20 Investment Pieces Your Autumn/Winter Wardrobe Needs

If you start to feel your eyes beginning to roll at the mere mention of ‘investment piece’, we get it. In an era of high living costs and persistently high inflation, the phrase has been weaponised to make anything ludicrously expensive sound somehow worth it.

And let’s be totally honest, unless you’re buying Birkin bags or a jacket worn by Elvis, 99.9% of clothing purchases are not ‘investments’ in the literal sense. But while clothing may not accrue monetary value, there is a lot to be said for spending more to get better quality, greater longevity and, ultimately, more enjoyment.

The ‘investment’ can be emotional too. It alters the way you feel about a garment, how much you cherish it and, crucially, how well you look after it. Then there’s the cost-per-wear argument: a £1,200 coat worn 300 times over five winters costs £4 an outing; a £150 one that surrenders by February could end up costing more per wear.

So what follows is our guide to buying pieces you’ll love now and for years to come, because they’ve been crafted to last and, in many cases, will only get better with age.

The Best Men’s Overcoat To Invest In

Start with the cloth. A proper overcoat wants a wool or wool-cashmere weave heavy enough to drape naturally, with a hem that falls at or just below the knee. Fashion cuts go off faster than spilt milk, so stick to time-tested silhouettes.

Look for horn buttons, a full lining that can be replaced as the years go by and a shoulder with some backbone. Muted tones will give you the most versatility, but it’s often the texture of the garment that makes people look twice.

Dunhill Checked Wool, Silk And Cashmere-Blend Coat

Dunhill started out in 1893 kitting out pioneering motorists and has treated outerwear as serious engineering ever since. In this beautiful coat, the wool supplies the backbone, the cashmere the softness and the silk a faint sheen that moves the check from country to city.

If you like your wardrobe monochrome, this is the icing on the cake.

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Oliver Spencer Morgan Double-Breasted Wool Coat

Made in England from a heavyweight pure wool that treats a north-easterly as a minor inconvenience, Oliver Spencer’s Morgan coat is double-breasted, belted and cut in a deep green textural wool that says old money rather than army surplus.

It carries the weight and gravitas of a coat at twice the price.

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The Best Men’s Down Coat Worth Buying

Here, the numbers on the label matter more than the name on it. Fill ratio refers to soft down versus stiffer feather. A 75/25 mix is respectable, while 90/10 is firmly in luxury territory. Fill power measures loft: above 600 and you’re warm; above 700 and you’re smug.

Technical nylon outer layers are the default thanks to their hardwearing characteristics and modernist aesthetic, but you can also find cracking options in more traditional fabrics such as wool and cotton corduroy.

Stone Island Crinkle Reps Down Jacket

Crinkle Reps is Stone Island treating fabric like a lab experiment. The tightly woven nylon is dyed after the jacket is made, so the colour settles unevenly into the crinkle and no two are quite alike.

It’s also treated with an internal resin coating to make it wind-resistant and mildly water-resistant. The badge on the sleeve is one of the few logos in menswear that signals genuine engineering rather than mere branding.

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Polo Ralph Lauren Quilted Cotton-Corduroy Down Jacket

A down jacket in corduroy sounds like designer group-think gone wrong, and yet it works. Plush brown cord replaces the usual crisp-packet nylon, quilted in broad channels over a 75/25 fill, with a stand collar and a boxy cut roomy enough to house some knitwear.

It looks at home in a British pub, which no technical shell has ever managed to accomplish.

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The Best Sport Coat For Men To Invest In

The sport coat is tailoring let off the lead: no matching trousers, no wedding, just a jacket that sits over a crew neck and preppy OCBD as though it was always meant to.

What you want is texture. Think tweed, flannel, suede or a decent check, with very little structure so it feels inherently casual. If it feels remotely like one half of a suit, do it a favour and reunite it with the other half.

MR P. Suede Suit Jacket

Mr Porter’s own brand – MR P. – is like an industry secret, quietly producing top-quality menswear classics at a brilliant price point, as evidenced by this stunning chocolate suede blazer with its notch lapels, patch pockets, soft drape, and subtle seams offering tonal variation.

It is the perfect textural garment to elevate your weekend fits, pairing nicely with neutral knits, denim shirts, and cream jeans or chinos.

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Paul Smith Prince Of Wales Checked Wool-Blend Blazer

The Prince of Wales check was popularised by a king who abdicated, which makes it the ideal jacket for walking out of meetings. Paul Smith has made this version in Italy from wool with a hint of cashmere, and the check gives a plain navy knit or white Oxford something to talk about.

