Men who are just beginning to build a better wardrobe frequently make the mistake of approaching this process from one of two extremes: either they treat dressing as though it is a purely creative endeavour or as if fashion is subject to universal, immutable laws like physics. Both approaches are likely to send you down the path of creating incoherent outfits.

Instead, think of dress as a kind of cultural language. Just as there are thousands of languages, each with its own grammatical rules, there are also thousands of aesthetics with their own ideas about fit, proportions and styling. Style is neither entirely free of rules nor constrained by a single set of them. It’s about choosing a language and then learning how to speak eloquently within its parameters. Whether we like it or not, our clothes say something about us. Taking control of that communication starts with learning about the language of clothing.

The easiest way to do this is to pay attention to culture, both historical and contemporary. If you’re interested in rugged, outdoorsy brands such as Patagonia, look up photos of the Stonemasters, a motley crew of LSD-fuelled rock climbers during the 1970s. For something more polished, read about the soft-shouldered, dart-less form of tailoring that mid-century Ivy League students and Black jazz musicians made famous. Alternatively, look at how certain archetypes have been represented through time: the artist, the worker, the dandy, the rebel and the intellectual.

You don’t have to mimic these looks entirely, but by understanding the themes that tie particular aesthetics together, you can create stylish and culturally legible outfits. Collect photos of outfits that inspire you, read about culture and pay attention to how costume departments dress characters in films and TV shows. This will give you a better understanding of the cultural language of clothing, which will better allow you to express your personal style.

The internet is full of lists of must-have essentials that should be in everyone’s wardrobe. Such lists are often too dictatorial, pushing a singular aesthetic on everyone, regardless of their age, personality or lifestyle. A better approach would be to identify useful, versatile things that allow you to explore your taste so that you don’t have to reinvent your wardrobe whenever your interest takes an unexpected turn.

Most men could use a pair of dark, slim-straight jeans that can be paired with everything from navy blazers to military field jackets; a stout grey sweatshirt that can be teamed with Ivy style or streetwear; a Shetland knit that can sit comfortably alongside Margaret Howell, Dries Van Noten or Engineered Garments; light blue button-ups that work with Italian tailoring or American workwear; and a solid rotation of at least three pairs of shoes, such as white sneakers, brown boots and brown loafers (or whichever three you think suit you).

It’s not that these items will necessarily stay in your wardrobe forever, but that they’re easy to find, comfortable and not too financially out of reach. They also do the important job of allowing you to experiment – and experimentation is critical to developing personal style.

Once you have a solid foundation, go explore. Don’t get hung up on versatility; splurge on the occasional showpiece. Buy a beautifully tailored, soft-shouldered suit and see if you wear it with enough regularity before committing to another. Try an offbeat Japanese workwear brand to see if that aesthetic is right for you.

The important thing is to give yourself time – seven years, minimum. Developing a sense of personal style is an evolutionary process that requires you to be willing to make mistakes. Don’t overly commit in the beginning; shop slowly and let your experiences guide you. Find what excites you, not just on day one but in a few years’ time.

In his 1721 book Lettres Persanes, Montesquieu lamented that fashion moved too quickly for him to capture it in writing. “What is the use of my giving you an exact description of their dress and ornaments?” he cried. “A new fashion would destroy all my labour, as it does that of their dressmakers, and before you could receive my letter, everything would be changed.” Even in the 18th century, people easily got bored with the familiar and became fascinated with the novel.

Neophilia is the destroyer of personal style because you never end up wearing anything long enough for it to feel like it’s part of you. Like old friends and familiar places, old clothes bring a special comfort that only time can reliably provide. There’s something wonderful about threadbare tweeds, naturally faded jeans and well-worn brown leather shoes that have developed a patina to make them look like the surface of an old mahogany desk. These things exude personal style, if only because they’ve been personalised through wear.

This doesn’t mean that you have to avoid trends. On the contrary, trends can be like classrooms, making us reconsider things that we may have overlooked. In the past five years, the revival of chunky sunglasses, sleazy rayon shirts and flared-legged jeans has recast the “decade that taste forgot”. Similarly, the rise of fuller silhouettes – without necessarily displacing slim-fit clothes – means that people can find styles that actually suit their bodies and personalities. However, the important thing is to use these moments to learn why a particular style is special and be confident enough in your taste to keep wearing something even after a trend has passed.

It does not matter that fashion writers are now speculating whether the adidas Samba trend is burnt, as the shoe’s appeal should have never been about celebrities or influencers, but rather its more enduring associations, such as the Samba’s place in British football and American hip-hop culture. Beware of the opinions of people whose material condition depends on you replacing the “new” with the “newer new”.

Fashion historian Mr James Laver once observed that fashion signals our belonging to specific groups while also showing our individuality within those groups. In that sense, personal style is often about adjusting an aesthetic at the margins so that it remains culturally legible while also reflecting our uniqueness.

There’s no formulaic way to do this (otherwise, it wouldn’t be personalised). The best approach is to let this personalisation emerge naturally over time. Mr Eugene Rabkin of StyleZeitgeist said he went through a phase of wearing various designer brands before eventually landing on Rick Owens, an aesthetic that he has mostly pared down to simple black jeans, drapey T-shirts and certain outerwear pieces from the label.

A suit-wearing friend who recently became a father told me he had to give up his grey flannel trousers in favour of more durable, washable pants such as white jeans and olive fatigues, which he sometimes dresses up with Oxford cloth button-downs and navy sport coats. A navy sport coat with olive fatigues may be an unusual combination, but it reflects his actual lifestyle. Over time, your style will naturally emerge as you repeatedly grab for the same things.

There’s an obvious paradox here: fashion is a way for us to both explore and express our identity. When trying on different aesthetics, some outfits may feel like costumes until they feel like natural extensions of our character. People are also complex – they have distinct and sometimes contradictory sides. Your style may be an amalgamation of different aesthetics worn at different times, depending on your environment or mood.

There are multiple paths up the mountain. But you can make this process easier by paying attention to the cultural language of clothing, being open to exploration, keeping a wary eye on neophilia and allowing your personal style to emerge from experience.