Then in 2012, Hedi Slimane took the reins at SAINT LAURENT, reviving a rebel grunge aesthetic with high-fashion versions of skinny jeans, double riders and sleek harness boots. Almost overnight, the heritage movement vanished. Today, even streetwear is giving way to bohemian patchwork (à la BODE), 1980s-inspired tailoring (SAINT LAURENT) and a full-fledged westernwear revival.

With the heritage movement now feeling like ancient history, it has become fashionable to question whether style can ever be timeless. “Harrington jackets look stupid now,” Jonah Weiner recently wrote in Blackbird Spyplane. “The implications here are profound because Harrington jackets are supposed to be a fully enshrined garment in the so-called ‘timeless’ menswear pantheon.”

Weiner points out that even the humble white shirt is “subject to myriad historical contingencies and shifting norms,” as cut and materials change by the decade. If you show up to the office nowadays wearing a spearpoint collar in 1970s proportions, someone will make a Bee Gees joke.

Before launching the brilliant fashion podcast Articles Of Interest, Avery Trufelman covered architecture for 99 Percent Invisible. In a lecture about “design drift,” she observed that architects often strive for a timeless quality in their work, designing buildings meant to endure both physically and aesthetically. “But from a historical perspective, I’ve seen that everything is a product of its time,” she said. “To survive, it gets modified. Or attitudes around it shift. Or it dies and fades away. So, what I’ve learnt from studying the staying power of architecture is that everything changes, and nothing stays the same.”

To some extent, this is true – culture is never static. Since humans are always creating, anything made today will inevitably be tethered to a specific time, place and context, even if that timeline stretches beyond a single lifetime. If you go back far enough, men once wore animal pelts, togas and frock coats, all of which have disappeared.

However, I know timeless style is possible because I’ve seen it. The effortlessly suave Luciano Barbera – whose father founded the legendary Italian mill Carlo Barbera – has worn the same soft-shouldered Italian tailoring made from English-inspired fabrics his entire life. Similarly, there’s a photograph of Japanese menswear figures Yukio Akamine and Yasuto Kamoshita hanging out with their friend and tailor Antonio Liverano in the 1980s, all three men wearing the same Florentine suits they do today. And what about Ralph Lauren and the stylish figures around him, such as Doug Bihlmaier and John Wrazej, who have always worn the same clothes?

In an interview with The Hogtown Rake, menswear writer G Bruce Boyer described himself as a prisoner of his youth. “When I was a young man – 12 to 20 – I experimented with all sorts of dress, but more and more drifted to American Ivy Style clothes with a British influence.” Boyer has long championed things such as soft shouldered suits, English tweeds and Oxford button-down shirts. In his books Elegance (1985) and Eminently Suitable (1990), some of the tailors and clothiers he named have been lost to market forces. However, his advice on how to build a tailored wardrobe remains as relevant today as when the titles were first published.

Boyer even has the receipts to prove the steadiness of his style: tucked inside one of his brown glen plaid jackets, there’s a sewn-in label with the lines neatly typed out: “9/5/83, Bruce Boyer Esquire”. The former Town & Country editor wore this jacket through the period of 1980s power suits, 1990s business casual, early 2000s slim fit and even after classic tailoring was declared dead.

Timelessness isn’t limited to dark worsted suits or Oxford button-down shirts, nor does it require dressing in the anonymous grey sweaters and beige chinos immortalised in endlessly reposted images of Steve McQueen and John F Kennedy. Designer Rick Owens has refined his style over the decades, yet his aesthetic has always revolved around ominous, globular forms that blend decayed glamour with the socio-sexual underworlds of Los Angeles.

Similarly, Yohji Yamamoto has long cloaked himself in fluid black garments, exuding mystery, melancholy and rebellion. But how do we reconcile these seemingly contradictory ideas? The answer is simple. Timelessness is achievable when someone possesses three things: self-knowledge, confidence in their taste and an understanding of culture.

In his 1979 book Distinction, Pierre Bourdieu argues that our notions of good taste are nothing more than the preferences and habits of the ruling class. His theory helps explain much of early 20th-century fashion, when figures like the Duke of Windsor popularised belts, turned-up cuffs and a soft British tailoring style known as the drape cut.

Yet as the century progressed, style influence shifted. Style is no longer dictated by just those with financial capital; it’s also shaped by those with cultural capital, such as musicians, artists, countercultural youths, outdoorsmen and everyday working-class people.

Understanding this history is key to grasping timelessness. Even as fuller silhouettes gain popularity, skinny black jeans paired with a black double rider and black boots will always look great, thanks to figures like Lou Reed and the legacy of 1980s punk. Likewise, a trim suit with cigarette trousers can channel 1960s mod cool even in more contemporary cuts (let CELINE HOMME be your guide). These aesthetics endure because they connect to groups that have always wielded cultural capital.

Whenever people discuss timelessness in fashion, the debate is often framed as a battle between classic tailoring and fleeting trends. Navy blazers and penny loafers may be classic, but they won’t become true wardrobe staples unless they resonate with you.

Take Monty Don, the British horticulturalist who presents Gardeners’ World on the BBC. He has long favoured battered thornproof tweeds, cotton-drill chore coats and high-rise corduroy trousers with pockets deep enough to hold a penknife, hanky and string. His style is charming not because it adheres to some rigid notion of timelessness, but because it’s both functional and steeped in a tradition of gardeners’ attire that stretches back over a century. More importantly, he’s a man who knows himself and trusts his taste, regardless of where fashion’s currents may lead.

In the early 2000s, the heritage movement helped reframe fashion in a way that encouraged men to take dress seriously. But as many hopped onto the hedonistic treadmill in the years that followed, some began to question whether timelessness was just a chimera. Timelessness is certainly more complicated than shopping from a checklist of wardrobe essentials, but it remains a crucial part of the conversation. Without the ability to rise above trends, personal style becomes impossible.