It’s also the perfect foil for layering over a bold-tone cable knit and button-down shirt when you want to lean into its preppy side.

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The Best Men’s Suede Jacket Worth The Money

Suede is leather that has decided to be charming. It’s also prone to weather-borne catastrophe, so its window of utility is reasonably narrow. That said, it is the ultimate signifier of taste, not to mention financial clout, while bringing a healthy dose of texture and tactility to spring and autumn looks.

Look for a tight, even nap, real horn or solid metal hardware and a good-quality lining. Take care of it and great suede will only improve with age.

MR P. Leather-Trimmed Suede Jacket

If you like your jackets workwear-inspired but still want a bit of polish, then MR. P’s leather-trimmed suede jacket couldn’t be a better fit. Crafted from a soft suede in punchy mustard tone, it comes in a regular, slightly boxy fit and quilted for warmth, so you can layer it over a tee and still feel toasty.

A snap-button placket conceals the zip fastening, giving the jacket a clean finish. The large flap pockets and a contrasting full-grain leather collar underline its utilitarian heritage, but this jacket will pair with tailored trousers as easily as it will with denim.

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Hartford Dickson Suede Jacket

Hartford has been dressing Parisians in its particular brand of nonchalance since 1979, and the Dickson is that attitude rendered in brown suede.

A zip front and clean, unfussy lines mean it styles like a dream. Throw it over a simple white tee in spring, or layer it with a denim button-down shirt and cashmere crew neck in autumn, and let the jacket’s rich caramel tone do all the talking.

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The Best Cashmere Jumper For Men To Invest In

In the last few decades, cashmere has gone from something exclusive to a widely available fabric. As a result, quality has broadened significantly, so it’s important to understand what you’re buying.

Ply is a key characteristic and refers to the number of yarn strands twisted together. More ply generally means more warmth. Fibre length matters even more: long fibres soften with age, while short ones can pill almost immediately.

So if you’re wondering why one cashmere sweater is vastly more expensive than another, there’s your answer. A quick test is to squeeze it: good cashmere springs back, while the cheap stuff just sits there sulking. Read more in our cashmere pieces guide.

Ghiaia Cashmere Half-Zip Sweater

The half-zip has been enjoying something of a renaissance in recent seasons after years as the business bro’s go-to knit, thanks in part to luxury brands rendering it in cashmere.

One such label is Italian-Californian Ghiaia Cashmere, which uses artisans at its family-run Italian mill to create beautifully refined garments. This half-zip is subtly ribbed for a textured finish and makes excellent weekend fodder for sophisticated, relaxed looks.

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Begg x Co Heriot Cashmere Sweater

Begg x Co has been making cashmere in Ayrshire since 1866, long enough to have stopped needing to prove anything. And while it remained something of a best-kept secret among the Scots for decades, the brand is now getting the recognition it deserves.

The Heriot is a plain crew neck and makes no apology for it: no logo, no gimmick, just Scottish know-how. Slip it under a sport coat, or over a shirt with a popped collar, for a look you’ll still be rocking in 2036.

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The Best Heavyweight Knit For Men

Some knitwear is layered; some knitwear is the layer. A heavyweight cardigan does a jacket’s work through October, then slides underneath a substantial overcoat when things turn Siberian.

There are two ways you can go with heavy knits: loose, chunky styles that are all about the pattern, or dense, tightly knitted versions, such as heavy ribs, that function like personal radiators. See also our best knitwear brands.

De Petrillo Ribbed Merino Wool And Cashmere-Blend Cardigan

De Petrillo is Neapolitan, so it believes comfort and elegance are the same thing and finds your surprise faintly touching. Yes, Naples isn’t the first place you think of for ‘chunky knit weather’, but De Petrillo has nailed this one.

A deep ribbed merino and cashmere blend brings warmth without excessive bulk, while the soft neutral tone gets along with navy, grey and brown alike. Wear it in place of a blazer and nobody will argue.

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Drake’s Shawl-Collar Ribbed Wool Cardigan

Rib-knitted in Scotland from properly substantial wool and fastened with knotted-leather buttons, this is Drake’s answer to the blazer on dress-down days.

The shawl collar frames an Oxford shirt or plain tee with equal decency. Wear it with grey flannels or straight-leg khaki chinos and feel, briefly, like a novelist with a generous advance.

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The Best Men’s Wool Overshirt To Invest In

The overshirt, or shacket if you’re going to be rude, is the most useful garment nobody can adequately define: too heavy to be a shirt, too light to be a jacket, and worn when the weather can’t make up its mind either.

The investment version is wool, dense enough to hold its shape and trim enough to slip underneath an overcoat. Read our autumn wardrobe essentials for more on this enigmatic layering piece.

