Oliver Cheshire is a professionally stylish man. It’s easy to assume that some glass-cutting cheekbones and piercing glare are all it takes, but while Cheshire has taken good advantage of what his mamma gave him, his countless campaigns and magazine covers aren’t that easily won.
Genetic lottery aside, a modelling career takes work – in the gym, in the studio, on social media – especially when you’re as au fait with Dolce & Gabbana’s catwalk as you are with being the face of high street stalwart Marks & Spencer. Cheshire is also a menswear maven, as composed in a dinner jacket as he is in some risk-taking streetwear. He looks good because he knows how to – which is why we cornered him recently to pick both his brains and his threads.
Say you’ve lost your entire wardrobe in a blaze. What are the five go-to pieces you rebuild with?
Ah, that sounds like a personal nightmare. If I did have to start over, it’d be with a dark navy pair of jeans: they go with most things. Then a white T-shirt, all the way, plus a shearling jacket for when it comes in cold. M&S currently has quite a boxy, wearable black-on-black iteration that’s relatively clean: no big toggle buttons, just a simple zip-up front.
Then, I’d go for a quality plain shirt for layering and some plain, minimalist white kicks – they’ll ground almost every look imaginable.
When buying new pieces, try to think of colour palettes: what will go with what, and how some tones – your neutrals, your whites and your navies – get more wear than others.
If you’re looking to invest in one piece, what should take precedence in the purchase – the label, the style, the fit or something else?
The fit, 100 per cent. The average guy only pushes boundaries so far with fashion – and that’s not necessarily a bad thing – so fit is one of the few things that can make you feel amazing, regardless of your height, your weight or your looks.
A perfectly fitting suit, whether it’s £100 or £1,000, can make all the difference to your finished look, and the same rule applies to everything else in your wardrobe. I always apportion a part of my budget specifically for alteration, and my local guy – just a dry cleaning service – knows what I want. These people get to know you after a while, and offer a relatively inexpensive service for something that can make any clothing look designer.
Men are taking more care with grooming. What’s your foolproof morning routine for the day ahead?
I use a Jan Marini face cleanser daily – it’s really refreshing, and good for oily skin. Because of that, I moisturise with a Lab Series matte finish: men don’t use make-up or powder, so a moisturiser is one of the few tools that can prevent shiny-looking skin.
When showering, I also think it’s important to go freezing cold right at the end. It’s a brave move, for sure, and it’s hard, but it closes all those pores, which is important when you live somewhere as smoggy as London.
It’s probably worth taking a look at diet, too. I stopped drinking milk because a certain hormone can trigger bad skin and malaise, so maybe consider switching out big dairy products for an alternative if you’re suffering a breakout.
We live in the age of Instagram. Whether you’re chasing the likes, or simply looking for a killer profile picture, how can a man look better on photos?
Don’t take yourself too seriously. If you’re out with mates, don’t be blue steeling in the background – just try to look happy.
Putting your chin down slightly can make your face appear slimmer, but don’t overdo it – it’s just a tilt. People have a natural habit to put their chin upwards, but it rarely looks that flattering.
Second, lift your eyebrows. It makes you look happier, but again, keep it subtle as go too high and you’ll just look surprised.
Then for your body, shoulders straight to the camera and hips a fraction to the side. This slims down the waist but builds bulk on your top half for photographs. That’s the easiest trick for the camera, and it emphasises a body shape most men want.
What can the everyman take from your pre-shoot, quick-fix detox mode?
As I’ve got older, self-maintenance is getting more important before a big shoot. So, I make sure to get good sleep, drink water (not alcohol) and tonnes of cardio. Models aren’t big and muscly; everything has to be in proportion and clothes are getting smaller and smaller and smaller – even for us guys.
What does your model workout look like?
I train 40 to 45 minutes a day, but it’s a case of listening to your body. If you’re aching and feeling knackered, have a rest: otherwise you could injure yourself, and it won’t be a good workout.
Try to concentrate for 20 to 25 minutes on cardio, get the blood pumping because that’s how you’ll lose weight. Then, focus on your whole body as opposed to say, leg day, or chest day. I move from top to bottom in rotation for something I call a ‘jailhouse workout’ – push-ups, chin-ups and sit-ups. It’s about using your bodyweight and high-intensity moves, and keeping up the heart rate.
What’s your tip for looking stylish when you just can’t be arsed?
Find your go-to outfit. Know what looks good, buy several, and resort to that on the days when you couldn’t care less. For me, it’s a black tee, washed out jeans and some white trainers – Air Max or whatever.
That’s not to say it’ll suit everyone, but opt for staples and stick to casual. I only really dress up for events, so most days are filled with my old favourites.