From suede Chelsea boots to leather Derbies, these classic styles will cover you for every sartorial situation.

One of the greatest things about being a grown-up is being able to dress like one and, as our Contributing Editor Mr Mansel Fletcher explains in this week’s instalment of A Gentleman’s Guide, there’s a reason why many of the world’s best-dressed men tend to be… of a certain vintage. As we get older, our sense of style matures with us. We relax into ourselves, becoming less concerned with seasonal trends and more aware of the finer things in life. And there are few things in life finer than a pair of proper, grown-up shoes.

A clarification: when we say “grown-up”, we aren’t referring to shoes with laces instead of Velcro, but to the kind of classic, well-made shoes that need a few miles on the clock to be fully appreciated. We’re talking bench-made Oxfords from John Lobb, for instance, or suede Chelsea boots from Northampton’s Edward Green. These are shoes for men with well-developed tastes, who value quality and timeless design over paying lip service to some passing fad. If you think you fit that description, read on to discover the six pairs we’ve selected as worthy of your attention.

First launched in 1953 and a constant in the Gucci line-up ever since, horsebit loafers are an undisputed design classic. The brass detailing might reference the Florentine brand’s equestrian heritage, but what this shoe really stands for is the jet-set glamour with which the Gucci brand became synonymous during the second half of the 20th century. It’s such a recognisable icon of luxury, in fact, that in 1985 it was added to the New York Metropolitan Museum of Art’s permanent collection. These shoes speak of an easy life, and rather fit the profile of a successful older man at ease with himself and the world. Gucci’s new creative director, Mr Alessandro Michele, is now experimenting with the codes of the house and has reinvented these shoes as, among other things, kangaroo-hair-lined slippers. For the purposes of this article, we’ve erred on the side of caution and plumped for something slightly more straightforward.

Tod’s built itself into a billion-dollar brand off the back of this shoe, so it’s safe to say its style credentials are assured. But what is it about suede driving shoes, ostensibly designed for sitting in the front seat of a classic car, that had such huge global appeal? We’d hazard a guess that it’s something to do with the air of casual effortlessness they lend a man. It is la dolce vita in a pair of shoes, the quintessence of laid-back Italian style. And it’s not just driving; these shoes are made for padding around the piazza or spending three hours over lunch.

Men who are taking their first step into the world of “proper” footwear should begin with a pair of Oxfords, and there are few names in the cobbler’s trade that speak more loudly of quality than John Lobb. In a rich shade of chestnut brown, these are the perfect companion to a navy suit. Do yourself a favour and turn a blind eye to those stuffy, outdated fashion diktats that suggest you ought not to wear brown shoes in town, or that you should match their colour to that of your belt. An over-reliance on rules is one of the clearest indications of a superficial interest in style.

The home of men’s traditional shoemaking is not Milan, Paris or Tokyo, but Northampton, a market town some two hours’ drive north of London. Here, courtesy of one of its most famous cobblers, Edward Green, comes a particularly compelling case for clearing space in your shoe closet for a pair of Chelsea boots. Suede Chelsea boots may be something that are typically associated with rockers (Saint Laurent designs a heeled version that’s found favour with many a wiry, leather-jacketed lead singer), but that’s no reason for older guys to steer clear. They’re not only versatile shoes that work just as well with a suit as they do with dark denim, they hint at a rakish, adventurous sense of style, too.

Don’t be fooled by the suspiciously English-sounding name. J.M. Weston is a French shoemaker through and through, as beloved by heads of state – President François Mitterrand allegedly owned 30 identical pairs of its Blake loafers – as it was by the Parisian post-beatnik tribes of the 1960s, who strolled sockless along the Champs-Élysées in the brand’s most iconic shoe, the 180 moccasin loafer. With its conservative attitude towards design, J.M. Weston is a brand for the traditionalist. These 531 monk straps were designed more than half a century ago, and have been subject to only the slightest changes over the years. But then, why mess with a winning formula?

You can’t miss a Berluti shoe. The 121-year-old Parisian brand applies a special treatment to the leather that leaves it looking like a piece of vintage Chippendale mahogany furniture. Not only is the finished product beautiful, it’s also instantly recognisable to those in the know and marks out the wearer as a man of exceptional taste. In this case, that iconic leather treatment has been applied to a single piece of full-grain hide that has been shaped into an elegant, streamlined lace-up shoe. As with everything Berluti produces, it could hardly be described as cheap. But then, that’s another of the joys of getting older: the experience of suddenly finding yourself able to afford all those things that you longed for as a younger man.