How to Dress like Street Style Icon Oliver Cheshire

oliver cheshire how to dress
Oliver Cheshire | PHOTO CREDIT: Hugo Boss

Easily one of the best dressed men in Britain; Oliver Cheshire’s contemporary, stylish flair is admired by many-a-man. Check out our complete guide with tips on how you can replicate his simple, yet timeless style.

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As one of the illustrious LCM ambassadors, a FROW regular, the face of M&S Autograph Collection and the body of Hugo Boss; it’s little wonder Oliver Cheshire has just under 90,000 followers on Instagram, style columns with both GQ and The Telegraph and beautiful a pop star girlfriend on his arm in the shape of Miss Pixie Lott.

The allure of Cheshire’s style is in it’s simplicity, and while we accept that his high-end looks aren’t always achievable to the average man, the fundamentals can easily be replicated. Here at The Idle Man, we recognise a stellar clothes horse when we see one, and as such, have put together a complete guide on all you need to know to get the model of the moment’s look.

With a rippling set of abs and cheekbones that could cut glass, we can’t promise you’ll be getting quite the same amount of attention as the London-born Adonis, but we can certainly help you try…

How to Dress like Oliver Cheshire

Smart Suiting

A fan of tailoring in all its forms; Cheshire is known to dial it up for black tie events with a patterned blazer, but in typical sartorial chameleon style, is just as likely to show up in a minimal grey tweed option – accessorised in all the right ways, of course.

When it comes to smart suiting, he’ll will always knock it out of the park, however; when attempting to replicate one of his looks, it’s important to remember that we’re not all blessed with model proportions.

Some cuts, as we all know too well, just don’t work for every body type. The best way to get around this would be to opt for a slimline suit. A slimline suit is the flattering option for most body types. For a more modern take on tailoring, ditch the tie or wear with a fine knit.

oliver cheshire navy suit mens street style
Oliver Cheshire weaing a patterend navy suit and a striped T-shirt men’s street style


Casual Leather

For casual looks, our style hero tends to go for classic jackets. A black leather biker jacket over a simple tee or a roll neck exudes rebel appeal and Cheshire pulls it off like no other. It’s easily one of the simplest of Oliver’s looks to pull off, presuming you’ve got a leather jacket at your disposal. If you’ve not yet added this wardrobe essential to your arsenal, come on now? Really?

Marlon Brando and James Dean most certainly were symbols of sex and youthful rebellion, however the black bikers they donned in two of cinema’s most iconic roles only emphasised their inherent coolness. In fact, one might argue that it was they who gave the biker its rebellious sex appeal, not the other way round, so go for one only if you can wear it with confidence.

oliver cheshire leather biker jacket polka dot shirt black jeans mens street style
Oliver Cheshire wearing a black leather biker jacket with a polka dot shirt and black jeans men’s street style


Smart Casual

While Oliver is best known for his smartly executed tailoring looks and high-end, smart casual wear; when the dress code deems it acceptable, he’s just as likely to roll up in some dressed down outerwear. While those cheekbones could certainly compliment and carry almost any outfit off with ease, the recent movement towards practicality and functionality while maintaining style merit makes the below outfit an acceptable level of dressed-down for a more laid-back event.

A white denim jacket or denim overshirt will work perfectly for a more smart-casual look, and to add something a little smarter then why not try wearing a pair of navy chinos and either a smart pair of trainers or a more formal shoe.

Oliver Cheshire wears a white denim jacket
Oliver Cheshire wears a white denim jacket



With the rise in sports and leisure wear becoming acceptable as alternatives to smarter options, Oliver championed the look to perfection when attending fashion week a couple of seasons back. Hoodies over the past few seasons have been on the rise with several desginers bringing out a few pricey versions of this comfortbale staple.

Worn under a coat or a jacket, the humble hoodie transforms into something extremely stylish. The trick is to not put too much effort into what you’re wearing; have an air of nonchalance about you and you’ll be able to pull this look off with ease.

oliver cheshire brown suede bombber jacket grey hoodie mens street style
Oliver Chesshire wearing a brown suede bomber jacket and a grey hoodie men’s street style


Technical Rainwear

While we all love to see a light spring / summer ensemble from time to time, it’d be uninformative of us not to include a few options for the wetter weather we’re all used to dressing for in the UK.

While the odds are stacked against you in an almighty downpour, with a little careful consideration you can maintain your style merit even when the skies open up (we can’t teach you how to keep your hair in one piece, unfortunately). Just because it’s raining doesn’t mean you have to compromise on style. Here we see Oliver Cheshire spoting a tailored grey suit and a white suit with absolute ease; a constant classic, the grey suit works harmoniously with the colourful rain coat over the top.

