheshire realizes that relatable style needs to be adaptable and versatile, with a strong outfit available for every occasion. Expect well-fitted suits with a natty check for when fashion week rolls around and a simple, clean tracksuit under a winter coat for when he has just rolled out of bed on a Sunday morning.

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 Mr. Ripley

Go-To Brands: Marks & Spencer, Dolce & Gabbana, Dior

Follow Him: @oliver_cheshire

Hug a Hoodie

The likelihood is you only ever chuck a hoodie on around the house, dare anyone out of its confines see you in one. But Cheshire wears his with pride and so should you by ensuring it is plain and unbranded and kept timeless in a fresh, basic 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 bang on the ‘high-low’ trend.

Oliver Cheshire Wearing A Hoodie And Shorts

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. Here it comes in the form of a crustacean patched onto the shoulder of a racing green field jacket he wore to Haute Couture Fashion Week in Paris.

It shows his ability to bring a touch of high fashion to a look you can pull off at home, mainly by employing it with an all-black uniform of roll neck, jeans and Chelsea boots.

Oliver Cheshire At Haute Couture Fashion Week

Paint Factory Explosion

Having a job that sees you permanently fixed onto the front row of every major fashion week means Cheshire can always stay on trend. Here we see him showing off the paint splatter as showcased by menswear designers Phillip Lim and Junya Watanabe.

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.

Oliver Cheshire Wearing A Patterned Suit

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. Good-quality jeans should always have a place in your wardrobe and turning them up prevents unwanted bunches at the hem while also showcasing any edgy footwear you may be sporting. Upstairs, a floral shirt can really make an outfit pop under a more demure jacket while a vest under the shirt is useful on uncertain spring days.

Oliver Cheshire's 15 Best Outfits

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 takes with just the brand name or logo work best (like the Nike swoosh). To smarten the look do as you would a collared shirt – tuck into tailored trousers with an elegant side stripe to keep the sporty feel going, and wear with smart shoes sans socks.

Oliver Cheshire Wearing Athleisure

An All-Grey Tracksuit Day

It might be a bit Goldie Looking Chain, but in the hands of a style pro like Cheshire, the all-in-one tracksuit can actually 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. An upturn can also prevent joggers looking sloppy at the bottom, while clean white trainers work with everything.

Oliver Cheshire Wearing A Tracksuit And Overcoat

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. Then you have a shearling trim on the pea coat, with a denim jacket underneath. The sharp fit on both means Cheshire gets away with it. The look is completed with the greatest tool in every layering arsenal – the black roll neck.

Oliver Cheshire Wearing A Shearling Coat

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. Matching the color, but in a different shade, is a nice play for a piece this extravagant. Plus, any leather jacket is going to work tidily with black skinny jeans and polished Chelsea boots.

Oliver Cheshire Wearing A Blue Biker Jacket

Chunky Knit

Now beware of the chunky knit under the bomber jacket. If you don’t have the abs of an Adonis a la Cheshire then you risk looking like the Michelin man. But if your frame could be best described as slight, hop 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.

Oliver Cheshire Wearing A Cream Roll Neck

Statement Bomber Jacket

Another glamorous fashion week after-party, another statement jacket to dazzle all those 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.

Oliver Cheshire Wearing A Patterned Bomber Jacket

Tux Luxe

The grandaddy of menswear, the tuxedo is powerful if pulled off, hideous if not. If you go the way of Cheshire and choose a three-piece for your black tie event, make sure the waistcoat is covering your trousers band seam, so there are no unsightly flaps or unwanted rolls of white shirt peeking through. Also, keep the jacket buttoned up unless you’re seated – you’re after the secret agent look not a mobster on the run.

Oliver Cheshire Wearing A Dinner Suit

Dashing Suit? Check

The checks and stripes and whatever else is going on in this suit are making us, sorry what, spaced out a bit there. 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.

Oliver Cheshire Wearing A Grey Check Suit

Bringing 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. Works well with light brown suede boots too.

Oliver Cheshire Wearing A Poncho

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 style works best in a floaty fabric like the jersey Cheshire opts for here. 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.

Oliver Cheshire Wearing A Cuban Collar Shirt

Earning Your Pinstripes

The wide lapel pinstripe suit is synonymous with the world of banking, coming about because all the Gordon Geckos and Patrick Batemans wanted a suit that would stand out from the crowd. As a consequence, the suits became rather comical, so today the look works best without any unnecessary embellishments. A simple, yet bold tie and a slimmer fit in the trousers will modernize all that 1980s yuppiness.

Oliver Cheshire Wearing A Pinstripe Suit

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