Let these smart, seasoned men teach you a thing or two about how to dress.

It’s no coincidence that many of the world’s best-dressed men aren’t in the first flush of youth – just think of Messrs Ralph Lauren, Bryan Ferry, Luca di Montezemolo and Terence Stamp. They might have gained a wrinkle or two, and even put on a pound or two, but, as they say in China, “old ginger is spicier”. But where, in style terms, does that spice come from? Is it the fact that older men are more likely to wear well-made tailored clothes? Is it the confident way they use colour? Or is it just that, beyond a certain point, a man’s attention switches from making his body beautiful to making his wardrobe beautiful?

Perhaps it’s none of these things, and instead it’s down to personality and the quiet sense of self that builds as the years accumulate. Because the men in these images have something special, something that goes beyond the colour combinations they put together, beyond the cut of their jackets or the angle of their fedoras. In some cases, it’s simply a sense of steely confidence; in others, a twinkle in the eyes. Fine clothes are necessary, but not sufficient. If you want to dress like a master rather than a mannequin, it’s vital to be at ease with yourself, and to allow your inner spirit to shine through. Although a capacious wardrobe full of beautifully tailored clothes certainly helps.

There’s a lot going on in the image above, from the 1930s-style sunglasses to the canvas waistcoat, via the cigar, the checked jacket and the tie. Yet it works because, although the white shirt, sand-coloured waistcoat and hound’s-tooth jacket are read as separate elements, they don’t strongly contrast with each other; that job is left to the dark navy silk tie. It’s hard to overstate the versatility of such a piece. Meanwhile, the jacket’s soft shoulders put both the wearer and the viewer at their ease.

Pearl of wisdom: neglecting your grooming regime can occasionally pay dividends.

The double-breasted camel overcoat is one of the sartorial trophies that every clotheshorse wants to have in his wardrobe. A surprisingly versatile garment, it works over relatively casual clothes (think grey flannel trousers and a cream rollneck) as well as with formal outfits such as a dinner jacket. In this case, the generously proportioned coat sits harmoniously over a pale blue shirt, a grey jacket, a navy and brown tie and a bottle-green scarf. As ever, the details are vital, from the horn buttons to the elegant roll of the lapel and the turn-back cuffs. But none of these elements is quite as effective as the wearer’s palpable self-belief – something we unfortunately don’t sell on MR PORTER (yet).

Pearl of wisdom: when buying tailored clothes, there’s much to be said for investing in well-executed classics.

These grandees of the Italian fashion scene (Mr Beppe Modenese, right, is honorary chairman of the Italian Chamber of Fashion, while Mr Mario Boselli is its ex-president) were captured conferring after last summer’s Missoni fashion show in Milan. Both are in sober navy blazers, with the man on the left wearing a single-breasted number with a very pale blue shirt and a very bold tie. Mr Modenese has gone for a double-breasted jacket, which he’s wearing with a superbly coordinated striped shirt and yellow tie (you’ve noticed the shirt’s yellow stripes, right?). The details, as ever, make all the difference, from the brown band on Mr Modenese’s Panama hat to the dimple on his tie and his blazer’s substantial cloth.  

Pearl of wisdom: on a sunny day, nothing pops like a yellow tie.

Most men neglect green when it comes to their wardrobes, but even style pundits (perhaps influenced by Kermit the Frog’s famous song “It’s Not Easy Bein’ Green”) rarely advise men to wear two eye-catching shades of green at the same time. This resplendently white-haired chap is, however, untroubled by such timid sentiments and, wilfully disregarding Kermit’s advice, has gone all-out with his unbuttoned double-breasted jacket. Just in case the jacket’s shade of green lacks punch (and it doesn’t), he’s taken the precaution of adding a hi-vis pocket square and wearing emerald green trousers. It’s not a look to be attempted by the faint-hearted, but my goodness this brave soul makes it work.

Pearl of wisdom: if a man can walk with a straight back, and look entirely unaware of his outrageous outfit, then he can get away with almost anything.

Articles about senior style usually focus on the fact that the older generation seems to have the ability to faultlessly deploy formal codes of dress. So it’s refreshing to come across this first-class example of smart-casual. A felt hat may be a traditional accessory, but this purple example gives a quite different impression – something much more creative. The overcoat is actually quite casual, thanks to its raglan sleeves and the fact that it buttons up to the neck, and the jeans are quietly subversive in this context.

Pearl of wisdom: don’t be afraid to mix casual clothes with classic elements of menswear.

Your eyes are not deceiving you – Mr Modenese does, in fact, appear twice in this feature, which is rather unsurprising for someone once described as “the prime minister of fashion” by fashion bible WWD. In the above shot, he’s demonstrating the enduring power of a beautifully made double-breasted blazer, particularly when the shoulders are soft but still have a little roping (ie, the sleeve head stands slightly above the shoulder line). He’s also demonstrating the less well-known harmony that can be created when a navy blazer is worn with a green tie, a combination that seems to work particularly well when the checked shirt is read as a wholly separate element from either the jacket or the tie.

Pearl of wisdom: everything needn’t match all the time for you to look good.

Few outfits broadcast the identity of their wearer more clearly than this – it positively shouts “stylish old Italian man”. The most ageing element here is the width of the trousers, based as it is on the golden age of style, rather than contemporary preferences, but they’re beautifully cut and the length is well judged. The shoes are another classic element, and are as right today as they would have been half a century ago. Green loden coats such as this (which are Austrian in origin) are unfairly neglected, but work well to keep out the cold and strike a less formal note than more structured overcoats. The red scarf is a cosy addition and adds a visual pop.

Pearl of wisdom: wearing country-inspired tailored clothes is a fresh alternative to more predictable city suits and jackets.

Grooming becomes increasingly important later in life – once a man’s hair is white it normally benefits from an intensified maintenance regime, particularly if said hair also covers his face. It’s safe to assume that this gentleman takes an active interest in every aspect of his appearance, from his coiffured hair to his fox-coloured suede shoes. The slim jacket accentuates his trim figure, while the stone-coloured cotton trousers are correctly finished with chunky cuffs at the appropriate length. The scarf adds a casual note (the overall impression would be very different if we could instead see a tie), but, quite frankly, it’s the old-fashioned bicycle that’s the key accessory here.

Pearl of wisdom: in the summer months, clothes in shades of olive and stone combine particularly well.

This checked sports jacket brings to mind an old anecdote about a Savile Row tailor who, when asked by his customer if he thought a particular tweed was loud, replied, “Loud, sir? I wouldn’t say it was loud, but it does mutter a bit.” There’s nothing wrong with clothes that mutter a bit, when they’re worn with aplomb, and in this case the navy blue overcoat and the navy blue tie act to subdue the slightly outlandish sports jacket. The sky-blue striped shirt, eye-catching Ferrari-red scarf and lavender-coloured pocket square, however, serve to crank up the volume. The net result is a balanced outfit that still draws our attention.

Pearl of wisdom: a sober tie can pull together an outfit that could otherwise look rather jazzy.

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