The timeless fashion you're sold doesn't exist. And that's good news.

For most people, classic menswear means a suit, shirt and tie. These and other staples, the trench coat and chinos among them, are often called timeless. Style guides and marketing brochures suggest that a good suit "never" changes and outlasts trends.

"Timeless" gets used so often by so many creators and advertisers that I regularly wonder when it will stop. Just look at old photographs or fashion illustrations: the "timeless" suit of the 1920s looked different from the one of the 2020s. Proportions and ideas of beauty have changed considerably since 1920. Yet the myth persists, kept alive as a sales pitch, sometimes unwittingly and sometimes quite deliberately.

As Derek Guy puts it: “I tend to roll my eyes nowadays whenever someone writes about 'timeless style'” (dieworkwear.com).

In this article, I want to show you why the timelessness we're sold is an illusion, what has actually changed from one decade to the next and how to recognise the pieces that still work across decades.

The myth of timeless elegance: promise and reality

For generations, menswear has had this idea that certain clothes are "classic" and therefore immune to time. A navy Brooks Brothers jacket or a grey three-piece suit in the English style is treated as a wardrobe evergreen. Writers such as Alan Flusser and Simon Crompton often make the case for enduring elegance in their books and blogs.

Flusser, for instance, argues for avoiding extremes: overly fashionable cuts date quickly, while moderate proportions last longer. He praises Ralph Lauren's success for designing classics rather than trends, clothes that don't become "prematurely obsolete" (permanentstyle.com). In the same interview, he dryly observes that "most fashions of the seventies, eighties and nineties are obsolete today", for all the promises of timeless class made at the time.

That is where the promise meets reality. Many people want clothes that will never look out of fashion. But classic menswear has trends too, and it follows them. Even advocates of Permanent Style such as Crompton acknowledge that no style is absolutely timeless. At most, it keeps being reinterpreted.

To an outsider, the classic menswear canon therefore looks unchanged. Those who know it see the small differences. Ethan M. Wong puts it well: “Menswear appears to be a monolith, but only those who know can see the nuance” (alittlebitofrest.com).

Changing proportions: menswear from 1920 to today

A look through the past hundred years shows that what seems like an unchanging suit is really a history of constant change.

In the late 1920s and the 1930s, the drape cut dominated: broad shoulders, a full chest, high-rise pleated trousers and generously rolled lapels shaped the silhouette. These "Golden Age" proportions were long held up as the ideal of classic elegance. Many enthusiasts today, including the people behind Bryceland's and Alex of @freivontrends, still rave about the suits worn by the Duke of Windsor or Cary Grant.

But the post-war years already brought a different look. In the conservative 1950s, Brooks Brothers helped define Ivy League style: the sack suit with natural shoulders, a 3/2 lapel roll (three roll two) and a straight silhouette. It was a deliberate anti-fashion move at the time, marketed as "timelessly American". The 1960s turned the picture around. London's Mod era favoured short jackets, narrow lapels and slim trousers, youthfully rebellious and a world away from the roomy suits worn by their fathers' generation. By then the pattern was clear: what one generation calls classic looks dated to the next.

The cycle reached another extreme in the 1970s and 1980s. Suddenly there were very wide ties and enormous shoulder pads, the power suits of the Wall Street era. In the 80s, Giorgio Armani made jackets soft and oversized, with a low buttoning point and wide lapels. A look that seemed hopelessly dated by the next decade. Flusser comments: “One year you had low gorge, wide shoulder clothing… All of the previous ones were obsolescent” (permanentstyle.com).

In the 1990s and 2000s, menswear first became more moderate, then radically slim again. Think of the skin-tight suits of the early 2010s, Hedi Slimane or the "Mad Men" retro wave, with ultra-low-rise trousers and short jackets pushing a youthful ideal, often at the expense of comfort and classic proportions. They came with stretch percentages that would make an insider trader jealous. Around 2020, the pendulum swung back once more. Higher rises, wider trousers and fuller cuts made a comeback, driven both by high fashion and by retro-minded brands such as Drake's and Bryceland's, which deliberately draw on the 30s to the 50s.

These changes didn't happen in a vacuum. Fabric rationing during the Second World War forced slimmer suits. The youth culture of the 60s and women in the workplace helped shape the power suit of the 80s. Then there were films, musicians and style icons. All of them kept reshaping the image of a well-dressed man. The thread running through it all: nothing is absolute. Every generation decides afresh what "classic" means.

The details: from lapel roll to trouser rise

The overall silhouette isn't the only thing that changes. The details reveal changing ideals too. In fact, the subtleties you have to learn to see are the clearest clues to a piece's age.

A few examples. In the 1930s, jacket lapels were often wide and rolled softly over the top button. In the early 2000s, extremely narrow, sharply pressed lapels were in fashion. The buttoning point moved up and down over the decades, higher on the three-button jackets of the 60s, lower on the double-breasted jackets of the 80s with their deep V. Trouser rise fell from just below the ribs to the hips over the course of the 20th century. By the late 1990s, some suit trousers sat as low as jeans. Now the rise is moving noticeably higher again. Trouser width has followed a similar path, from the wide Oxford bags of the 1920s to the skinny cuts of the 2010s and back again. Then there is shoulder construction, soft and natural on an Ivy jacket, heavily padded on an 80s blazer, and the gorge, the height at which the lapel meets the collar.

Classic menswear isn't a fixed rulebook. It is a set of elements put together differently according to the tastes of the time. What counts as the "right" jacket length or the "correct" tie width has always been in flux.

