Of the many boot styles that populate the ankle-grazing footwear category – hikers, jodhpurs and hobnails, oh my! – the Chelsea is the undisputed king. First appearing as a riding boot in the 19th century (the characteristic elasticated sides and pull tab were designed to ease the process of pulling on and off between canters), the style has since become synonymous with low-key winter elan.

There are, of course, manifold variations on the Chelsea boots available to buy these days, but the constituent elements always stay the same. A dark chocolate-brown leather boot with a chunky commando or leather sole is arguably the way to go if you plan on buying one forever pair. That way, you can wear them as easily with jeans at the weekend as you can with tailored garments at work. The best place to source this style of boot is either from Manolo Blahnik or R.M.Williams.

If you tend to swim in the more casual end of the sartorial pool then look to the chocolate-hued suede Chelsea boots made by Tod’s, Brunello Cucinelli and FERRAGAMO. Or if you prefer to dress like a stylish undertaker, then the best black leather Chelsea boots can be found at TOM FORD, SAINT LAURENT and Alexander McQueen.

Not all slip-on shoes are built the same. Some occasions call for chisel-toed Neapolitan-style loafers – when you’re attending a summer wedding, for instance. Others demand a classic penny loafer – when you’re cutting your best Mr Paul Mescal impression in jeans and a white tee. There are even moments when boat shoes (technically part of the loafer family) are called for, but I’d be inclined not to include these within the five pairs of shoes you should own. Unless, of course, you also own a yacht.

Instead, your choice of ultimate adaptable loafer should be one that sits somewhere between an ultra-smart chisel toe and an everyday penny. A good place to start would be Gucci, with a pair of the brand’s classic horsebit loafers in brown or tan. They’ll never go out of style and they can just as easily be worn with low-key separates (à la Mescal) as they can with tailoring.

Alternatively, you could opt for a pair of polished oxblood loafers from Mr P. or Loro Piana. I own a pair from the latter brand and they are my perennial go to. The colour works with the full spectrum of shades found in the majority of men’s wardrobes (navy, black, grey, brown and bottle green), while the round-toe shape teamed with the snout-like profile mean they can be made to look as casual or, indeed, formal as you like.

Maybe you’re attending a gala, or perhaps you have a court appearance. Either way, if the dress code reads formal, you’re going to need a sturdy pair of black Derby shoes or Oxfords at the centre of your footwear arsenal.

As a rule, Oxfords (defined by featuring the lace openings under the vamp) are a smarter option than Derby shoes (lace openings on top of the vamp), and round-toe styles tend to be more adaptable to smart and casual situations than those with chisel or pointed toes. A failsafe option, then, would be a pair of heavy-soled black Derbies imbued with some character. You’ll be able to wear them with everything and they won’t make you feel like you work in a bank when you do. And if you do work in a bank, then, well, they’ll make your colleagues leathery with envy. Wins all round.

For the best chunky black Derby shoes, look no further than Bottega Veneta, FERRAGAMO (the Florentine brand’s footwear silhouette has become more muscular under tutelage of British creative director Mr Maximilian Davis) and, of course, Mr P.

It would be easy to advise you, at this point, to buy a pair of classic white tennis shoes from Common Projects or Veja and be done with it. But before taking the plunge, it’s worth considering how you’ll be wearing your sneakers and what you’ll be wearing them with.

Personally speaking, I wear a lot of navy blues, browns and pinks. I also prefer classic tailoring to more casual garments. As a consequence, I’ve discovered – with much trial and error – that my outfits look best teamed with a very thin-soled sneaker, preferably in cream, brown or tan. As such I tend to buy and re-buy pairs of low-slung adidas Sambas from Ms Grace Wales Bonner’s collaborative capsule with the German brand – which are like melted Mr Whippys for the feet – though some classic Sambas or Gazelles would work just as well.

If, on the other hand, you prefer wearing sportswear, you might want to opt for something a bit, well, sportier, such as a pair of Nike Air Maxes or Humaras.

Whichever shape or style you pick, be sure to keep the hue as neutral as possible in order to make the sneakers align with any outfit you choose. Beiges, creams and whites will almost always work well, whatever you’re wearing. And if you can’t decide? Simply go for some serviceable Common Projects or Vejas and be done with it.

We’re living in an increasingly casualised world, as evidenced by the proliferation of cosy slides, slip-ons and mules. If easy-wearing shoes weren’t truly taking over the world, would LVMH have worked so hard to acquire a majority stake in low-key shoe enterprise Birkenstock in 2021? I’m inclined to think not.

When it comes to buying your own pair of sliders, it’ll pay to start your search at the source. Birkenstock’s suede Boston mules should be your go to in the summer months, as they work brilliantly with casual outfits, while the brand’s shearling-lined versions are excellent for shuffling around in the winter.

For something a little zhuzhier, look to Balenciaga’s Sunday mules, which feature paw-like toes moulded into the uppers, or Marni’s furry Fussbetts, which are about as barmy as easy-wearing shoes get, and all the more essential for it – hence I own three pairs of them.