Oliver Cheshire wearing a grey suit
Oliver Cheshire wears a grey suit with black shoes
PHOTO CREDIT: New York Times


Summer Suiting

Casual, light summer suiting is a great option for work in the summer, a day about the city with friends, or even something a little more formal, such as a wedding. Opt for a lighter material such as linen or cotton, ideally in a lighter colour also so you’re not attracting the heat.

Mixing your suit with a simple white t-shirt, as Oliver has done below, is also a great way to get more from your suit. It’s also worth noting, while we’re all for pushing the boundaries when it comes to personal style, don’t be the guy wearing a pair of suit shorts – just don’t.

oliver cheshire summer suit mens street style
Oliver Cheshire summer suit men’s street style



Finally: the shoes. No outfit of Cheshire’s is complete without strong footwear to take it to the next level. If, like him, you plan on going for an ankle grazing cut trouser – a good shoe is a necessity. Opt for suede lace-ups, polished brogues, monk strap shoes or fringed loafers to bring your outfit together under the defining tone of your footwear.

Remember, smart shoes needn’t be saved for formal occasions – they can elevate a pair of jeans a treat, striking the smart-casual gong so well people will think you coined the term yourself.

Smart Shoes

Oliver will often opt for a smart shoe choice regardless of the outfit. While this can work to elevate a casual outfit into something slightly more dressy, it’s not a surefire winner. Obviously colour, material and general style has to be considered when matching, and that’s before you’ve even looked at the dress code.

The three options below will leave you covered for almost any eventuality; classic colours such as brown and black will always be a classic, but if you want to mix things up a little bit then you can always opt for an oxblood pair to really make a statement.



When it comes to boots, suede is the perfect marriage of casual and formal working well with everything from suiting to a laid-back jeans and t-shirt ensemble.

While the desert boot is a perfect example of this, for that quintessentially British feel – it’s got to be Chelsea boots. A dark brown option, will work with almost any smart or casual outfit options making it one of the best options out there for those looking for a ‘one-suits-all’ pair.



Over the past few years; the rise of luxed-up trainers, partnered with their new-found social acceptance, has made them a crucial component of every man’s wardrobe.

If you’ve yet to get on board the trainer train (sorry), a simple white pair is your best starting point. Working perfectly with jeans, chinos, joggers and even suiting, they’re hands down the most versatile pair of shoes you can own.


Oliver Cheshire The Model

As with most his counterparts, Mr.Cheshire’s branched out from exclusively modelling and has taken to reporting for GQ and The Telegraph alongside writing for his own blog. This being said, his bread and butter comes from several large campaigns with global fashion brands such as Dolce & Gabbana and Hugo Boss.

Take a look at some of Oliver Cheshire’s most iconic fashion campaigns below.

Oliver Cheshire and Calvin Klein

After being scooped up by Calvin Klein at the young age of 17, Cheshire was quickly introduced to the main man himself, Calvin, before starring a series of shoots for the brand. He quickly rose to success following this after being plastered across NYC billboards in little more than his smalls.

oliver cheshire calvin klein
PHOTO CREDIT: Calvin Klein


Oliver Cheshire and Hugo Boss

Cheshire’s strong relationship with Hugo Boss is no secret, having modelled several campaigns for the German brand. Alongside his numerous ad campaigns, Oliver has also been the face of their body-wear line as well as participating in charity events including sailing on the Boss yacht.

oliver cheshire hugo boss


Oliver Cheshire and Pixie Lott

When it comes to couple goals, Oliver and long-term girlfriend Pixie Lott have been serving us some seriously stylish looks for a number of years now. Check out some of their best coordinated #couplegoals inducing looks from over the years.

oliver cheshire pixie lott

How to Dress like Oliver Cheshire

  • Fit is a fundamental element of Cheshire’s looks. Suits should be tailored, other pieces should be altered to fit the body.
  • Well made, classic pieces are more important than trend-led, seasonal bits.
  • Footwear can make or break an outfit – it shouldn’t take a back seat.
  • White trainers are the ultimate footwear choice for both smart and casual.
oliver cheshire navy ouvershirt striped breton t-shirt and black jeans mens street style
Oliver Cheshire wearing a navy overshirt and a breton striped T-shirt mens street style


On That Note

And there you have it. As mentioned previously, the key to emulating Oliver’s style is all in the fit. Classic, simple pieces in good quality is the key. While (unfortunately) we can’t give you any guidance on where you should be heading for a pair of cheekbones like Cheshire’s, this guide should give you a good foundation on dressing like one of the finest dressed men in the country. You’re welcome!


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Easily one of the best dressed men in Britain; Oliver Cheshire’s contemporary, stylish flair is admired by many-a-man. Check out our complete guide with tips...
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