There comes a time every year when a man must decide which shoes to invest in for the season ahead. It may not be quite as much of a landmark as, say, switching careers or popping the question, but your decision could have significant consequences for the rest of your wardrobe. As with a winter coat, footwear has the power to make or break an entire outfit and, with that in mind, it’s wise to tread carefully.

While you’re weighing up your options, we’ve put together a list of our favourite pairs, to ensure you’ll stride into autumn on the right foot.

To the relief of most, menswear has spent the past 50-plus years emancipating itself from its own rigidly imposed and, in many cases, quite silly rules. There are, however, some mandates that die hard. “Never wear brown in town” might sound delightfully quaint, but there are still a number of men who cling to this idiom. Pay these naysayers no mind; the infrequently seen brown Oxford is a considered and characterful substitute for black – particularly, we should note, when paired with a navy suit. And, with its rich, mottled leather uppers and refined cap-toes, this Goodyear-welted rendition from English firm Tricker’s is especially charming.

Unlike in the realm of womenswear, where trends can seemingly turn on a dime, menswear’s long and winding history is characterised by subtle shifts. And though its tectonics have been more active in recent decades, there are certain items of clothing that need little editing. Derby shoes are just such an item. Thanks to the endeavours of a select group of designers, they’ve evolved into something sturdier in the past couple of years, but the template is largely unrevised: black or brown leather or suede, open lacing (this is the idiosyncrasy that differentiates them from Oxfords) and a considerable sole. Then Mr Dries Van Noten has a go and renders them in a moody shade of grey. A subtle shift, yes, but one that makes a world of difference. Bravo.

Whether or not you have a stomach for caricaturised violence, boilerplate female stereotypes or, erm, shoeless feet, it’s hard to get through 20 minutes of Mr Quentin Tarantino’s Once Upon A Time In Hollywood and not come to the silent, but profound realisation: “I need to get myself a pair of cowboy boots, sharpish”. Designers seem to have pegged just in time that this would be the average cinemagoer’s takeaway and have dutifully supplied MR PORTER’s shelves with a bounty of Western-worthy iterations. This well-heeled pair, from SAINT LAURENT, borrows from classic Chelsea styles (note the ribbed sides and pull tab), but adds an elongated pointed toe and Cuban heel. Wear them with jeans and your best drawl.

Few cordwainers can match Church’s shoemaking pedigree. The brand was founded in Northampton in 1873 by Mr Thomas Church, but its history stretches back to 1675, when his great-grandfather mastered the trade. Now under the remit of the Prada Group, the brand walks the fine line between tradition and timeliness, often satisfying both orders. These McPherson brogues, for instance, come in a hardy “Highland Grain” leather with classic wingtip perforations, but are constructed on the shoemaker’s 133 last, which makes for a slightly more contemporary rounded toe and heftier profile. Just right for this time of year, then.

Today, there are two main schools of loafer thought: the Italian and the English, with the former offering a slightly more casual silhouette and the latter famed for more structured, sturdier styles. But you largely have the Yanks and the Norwegians to thank for their induction into the male wardrobe. Known as the Bass Weejun in its native Norway (and still sold today by the American brand G.H. Bass & Co), the sartorial rumour mill has it that penny loafers were popularised Stateside by Mr F Scott Fitzgerald and his well-dressed associates, before later becoming part of the scenery on Ivy League campuses. This was around about the time Gucci introduced its now paradigmatic horse-bit loafers – 1953 to be precise – which have experienced a recent renaissance under the direction of the house’s current head, Mr Alessandro Michele. One of a score of his tinkered designs, this unapologetically chunky pair in deep autumnal burgundy fulfils this season’s stompy requirement and then some.