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Middle Age Style: Fashion Advice For Men In Their 40s

Mid-life style can be a veritable minefield so read our guide on how to successfully navigate your look through your 40s.

Words by: Ryan Thompson

Let it be said that fashion is a young man’s game, but style should never desert you. That’s all very well in writing, but when one enters one’s 40s, there are a multitude of variables that seem wholly dedicated to thwarting any sense of good style you may have once possessed.

It’s typically a deadly combination of lifestyle factors that is the rag in the once finely tuned machine – a senior work role, children, dogs, a generous consumption of wine, infrequent gym visits, stress – you name it, it tends to say hello in your 40s.

This writer is in his third year of his fifth decade on this planet, so I’m not about to spout mere platitudes at you. I’ve been through the style trenches and have seen many a friend and colleague wither in the pit of middle-aged complacency.

So if you’re reading this and you’re in your 40s, just know that looking good is not a nostalgic town in your rear view mirror, but rather a destination that is very much commutable. And I’ll show you the quickest way there.

It starts with your body

Luxury home gym setup

There’s no other way to say it. If you’re out of shape, clothes just aren’t going to look that great on you. We’re not talking about a 25-year-old gym rat body, but rather a physique that is healthy and strong, and most importantly, that you’re proud of.

Our sedentary lives and a natural decline in testosterone production make it very difficult to maintain a healthy weight, even if we are going to the gym regularly. The best way to achieve weight loss is through a manageable calorie deficit. Forget ‘dieting’ per se, and focus more on a relatively high-protein approach, tracking your calorie ins and outs.

Aim for a reasonable deficit that doesn’t make you want to eat the family dog. Make it so that it easily becomes habitual, too (eating the same weekly meal plan over and over might be boring but it seriously works), and you’ll reach your target weight without too much stress.

The quick-fix haircut

A man in his 40s getting his haircut at a barbers

If there’s one thing guys in their 40s neglect more than anything, it’s their hairstyle. Sure, you’re probably out of the mating pool by now, or maybe you’re trying to get back in it? Either way, a clean regular chop will do instant wonders for your overall look.

Naturally, you don’t want to get anything wild or ‘trendy’, but rather a classic haircut that best suits your face shape and hair type. This is where it pays to visit a senior stylist at a great salon or a modern barber.

There is no ’40s haircut’ – there is only your haircut. If your hair is starting to thin, don’t try to disguise the area with your remaining hair. You’re fooling nobody. Unless you’ve been living under a rock, you won’t have failed to notice that you are living in the heyday of hair replacement therapy. No snake oil ointments, but real scientifically proven methods to reboot your thatch. From caffeine shampoos and Propecia to full-on hair transplants, your barnet has the means to be resurrected.

A man in his 40s wearing a tailored suit with a shirt and tie


The old adage ‘dress your age’ is old because it’s true. Trying to appear younger by impersonating a younger generation is an unmitigated disaster, and only serves to highlight your true age. So what does dressing your age when you’re in your 40s actually mean?

Well, what it doesn’t mean is jumping on seasonal fashion trends, which become tired and outdated quicker than you can say ‘Balenciaga speed socks’. Instead, opt for timeless menswear silhouettes and shoe styles that you can elevate with the occasional bit of fashion indulgence.

High-end tailoring, for example, never gets old, only the silhouette changes according to menswear’s whims, so it’s always a good idea to invest in smart suits and separates. If you want to be more modern, then opt for more relaxed fits, or stick to a minimalist monochrome palette.

But don’t be a wallflower

Man wearing blue jeans, green shirt, suede blazer and sunglasses


On the flip side of avoiding fleeting trends is the reluctance to be creative or push your boundaries, which can risk the result of a stultifying wardrobe of overly safe silhouettes, colours and patterns. Don’t fall into that trap.

Silhouettes such as bomber jackets and blousons, or a bold statement coat, can be just the injection of youthfulness your wardrobe needs without having to try too hard.

Add some bold block-colour fine-gauge knits, or opt for great-fitting selvedge denim jeans, or some beautiful checks to keep your fits looking fresh but without having to rip your comfort zone a new one, so to speak.

Dress for your body type

Men's black pleated trousers, camel v-neck sweater, camerl overcoat and suede brogues outfit

Brunello Cucinelli

We’ll get into made-to-measure options shortly, but otherwise a good rule of thumb is to dress to complement your type. We emphasise this in an article about style in your 40s because the pressures of life often mean that we don’t quite have the physiques that we would like. So being smart about the pieces we wear, or the palette we adopt, can help smooth out the edges.

For example, if you’re top heavy, then opting for cropped blousons such as denim jackets (or any other style that finishes high on the waist) is only going to emphasise your midriff. A better option would be to wear longer overcoats and jackets to create a more svelte silhouette.

Conversely, if you are short, you want to use cropped jackets to your advantage since they will make your legs appear longer, especially if you wear tapered trousers and boots.

If you’re skinny, structured tailoring will help to emphasise your shoulders. Larger guys should also avoid striped tops, whereas checks are a more disruptive pattern that will disguise your dimensions.

