At their best, men’s clothes transcend the age of the wearer. That’s why we continue to admire shots of menswear icons of yesteryear – guys like Mr Pablo Picasso or Mr Gianni Agnelli, who were at least as stylish in their later years as they were in their youth. As we mature, many of us become less concerned about the image we convey to the people around us – and this mellowness is best deployed as a nonchalance about how you put outfits together and which elements you mix.

The mark of a truly beautiful thing is that it will be more appealing with age than it was when it was new – just think of a well-used leather wallet, a vintage car or even a much-loved watch. The best clothes for grown-ups also fall into this category and become part of their owner’s biography, bearing the marks of a life well-lived and gaining character and memory as they age graciously. These are clothes that will be as relevant in a decade as they are today and will look better for being regularly worn: tweed jackets mould to the shape of their owner with more frequent wear, selvedge denim fades beautifully, and workwear nicely softens up. These are clothes for the long haul and clothes that will accumulate memories as they literally become part of the fabric of your life. As such, they speak eloquently to guys whose sartorial range is beyond the first horizon. Read on to find out the items that any man, whatever his age, should have in his wardrobe.

Royal-blue workwear jackets, the design of which is heavily indebted to the classic French working man’s jacket, are admirably simple and elegant. The blue flatters almost any skin tone, the simple form lends itself to a loose, comfortable shape, and the coat works as well with jeans as it does with chinos or cords. Dress it up with a collared shirt for a gentlemanly, bohemian look, or play with the Frenchness (as above) with a striped Breton top. What’s so remarkable about these jackets is that they simultaneously speak of beatnik creativity (it’s impossible to look at these jackets without thinking of the late, lamented New York photographer Mr Bill Cunningham) and salt-of-the-earth manual labour. In real life, these are often two different worlds, but the magic of fashion can unite them.

Big coats are big news this season, but for some men they never went away. Many of the world’s snappiest dressers have long known that soft, country-inspired overcoats strip back the heavy formality of structured versions in dark colours. Between the light colour, the rustic fabric (in this case a hairy Donegal cloth with a herringbone pattern) and the raglan sleeves this coat has a comfortable look about it. A coat like this isn’t designed to fit the body like a glove, but to drape softly around it, and it will look good worn with a suit or worn with a pair of cords. It’s a coat that you could wear over a chunky rollneck sweater to walk the dog, or over a tuxedo to a grand party. It’s also practical in that you can do up all the buttons, flip up the collar and keep out the worst weather that nature can throw at a man.

The short denim jacket, which is most commonly known as the trucker, was born when Levi’s introduced the Type I jacket in the early 20th century. Originally conceived of as an item of workwear, the jacket’s image may have altered over the years but its relevance has rarely wavered. The simple, flattering form is well established (although aficionados will have strong feelings about whether they favour jackets modelled after Levi’s Type I, Type II or Type III jackets) and the slim cut means that they work as lightweight coats in warm weather and as layering in cooler weather, as shown here. The biggest decision is whether to take the purists’ approach and go for a stiff, unwashed indigo fabric or a pre-faded jacket. Given that this is a piece with the potential to last for years, there’s a strong logic to starting with an unwashed jacket and enjoying the way it softens and fades over the years.

There’s a heavy irony to the fact that by owning lots of pairs of jeans, denim lovers wear each pair less frequently, and thus slow down the all-important process of fading. The chap in this shot appears to have just started a relationship with a new pair of jeans, which accounts for their very uniform shade of blue, and is no doubt looking forward to a day when they are well-faded. We note that this pair is relatively loose-fitting – although they’re still tidily turned up rather than puddling on top of his white sneakers – and that’s not only more in line with the increasing appetite for relaxed fits, it’s also more in line with the classic shape of jeans. When you’re buying them for the long-haul, it’s important to choose a shape with enduring appeal. Despite being in fashion ever since Mr Marlon Brando pulled on a pair of Levi’s for his role in the 1953 movie The Wild One, jeans are more relevant now than they have ever been. Other than a courtroom or a church, it’s genuinely hard to think of a place where this outfit of clean white sneakers, tidy blue jeans and a wool overcoat would be inappropriate in 2018.

There is no garment as timeless as the tailored jacket. The tweed jacket was widely adopted by college undergraduates in the 1930s because it simultaneously conveys a respectful level of formality, is flattering, comfortable and has enough rustic charm to suggest the wearer has a life beyond the metropolis. On a practical level, tweed jackets are versatile and warm, and are designed to be worn with a variety of colours and styles of trousers, from smart grey flannels (as in this shot) to chinos and jeans. With a classic fit, a tweed jacket should look as good in a decade as it does now, and they work as well on men in their twilight years as they do on university students – if only students wore such garments. It’s remarkable how varied an impression a tweed jacket can make, from being ultra-conservative to appearing decidedly raffish, and all points in between. We’ll be wearing them this autumn, and every autumn thereafter, with soft-collared button-down shirts, knitted ties, cotton trousers and suede shoes.

When one thinks of those impossibly well-dressed Italian men photographed in street-style blogs, they tend to have one thing in common (beyond their love of tailoring), regardless of their age. And that is their affection for soft-shouldered jackets. It’s worth pointing out that unstructured and soft-shouldered are relative terms, and that in reality few jackets are entirely unstructured. That said, what is clear is that the softer the shoulders, the more comfortable and light a jacket will feel and the more relaxed an image it will convey. If the wearer feels comfortable, he’ll seem relaxed. The double-breasted blazer in this shot is very soft and wrinkled – a divisive quality that will drive some men mad and appeal deeply to others (including me). What’s more easily agreed upon is the fact that these jackets are particularly useful in warm weather because the lack of structure makes them so lightweight.

The men featured in this story are not associated with and do not endorse MR PORTER or the products shown