Knitwear is knitwear, right? Wrong, says this wool-blend, patchwork, shawl-collared cardigan from RRL. Inspired by Mr Ralph Lauren’s Colorado Ranch, this belted sweater has workmanship and style in spades. Though it’s absolutely a look, like most of the pieces that come out of this brand, it eschews trend therefore ensuring it will be a cardie that you can wear over, and over, and over again.

There are few items more worth their weight in gold than perfect navy trousers. These, from UMIT BENAN B+, may be just the pair you’ve been looking for. They are crafted from cotton, and so have heft and structure, but sport the front pleat and cuffed hem of their woollen cousins. They also have a couple of workwear details – a tool loop and pocket along the back of the left leg – meaning you can wring hundreds of outfits out of this one item.

Is your coat collection missing a peacoat and a shearling? Kill two birds with one jacket with this luscious Yves Salomon. The classic double breast works perfectly with the fuzzy notched collar and seaming of a shearing. We particularly like the shorter cut of this coat – lending the peacoat silhouette a cooler, younger vibe.

It’s not unlikely that you (or your father, or his father) have owned a Fair Isle sweater at one point in your life. The Scottish heritage style, made popular in the 1920s by the then Prince of Wales, is seasonally ubiquitous. Leave it to The Elder Statesman to ramp it up with bright colours, geometric shapes and their glorious cashmere yarns. This is a sweater worth saving for your grandkids – invest in moth repellent now.

As tends to be the case with anything bearing a Loro Piana label, what elevates this overcoat above the ordinary is the quality of the fabric: a blend of wool, alpaca and cashmere that has been brushed for an exceptionally soft finish. But let’s not fail to mention the colour, too, a deep, mossy green that’ll set you apart from the navy and charcoal-grey masses this winter.

Bottega Veneta’s intrecciato woven leather is one of the most iconic motifs in modern luxury, acting as a symbol of the brand’s commitment to craftsmanship as well as its understated approach to style. And it’s never put to use better than in this sleek leather bag. A timeless accessory that’ll stay with you for years.

Talk about built to last: the model for these boots – an Alpine hiking shoe from the John Lobb archives – is 80 years old, so they’re more or less guaranteed to stand the test of time. And the brand’s famously high construction standards ensure that, taken care of properly, they’ll withstand the wear and tear of daily use.

Berluti’s Venezia leather is the stuff of legend, polished and burnished to a deep, rich finish that more closely resembles antique mahogany than your everyday leather. More commonly associated with the Parisian luxury brand’s footwear, it nonetheless serves just as well on its small leather goods. This billfold wallet is a prime example.

The months and years will pass, but a perpetual calendar watch takes it all in its stride. Engineered to correctly display the length of each month without adjustment, it is a mechanical marvel designed to outlast its wearer. Jaeger-LeCoultre’s Polaris Perpetual Calendar combines horological expertise with mid-century tool-watch pedigree and a dark-blue gradient dial to deliver a watch that’s all things to all people. The four sub dials display the month and year, day of the week, stage of the lunar cycle and date of the month, clockwise from 12.

The spade symbol has had many meanings over the centuries. On a deck of cards, it is usually taken as a reference to the nobility and military classes, thanks to its similarity to the head of a pike or halberd, common items of medieval weaponry. It can be used to represent age, wisdom and good fortune, power, success and death. Some see it as a leaf from the tree of life. Foundrae has engraved its 18k-gold spade necklace with radiating lines to signify overflowing and abundant resources. Next to it sits a malachite crescent, taken to denote Earth.

Woven in Italy on a decades-old shuttle loom from the finest cotton, these straight-leg indigo-blue denim jeans are the platonic ideal of the world’s most famous trouser. Five pockets. A button fly. Orange contrast stitching. Flawless cuffs. These are the jeans other jeans dream about – the age-old workwear staple elevated to the most luxurious heights thanks to the care and attention lavished over every inch. An investment not just for this winter but every one to come.

Tie it. Loop it. Toss it rakishly over your shoulder. OK, so a scarf may not have inexhaustible modes of use, but a good one can make all the difference once the weather demands it. It’s the finishing touch to a winter outfit, the first and most effective line of defence against the elements, but can also be the centrepiece of a fit, drawing the eye (or even better, framing your handsome features, you snug devil). This cashmere check number from Burberry will stand the test of time.

Sometimes, all you need to feel better about the sartorial transition into winter is something that’ll make you look – and feel – instantly more put-together. Take this Canali blazer, which will look just as sharp when styled as part of a full suit as it will if you break it up with another pair of formal trousers.

Few things say “cosy season” quite like a plush hoodie, especially if it’s as cool as SAINT LAURENT’s. Backed in soft fleece, it’s detailed with an almost imperceptible take on the French house’s moniker, which is embroidered in tonal grey thread across the chest.

We might not need to wrap ourselves in a big puffer jacket just yet, but we’ll tell you what’s smart: prepping ahead of the impending mercury drop so you don’t find yourself unprepared. There’s no better way to do so than investing in outerwear that’s practical, warm and stylish – you can’t go wrong with Moncler’s collaborative puffer with Mr Pharrell Williams.

If you’re anything like us, when browsing for sartorial investments, you’re looking for something that stands the test of time and that you can style with pretty much anything you already own. We feel like you would appreciate a pair of loafers – for instance, this CELINE HOMME version, made from buffed brown leather and detailed with the house’s retro-inspired hardware, should be at the top of your Wish List.

Sunglasses for autumn? Yes, really. Sure, the sun might not be beating down on us anymore, but don’t be fooled: those sneaky UV rays are still wreaking havoc from behind the clouds. More importantly, they look great all-year round, especially when they’re from if-you-know label Jacques Marie Mage, which engineers its wares in Japan. Here, it has teamed up with the Yellowstone Forever project for a pair of smokey square frames that’ll add a touch of after-dark mystery to any outfit.

Take note: this is not your average flannel shirt. This right here is the work of God’s True Cashmere (brainchild of Mr Brad Pitt and his go-to spiritual guru Ms Sat Hari Khalsa), which creates easy-going, everyday pieces from the world’s most sought-after fabric. As such, this piece is spun from 100 per cent cashmere – nothing less and nothing more – and features snap fastenings made from none other moonstone. Layer it over T-shirts for a 1990s grunge look, albeit one that oozes luxury.

This season, the king of quiet luxury delivers a suitably autumnal alternative to your classic leather low-top. As is customary, Brunello Cucinelli eschews flash in favour of quality ­here – namely the supple leather uppers and robust rubber soles that promise to better with age. Better yet, these arrive in a rich chocolate-brown shade that will complement everything in your wardrobe, so you can finally give your knackered white sneakers a rest.