How To Dress Well In Your 40s: A Modern Man’s Guide

They’re meant to be the toughest years of your life. There’s family to look after – both your own and your parents; your body starts to really remind you that, no matter how hard you try to imagine differently, your physical condition has started on the downslide; and for many men it’s a period of disturbing reflection and awareness – that your youthful expectations of how life would be haven’t exactly panned out. Worse of all, you’re not allowed to wear three-quarter length trousers anymore.

Okay, so you were never allowed to wear three-quarter length trousers. Nor flip-flops, nor sleeveless T-shirts, nor too much jewellery, nor football jerseys (unless you’re actually playing football) – not if you have any self-respect at least. Yet there is this notion that once you reach a mid-point in life – mid-point if you’re lucky, at least – certain sartorial options are closed to you. Anything that smacks of youth is suddenly disallowed by some anonymous, invisible, unaccountable authority known as public opinion, as if the public is really paying any attention to what you’re wearing.

Dress codes aren’t as rigid as they were back in the 1960s and 1970s.

That may have been true of our father’s, and certainly our grandfather’s, generation: dress codes were more rigorously age-specific. But then, for our grandfathers at least, the relationship between age and attire was rigid effectively as soon as they entered the workplace; from that point on, one dressed with sobriety and conservatism, and did so more or less unto death. There was no “business casual” back then.

But that situation has flipped: rather than the dress of adulthood being applied as soon as possible, now the dress of youth has been extended well into our older years. Men now entering or in their 40s are the first generation to have grown up with the idea of men’s fashion being an established norm rather than a wacky exception. And, more recently, also with the idea of style being a product of mixing and matching clothing of varied references, periods and functions – a bit of sportswear here, a bit of tailoring there – without any of it suggesting too much.

The New Relationship Between Age & Clothing

That’s all changed our perception of the relationship between age and clothing. Seeing even a 70-year-old in, say, a hoodie, doesn’t invite ridicule; the complete opposite, in fact – if he’s wearing it well, he might look pretty damn cool. Many individual items of clothing have had to shake off the shackles of being associated with a youthful time of life: jeans, trainers, even T-shirts. But we no longer associate these with youth any more than we automatically associate ties, shirts or suits with being closer to the grave.

Idris Elba is one of a number of high-profile 40-year-olds proving age is just a number when it comes to style

So, thankfully, the strictures on dress as you fight through your middle years are not as stringent today as they were just a couple of decades back. If a man does feel awkward wearing the kind of clothing he might once have worn, that says more about his state of self-consciousness than it does about what is expected by other people.

An interest in self-expression, in style, in fashion – it doesn’t stop because you’ve had a certain birthday. It’s about your attitude – one benefit of middle-age is a confidence to be your own man; and to not much care what other people think. You like it. You wear it. These, after all, are times of “middle youth”. Besides, why should a curiosity about the latest clothing trends be confined to youth anymore than an interest in, say, the latest in music or art? The younger generation own none of these anymore.

David Beckham, Idris Elba, Ryan Reynolds (featured image), Kanye West, Jon Hamm, Mahershala Ali – there’s just a selection of 40-somethings widely considered to be some of the best-dressed men on the planet (and setting trends in their own right); other regularly touted icons such as David Gandy, Ryan Gosling and Virgil Abloh are quickly approaching the big four-oh; while the likes of Jeff Goldblum and Bill Nighy are proving that good style can last well beyond retirement age.

Are There Still Things You Shouldn’t Wear?

Even pieces as polarising as cargo pants aren’t off limits for 40-year-olds if you know how to wear them right

Does this welcome new era mean there are types of clothing that the middle-aged still shouldn’t wear? Perhaps, but only when it comes to the finer details. Read many a guide and they will, for example, pick on cargo/combat pants as an absolute no-no for men over 40. But why? There’s no logic to it. Yes, arse-squeezing, crop-legged combat pants might not look so great. They probably don’t look great on anyone much over 18. But an original 1960s pair in sateen olive drab? With a sweater and some white old-school pumps? Sounds good to me.

Sure, context is key: the workplace, and any status you might have achieved in it by your 40s, no doubt imposes certain limitations. But that’s just at work, and very much dependent on what your work is. Fitness is a factor, too – if your 40s have seen you let it all go, that’s going to limit what you might look good in. Signs of ageing (a paunch in particular) are especially unforgiving when contrasted with clothing that might still be considered by some to be youthful.

David Beckham understands the importance of maintaining a quality grooming regime as you get older

Grooming matters just as much: get a regular haircut; wash, brush and comb; moisturise; keep the beard in check (but not topiaried); use a bit of concealer, if you like. It won’t hurt you. Being trim and tidy goes a long way to giving licence to wear what you want. To this end, faking being trim also matters – which is to say wear clothes that fit well, investing in a good tailor/alterations service if required.

These considerations aside, arguably the brash and the extreme in clothing are both worth avoiding: trainers are fine, but perhaps not trainers that look as though they’re from the future; T-shirts are okay, but ones with novelty graphics less so; by all means wear your brands, if that’s what you’re into, but keep them very light on the logos; avoid fashion’s moments of playful proportions, be that voluminous or skin-tight. Few things look worse than a portly bloke in spray-on jeans.

Use Common Sense

Dressing in your 40s doesn’t have to be boring. Simply invest in quality and keep it simple.

So what does all this amount to? That’s it’s less about not wearing certain categories of clothing as the choices you make within those categories. The golden rule might well be wear what you want, but keep it plain, simple and as high quality as you can afford – because it’s being able to afford the best quality versions that arguably you express your growing wisdom and worldly sophistication.

Think less is more. Keep shapes clean and colours kind to your skin tone. Dress classically – without thinking that classically means tweed suits and brogues. Dress up – in the sense of avoiding slobbiness – without thinking that this means looking traditionally smart. It’s not the same thing.

And did we mention that you should never wear three-quarter length trousers? Like, never. Never-ever-ever.

Josh Sims

Josh Sims is a London-based men's style writer contributing to the likes of The Times, Wallpaper and CNN. He is the author of several books on menswear, including the wildly popular Icons of Men’s Style. He is also the former executive editor of Arena HOMME+ magazine.