The best things in life get better with age: wine, cast iron pans, Messrs Clooney or Beckham (take your pick). It’s a rule that’s equally true of the enduring icons of the male wardrobe.

In a world of disposable fashion and fleeting fads, it’s comforting to know that some staples are in it for the long haul.

From the buttery wrinkle of fine calf leather to the body-hugging wrap of raw denim, here are the items that will go on getting better and better as you do. Say hello to your newest old friends.

Leather Jacket

Like a human’s, cow skin warps and wears to tell the story of that which inhabits it. Good leather jackets crinkle and mould along the joints and around the seams, becoming suppler and better fitting as they are broken in.

Even better is the subtle patina and colour distortion that appears along the collar, at the elbows and around the pockets. A serious piece of hide will last you your entire adult life – and because it’ll look good in such a wide variety of situations, it’ll collect just as many stories as you do.

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Flannel Check Shirts

Trace the flannel shirt’s family tree and you trace a line through cowboys, dead presidents and every off-duty movie star worth his salt. One reason for its enduring appeal is how much it matures as we do: from a bright, slightly coarse cut of fabric to a gently faded, even haggard layer.

Flannel, with its soft, dense fibres, is particularly good at conforming to your body, while its lightly absorbent nature means the dye very gradually bleeds from it, allowing it to mellow with age.

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Raw Denim Jeans

Raw denim, not to be confused with selvedge, refers to a fabric that is unwashed at the manufacturing stage, meaning the dye clings to the cotton fibres in a deep indigo hue. This has two advantages for the jean connoisseur: it means that the cotton is more pliable and will mould better to your legs, and also that the dye will take on unique and natural characteristics.

This charm is best observed in the ‘whiskers’ that form over the period of several years: warm fade lines and natural blemishes around the thighs and behind the knees that are unique to every wearer.

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A Bronze Watch

Most men’s watches just go round and round in circles, but a bronze watch changes day-by-day. The real joy of owning a timepiece in this delicately reactive metal is the progress it makes across a lifetime: from a golden sheen to a heavy russet and finally a darkened, gunmetal brown.

The patina of the metal grows in depth, too, lending the bronze a highly distinctive look compared to its shinier, showier counterparts. More intriguing still is the natural variance in patina shades. Because the rugged metal’s colour is affected by atmospheric pressures, altitude and humidity, the places you go and the life you lead will be reflected in its darkening tones.

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Canvas Sneakers

Nowadays, everyone seems to have bought into the great lie that our casual footwear needs to look box-fresh every single day. While this might be valid for some luxury sneakers, pristine white uppers can feel a little clinical and calculated.

Much more charming is a battered and bruised pair of Converse Chuck Taylors or a lightly frayed pair of low-top Vans. With cotton-based shoes, the dye fades to give an understated, warmer feel, while the gradual melding of the rubber and canvas will hug your feet like especially friendly memory foam.

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Leather Wallet

Accessories may be small but they’re not insignificant, so it makes sense to invest for the long run. Case in point: a good leather wallet in which to keep your hard-earned until retirement and beyond.

Owing to its pliable design and supple construction, a billfold softens with age, conforming to both its contents (which we’re sure will balloon over time) and its owner’s body shape (which we hope doesn’t).

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Trucker Jacket

The timeless layering option doesn’t just tide you over from season to season – it actually gets better and better with every wear. Like its leather counterpart, the hardy denim jacket takes on characteristics that are unique to its owner, based on wash patterns, body shape, and what you do while wearing it.

What’s more, the discolouration and blemishes that the trucker develops only add to its appeal, ensuring that the garment stays true to its rugged, workman roots.

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Well-Made Leather Shoes

The foundation on which all good looks are built, once broken in, a decent pair of leather Oxford or Derby shoes will mould to the contours of your feet, growing more comfortable with each wear.

But despite what mothers will tell you, it’s not just what’s on the inside that counts. On the exterior, the grain begins to express itself more fully, gaining a pleasing depth over the years.

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Velvet Dinner Jacket

The rakish black tie fixture lends a timeless sophistication to a formal look. That’s partly thanks to the sheer decadence of velvet, but it’s also due to the way that the material develops with the passing of time.

Because the fibres in velvet stand up in a tufted pile, each wear gently crushes and moulds the rich fabric, giving the blazer a deep and distinctive appearance as well as a softer handfeel.

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Baseball Caps

Like so many other unfussy menswear pieces, baseball caps have the ability to become a second skin given enough time and patience. If you want a cap that conforms to your cranium, you might have to wait a few years, but the results are worth tipping the brim to.

Both wool and cotton versions shrink with heat and moisture to take shape over time, while seams pucker slightly and the brim achieves its own unique curve that frames your face perfectly.

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Goodyear-Welted Boots

Boots are made to be put through their paces: a pair of pristine kickers is a sign of a life as yet unlived. But of course, you still want a pair that can be brought back to health when they do finally give in.

Those with goodyear-welted sole, a method favoured by most traditional British brands, last much longer because the process involves a tighter bond between the upper and the sole. They also use a lockstitch technique, which ensures even if one part of the welt becomes loose, the rest of the chain remains intact.


Leather Holdall

Father time isn’t always kind to skin: fine lines, dark circles, gravity. Unless, of course, that skin takes the form of a classic leather holdall, which matures and mellows over time.

Take a weekend bag around the world and it’ll pick up a souvenir at every stop: the soft fade from a sun-bleached landing strip; the supple wrinkles from a dusty desert road; the dark patina from an ice-blown helipad.

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