Whether it’s waging war against the wind with your umbrella or attempting to navigate your way around lake-like puddles, we’re willing to bet that your morning commute is slightly more of an adventure now than it was a few months ago. And, we’re sorry to say, it’s only going to get worse from here on out. Winter is well on its way. But instead of abandoning all hope, there is some sartorial preparation ye, or indeed you, can do to negate the effects of cruel weather. It all starts from the ground up, with sturdy shoes or boots. And these are the pairs that are up to the job.

Strictly speaking, desert boots are summer-specific footwear. The clue is right there in the name: they were first introduced to the UK by Mr Nathan Clark (of British retail stalwart Clarks) who, while deployed in Burma during WWII, spotted that the men there wore lightweight boots equipped with a crepe-rubber sole for grip. Warm-weather associations aside, their usefulness can extend into the cooler months if you opt for a chukka boot – identical in style, but with leather soles in lieu of rubber. Then there’s Italian brand Officine Creative’s iteration above, which offers the best of both worlds: they’re fitted with traditional crepe soles sandwiched around a more robust layer of leather for firmer footing. Perfect then for bridging the gap between the seasons.

One of the most important developments in menswear – specifically men’s footwear – in recent years has been the relative increase in the size of soles. True, the advent of the so-called “chunky” shoe is hardly a new phenomenon, but this season it seems like everyone’s wise to it. This is a very good thing in our books: notably, a sturdier sole is clearly practical this time of year, when the chances of encountering a puddle at any given time increase manifold. The classic Derby has received the most attention in this respect – with Prada, ever at the vanguard, leading the charge – but boots have been given a similar treatment of late: the lug-soled example on the left, from our very own Mr P. line, for instance, is the paradigm to aim for. If we do say so ourselves.

There’s something comforting about an item of clothing that has barely changed for a hundred years or more. Perhaps it’s the knowledge that you’re wearing something immune to the whims of fashion. Suits fall into this category, as do lace-up boots, which are, we admit, a little older: they’ve existed in essentially the same form since the middle ages. Bootmaker John Lobb, though not quite as mature, boasts a long and storied history – the London outfit has been making shoes like this pair since 1866, and its methods have altered very little over the years. This Alder pair is modelled after a ski boot from the 1940s unearthed from the cordwainer’s archives. The two-tone marbled patina does much to recommend them, as do the comfortable padded collars and watertight storm-welted construction. Follow our lead and wear them with cropped tailoring to show them off in all their glory.

Speaking in sweeping generalisations, summer style is usually defined by silhouette – shorts, T-shirts and so on – whereas autumn and winter dressing is a shade more nuanced: when you’re wrapped up in knits, a coat and scarf, a lot of what makes it special comes down to texture and tone. Suede boots, for instance, become a far more appealing choice when the leaves begin to fall, and this autumnal Edward Green pair in particular. Similarly, pay attention to leather treatments when you’re browsing for shoes this season – the unique patination on the uppers of these George Cleverley lace-ups will fit right in with fallen foliage.

Hiking and trekking-appropriate footwear has been on the trend radar for a while; forecasters would suggest they’re a byproduct of the craze for all things technical currently dominating menswear. It’s a happy development. Practical shoes, after all, are what we’re all after come wintertime. If you’re looking for the most refined take, run, don’t walk, to Italy. This pair from Brunello Cucinelli, the master of Umbrian luxury, is a fine choice: they’re hand-crafted from richly-patinated leather and stacked on tough-as-nails commando soles. You’ll get a treat when you slip them on, too – they’re fitted with toasty shearling linings to negate the effects of plummeting temperatures. Who said you can’t be sensible and stylish?

Chelsea boots are the bad boy of the boot world, a fact that SAINT LAURENT has regularly used to its advantage over the years. A little while ago, the label introduced a pair that seem to embody the brand’s entire aesthetic spirit and philosophy. The Wyatt is a Chelsea boot, yes, but it is also so much more than that: a slightly elevated heel, a sleek elongated toe and, sometimes, a Western-inspired harness add up to a whole lotta shoe. It’s become as covetable as the house’s signature slim-fit jeans and leather biker jackets. This season it comes in an I’m-with-the-band python and black leather combo. Incidentally, they’re the perfect match for those aforementioned jeans and jacket.

Thankfully, the antiquated mores of menswear are largely a thing of the past; it is, for example, perfectly acceptable these days to wear brown in town and not find yourself on the receiving end of stern glares from your fellow commuters. That being said, brown shoes are still generally considered slightly less smart than their black equivalents. How you choose to wear them, then, makes a world of difference. Here, Dries Van Noten’s hefty Derby shoes (see above for reference), which you might initially be tempted to reserve for weekends, are rendered smart enough to wear to holiday parties and similarly festive occasions thanks to the addition of immaculately tailored camel-coloured trousers, also (and unsurprisingly) by the same designer.