Caruso Houndstooth Brushed-Wool Overshirt

Caruso’s Parma factory spent decades making tailoring for other labels, so it has had plenty of opportunity to perfect its own. This houndstooth overshirt is cut from pure Italian brushed wool in a relaxed silhouette, with a satin lining that lets it slide over a knit without a fight.

The reverse-pleat pockets are a beautiful touch too. Layer it over a cream cashmere roll neck for some old-money sophistication.

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Portuguese Flannel Wool-Tweed Overshirt

Portuguese Flannel has built its name on proving that good cloth needn’t cost the earth, and this is one of its most persuasive arguments. Grey mélange tweed, woven from pure wool by Portuguese artisans, is cut along utilitarian field-jacket lines and lined in satin.

At £225, it’s the easiest investment here to justify to anyone.

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The Best Grey Flannel Trousers For Men

Grey wool flannels are among the most dependable trousers in menswear. The cloth should be brushed, soft and slightly matte, with a crease that recovers after a night on the chair.

A percent or two of stretch is forgivable, but steer clear of polyester cocktails sold as wool because you simply won’t get the same longevity. Flannel has a lovely natural drape, so make the most of it with straight- and wide-leg styles, or tapered options with pleats for a roomier fit.

Brunello Cucinelli Pleated Virgin Wool-Flannel Trousers

Candour time: £1,000 is a great deal of money for trousers. But these are pure virgin wool flannel, made in Italy, double-pleated and tapered, with a drawstring waist that means you’ll wear them on a Sunday as often as at a Tuesday meeting.

Loafers one day, trainers the next. That’s where the cost-per-wear maths starts to work and the guilt starts to fade.

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Lardini Wool And Cashmere-Blend Flannel Trousers

Lardini makes tailoring in the Marche region of Italy for half the labels you’ve heard of, and saves some of its best work for its own name. This Italian flannel is mostly wool, with 10% cashmere for softness and a single percent of stretch for ease.

The drawstring keeps things relaxed, but the considered cut and cloth make sure they never look off duty.

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The Best Selvedge Denim Jeans For Men To Invest In

Selvedge denim is the only garment that improves through neglect. Woven on old shuttle looms, it moulds itself to you over months of wear, creasing where you sit and fading where you move, until your jeans become a biography no one else could have written.

‘Rinsed’ means one soak to remove shrinkage, not a factory-faded shortcut. Just beware of sitting on white or cream sofas straight after purchase. New indigo-dyed denim has a habit of embarrassing you.

OrSlow 107 Slim-Fit Selvedge Denim Jeans

OrSlow makes its jeans in Japan using specialised processes and locally sourced materials, taking 1950s shapes and styles as a reference. The 107 is a slim, straight, mid-rise five-pocket jean in selvedge denim with contrast topstitching.

A word of warning: they fit very small, so go two sizes up and spare yourself a humiliating afternoon and the rigmarole of a return.

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3sixteen Classic Straight-Leg Rinsed Selvedge Jeans

3sixteen cuts its jeans in the USA from Japanese selvedge, and the Classic Straight is a vintage-inspired cut with a high rise, roomy thigh and slight taper below the knee.

They’ve had a single rinse, so the shrinkage is done and the indigo largely untouched. Wear them hard for a year and the fades will be entirely, unmistakably yours.

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The Best Goodyear-Welted Boots For Men

Boots are where money goes to die, unless you check the construction. A Goodyear welt stitches the upper to the sole via a strip of leather, allowing a cobbler to resole them again and again.

When you’re paying north of £1,000 for a pair, this detail really matters. With adequate leather care and the occasional resole, great boots can last decades. See also our guide to the best new boot styles.

John Lobb Lawry Leather Chelsea Boots

If the likes of Mick Jagger made the Chelsea boot a rock star, John Lobb makes it a gentleman again. The Lawry is handmade in Northampton from polished brown calfskin, with an almond toe and a Goodyear welt, so it can be resoled for decades.

Measured per wear over 20 winters, it may well be the cheapest thing in this article. Pair them with white denim at the weekend to really show off that incredible leather patina.

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Majordome M11 Cross-Grain Leather Chelsea Boots

Made in Spain and exclusive to MR PORTER, the M11 is a Chelsea boot that has clearly been briefed on British weather. Black cross-grain calfskin shrugs off scuffs, a storm welt keeps the rain out and a lightweight Goodyear-welted Vibram sole grips wet pavements with conviction.

They fit large, so take half a size down.

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In partnership with MR PORTER – words and opinions are Ape’s own.