Put another way, every piece carries the code of the decade it comes from. Lapel roll, buttoning point, gorge, rise, lapel width: that is the code. Once you can read it, you can place a jacket in its decade in seconds.

So is timeless menswear just an illusion?

The version we're sold is. Spend an hour scrolling through old suit photographs and you'll see it yourself. What passed for classic in 1985 was unbearable ten years later. And that 2010s suit sold as a timeless investment now hangs unworn in a wardrobe because anyone can tell at a glance when it was made.

Brands keep using the word anyway because it sells. "Buy right once and you won't have to worry again" is too attractive a promise to give up.

But there are pieces that work across decades. I sell vintage ties from several different decades myself, and I have jackets from the 80s and 90s in my wardrobe that I wear regularly. Those pieces don't work because they're "timeless". They work because they are only lightly marked by the trends of their time: proportions that were never pushed to extremes and design choices that didn't chase the mainstream. Learning to spot those pieces is the real lesson. And when you find one that works for you, double down.

Basic form and proportion: where the decade really shows

To make this useful, you need to separate two things that almost everyone lumps together.

Basic form is what the piece is. An Oxford is an Oxford, a hundred years ago and today. A rep stripe is a rep stripe. Garza grossa is garza grossa. That basic form is stable, something you can hold on to. Real timelessness exists almost only at this level, in shoes and certain tie designs.

Proportion is how that form has been made up. Lapel width, buttoning point, gorge, rise, tie width. This is where the decade shows, and where a piece with an otherwise excellent basic form can still fail.

Two examples, both exactly the sort of thing I would normally spend money on. A tie in garza grossa, a coarsely woven tie fabric that has looked good for decades and will go on looking good. Great fabric, great design. But it is 6.5 centimetres wide, which makes it rubbish even if the garza grossa itself is fantastic. Or a jacket in camel Loro Piana cashmere, with wide lapels and the sort of material most people dream of. Then you see that the buttoning point sits below your balls. One proportion from the wrong era, and none of the lovely stuff around it can save the piece.

The untrained eye judges the basic form: rep stripe, therefore classic, therefore timeless, tick. And misses the proportion that changes the verdict. That is exactly why "Is it timeless?" is no help when you're buying.

Where to be careful: a hierarchy by category

How tricky a category is depends on how many things have to come together at once.

Shoes. The easiest case. The shape is stable; an Oxford remains an Oxford. Some shoes are more beautiful than others, but there are hardly any decade-specific traps.

Trousers. Surprisingly forgiving. High, medium or low rise, with or without pleats, straight, tapered or wide: almost all of it still works today. It is only slim and super-slim that make you look out of date.

Ties. There is more to them than width. Width can kill a tie, sure. But the shape of the blade, together with the outer fabric and interlining, also determines whether the finished knot looks thin or bulky. Extreme imbalance, very narrow at the top and heavy at the bottom, places a tie straight in the 80s.

Shirts. Fabric, pattern, collar and fit can all cause trouble. With the fit, aim for the middle: roomier than 2010, slimmer than the 90s.

Jackets. The trickiest category because everything has to work at once: silhouette, gorge, buttoning point, waist suppression. That makes sense. A jacket is the most complex thing in your wardrobe and the outermost layer, the one people see first. It is the least forgiving, and that is why it is the most common vintage purchase to get wrong.

Evidence from my wardrobe: what works and what doesn't

Two Burberrys jackets from the 90s. Wide lapels, a relatively low gorge and a low buttoning point, all details that would look "dated" in isolation. Yet the jackets work. The overall length is generous, the waist is nicely shaped and the gorge is a little lower than is usual today, but not extreme. None of the proportions was ever pushed too far, and together they balance each other out.

A Ralph Lauren jacket from the 80s, Made in USA. An unusually high gorge for its time, wide lapels, a medium buttoning point and, again, a well-shaped waist. It fits and it works. That, incidentally, is Flusser's point: Ralph Lauren designed classics rather than trends in the 80s, which is why the pieces have outlived their decade.

And what never works: older department store suits. Whatever the decade. They were always a bit trendy, but never truly great. They lack an anchor, a distinctive designer's hand in the cut, the design choice that will still turn heads in thirty years, for the right reasons. You can rule out older department store suits without a second look.

The lesson: Lean Into It works when a piece reflects a good, distinctive design choice. It doesn't work when that piece was merely following the mainstream of its time.

Look for the pieces with a faint decade code, then double down

Learning to read the code of a decade takes practice, not a rule of thumb. I can tell you to look at lapel width, buttoning point, gorge and rise. But is 6.5 centimetres too narrow or still just about right? Is that button too low or within reason? You only see it once you've handled a hundred jackets. I won't pretend I can teach you that in five lines.

What you can do from today: stop believing the "timeless" label. It is a sales pitch, not a quality a piece possesses. Instead, ask how strongly a piece is marked by the trends of its time. Anyone will recognise the strongly marked pieces at a glance in ten years. The ones with a fainter decade code, moderate proportions that reflect a distinctive design choice will keep working. When you find one of those and it works for you, buy more of it instead of the next trend experiment.

And if you don't want to put in the work, find someone who has already done the sorting: houses with a genuine house style, dealers who buy only what works for them. That isn't a weakness. It is a division of labour.

Or, to give Derek Guy the last word: “what's wrong babe, you hardly touched the classic, timeless clothing you thought would transform your life” (x.com).

For more conversations about menswear beyond the usual style-guide clichés, visit nielsklasing.com or find me on Instagram.