Invest in high quality essentials

A selection of high quality men's wardrobe essentials for men over 40


When you get to your 40s, you probably shouldn’t be stepping out in looks that turn heads everywhere you go. Instead, the emphasis should be on refinement and quality, especially when it comes to wardrobe essentials such as T-shirts, crew necks, underwear, and so on.

The difference between a multipack white cotton tee and a heavyweight Japanese 100% organic cotton T-shirt is magnitudes, for example. So, where possible, look for the best natural fibre options available and invest. They’ll look better, feel better and last much longer than the cheap options.

Speaking of longevity, make sure you have a decent rotation of basics too. If you’re washing the same few pieces week in, week out, you’re going to quickly degrade them.

Wear the right colours for your skin tone

White man and black man in their 40s dressed in complementary colours to their complexion

Thom Sweeney

This one applies to everyone regardless of your age, but wearing colours that complement your specific skin tone is something many guys never consider. Clashing colours in your look is one thing, but clashing your clothes with your face is not recommended.

To ascertain your skin tone, simply take a piece of white paper and hold it next to your face. If your skin looks yellowish, greenish or light brown, then your skin tone is warm, so colours such as red, orange, pink, olive green and cream will suit you well.

If your skin looks pink, rosy, or blue, then you have a cool skin tone (or are a Smurf), in which case greys, blues and pastels are perfect.

If your skin looks grey then you’ve probably got a neutral skin tone, in which case the colour wheel is your oyster.

Frames that fit your face shape

40s man wearing luxury spectacles

Kirk Originals

This is a quick fix to instantly polish your aesthetic if you’re a glasses wearer. A lot of visually challenged guys in their 40s end up going for cheap frames and maybe even buying a couple of pairs of them in case the dog eats one or the toddler gets handy with them.

We can understand the practical approach, but it does nothing for your look. Take it from someone who has worn glasses for the last 25 years – a great pair of specs are nothing short of transformative. Why would you not emphasise and invest in the one place on your body that everyone looks at when talking to you?

Invest in a quality spectacles brand and if you’re unsure what frames suit you best, visit your local eyewear boutique and ask for some impartial advice. You might even come round to the idea of wearing different frames for different looks, but one step at a time.

Build a capsule wardrobe

A minimalist men's wardrobe


As style advice goes, this applies to all men – but especially guys in their 40s who are short on time thanks to the persistent juggle of responsibilities. Rather than get overwhelmed by trying to work out all of the permutations of your entire wardrobe, break it down into capsules of, say, three or four interchangeable looks.

You could do it tonally for example, segmenting it into a navy capsule, or a tan and neutrals capsule, or an all-black capsule. Then when you next go shopping and find something you like, you’ll have a much clearer idea about how you’ll be able to incorporate it into that relevant capsule.

Have a ‘uniform’ to fall back on

Man in his 40s wearing a black polo shirt and black jeans

Buck Mason

In a similar vein to building capsules into your wardrobe, having a uniform style that defines your aesthetic is another great way to take the stress out of looking good each and every day. It can be as specific or as broad as you like, so long as it is visually definable.

For example, something that a lot of fashion industry people do is just wear black, or at least majority black. It’s chic, sophisticated, a doddle to style and you can add the occasional flash of colour to keep things interesting.

Maybe you’re more of a greys and neutrals kind of guy? Your uniform could be more generic, such as you only wear workwear silhouettes (and in that you can get more specific, like making the chore jacket in five different colours your thing), or alternatively it could be something specific, such as selvedge denim jeans and flannel shirts.

Whatever it is, make it somehow unique and obvious to you.

Consider made to measure

Thom Sweeney made-to-measure studio

Thom Sweeney

If you don’t already have the Adonis body by the time you hit 40 then let me bring you down to earth gently: it’s unlikely you ever will. Your natural T-levels only get worse from here, so unless you’re thinking about going the TRT route, chiselling your body into something resembling Hollywood hero is going to be a task beyond you, especially when you factor in your other responsibilities (and that wine collection you’ve been accruing).

But with age comes more disposable income, which leads you neatly to the opportunities offered by the made-to-measure and bespoke world. It’s there that a good tailor can disguise your contours and simply make you look better than your naked photo would attest to.

Bespoke is of course hugely expensive, but made-to-measure (M2M) tailoring is a fantastic alternative that has significantly improved in recent years. Yes, it requires you to have something near an ‘average’ body shape, but if that sounds like you, it could be well worth considering.

A lot of Savile Row houses offer M2M options that are good value and give you a taste of the bespoke process.

Adapt your grooming routine for mature skin

Man applying an anti-ageing grooming product

As I know only too well, when you’re in your 40s, you tend to wear a hangover for days, so your skin needs all the love it can get. Your collagen levels drop, leading to a fall in the elasticity of your skin, which means a tired, dull-looking complexion. There’s no secret age-reversing cream but there are certainly things you can do to minimise the haggard vibes.

Scrubbing with a gentle exfoliator a few times a week and applying a moisturiser daily is the base case, but from there you can kick on with the unsung hero of male grooming – the under-eye cream. Dermalogica’s Awaken Peptide De-Puffing Eye Gel works wonders on eyes that haven’t seen eight solid hours for a while. Look for creams with caffeine, niacinamide or peptides to give you that lift.