Timeless Style is a lie
It will keep you confused about how to look cool
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A couple months ago, an unexpected insight with profound implications occurred to me (Jonah): Harrington jackets look stupid now.
Specifically, the Harrington’s trademark feature, the collar. Left unfastened, it juts out with an inelegant, chode-style (sorry) chunkiness. Buttoned up, the effect of the doubled-over closure and those two closely spaced buttons is stuffy and not quite as goofy as the kitsch neck-belt on a Member’s Only jacket, but getting there. I posted about this to Twitter, using blunter language…
The implications here are profound because Harrington jackets are supposed to be a fully enshrined garment in the so-called “timeless” menswear pantheon. That is, they’ve been elevated in the modern clothes discourse to a sanctified realm putatively beyond trend cycles and, ipso facto, beyond stupidity.
To show that I wasn’t cherry picking, my tweet included screenshots of a Harrington collar from a totemic “timeless” menswear brand (Fred Perry) alongside two Harrington collars from an elite young Japanese line whose clothes I love (A. Presse, one of several great contemporary labels who make Harringtons that I am not f**king with). And to demonstrate my ironclad conviction, I included a picture of “Timeless Cool” paragon Steve McQueen rocking a Harrington back in the day and looking… much less cool than Steve McQueen when he rocked other things.
I’m not ready to say Harrington jackets look bad, full stop. I happily owned a tweed A.P.C. Harrington from roughly 2009-2013, and while I never loved it, it did not repulse me. What I’m saying is that Harringtons look conspicuously off right now, and you would look much better wearing something else. This is true of O.G. 1960s Baracuta G9 Harringtons, and it’s true of AW24 Auralee Harringtons.
If the Harrington is the timeless garment people tell us it is, however, then shouldn’t it always be hitting? And the next question you’ve got to ask is, “Are Harrington jackets in actuality not timeless — or is ‘timeless style’ itself a bogus concept?”
And the answer is clear:
Today I’ve got a Classic Spyplane Swag Semiotics Investigation for you into the lie of “Timeless Style” — a lie created by apparel-industry marketers, and perpetuated by their legions of alternately innocent and nefarious Handservants in order to hoodwink, confuse and frustrate you about What is Really Going On With Cool Clothes.
Let’s get into it —
Here’s an obvious but necessary first step in dismantling the “timeless” myth. We can consult pre-modern visual records of all manner of people who were saluted in their eras for putting that s**t on and whose clothes are, to today’s eyes, wack and/or illegible. Buckle-fastened silk culottes, velvet brocade tailcoats, that kind of thing. Once conventional and dope, now total nonstarters.
“Blackbird Spyplane,” you might be thinking, “you’re a brilliant thinker who deserves immense levels of respect, to the point that I’m probably making a mistake by interrupting you, but isn’t that pedantry? Cave dwellers wore animal pelts, so what? Human history contains vast epochs characterized by modes of presentation we now deem archaic. But if we narrow our focus to Living History, say, the last century or so, an aura of functional ‘timelessness’ clearly does attach to certain garments.”
I’m with you to a point. But I’d argue that the aura you’re talking about is far more chimerical and slippery than people tend to acknowledge.
To illustrate this, let’s set aside the relative novelty of the Harrington jacket and take a modern garment as putatively timeless and “core” as they come: the white button-front shirt. Consider all the variables that distinguish various button-fronts from each other, and the way these variables can work to date a piece. How big or small is the collar? Does it spread? Does it button down? Are its ends pointy or rounded? Is there a chest pocket? How big or small is it? Is the shirt cut to accentuate the waistline, or shaped more like a tent? How smooth or textured is the fabric? How high are the armholes? How thick is the cuff, and is it secured with a cufflink, with one button, or several? What are the buttons made from? How long is the shirt? Is the hem curved or flat? Also, we’re calling it a white shirt — are we talking white-white, or does it lean a little creamy? And on and on and on.
There is no precise set of answers to the above questions that, were you to answer them all “correctly,” add up to a Timeless White Shirt. Because even this humble, ubiquitous, classic garment is on some irreducible level a Fashion Object like any other, subject to myriad historical contingencies and shifting norms — and different eras favor garments that reflect different combinations of answers. The quest for the “perfect” t-shirt ends in the same exact ocean of variables, i.e., how cropped, how boxy, how long are the sleeves, how dropped are the shoulders, etc.
These differences are not only perceptible by hyper-plugged-in Clothes Watchers. Show up at a Proverbial Midwestern Office wearing a button-front shirt with lapels that so much as flirt with ‘70s-style enormity, and even Proverbial Brad from Accounting will roast your whole s**t, saying things like, “Hey Tony Montana, how’s life as a Miami cocaine dealer?” and “Where are the rest of the Bee Gees today?”
So we can celebrate pictures of James Baldwin, Miles Davis, and Paul Newman looking fantastic and “classically stylish” circa 1960 in Brooks Brothers button-downs all we want. But if you wanted to read as “classically stylish” circa 1987-1999 you did not want to wear a button-down that fit quite the same way those guys’ shirts did, thanks to the prep-revivers at the Gap and J. Crew, who commandeered the style and blew it up to a looser, more voluminous billow.
And if you wanted to look “classically stylish” from 2005-2013, you did not want to wear a button-down that fit the 1990s way nor the 1960s way, thanks to the influential prep-revivers at Band of Outsiders (peace to Spyfriend Scott Sternberg), who commandeered the style and tightened the armholes, added a rear box pleat and darting, and abbreviated the length for a neatly fitted “tiny boi” look echoed by other contemporaneous shirtmakers such as Gitman Bros., Gant Rugger, Engineered Garments, Steven Alan and Spyfriend Dana Lee.
And here’s the really disconcerting thing. It’s easy to look back at these styles now and readily perceive them as Obama-era “hashtag menswear”-coded. But in the moment, these shirts were sold — and they registered — as “timeless” !
Sure, you can lock into a pair of roomy-fit Carhartt double knees and a sized-up Barbour jacket for the rest of your days. But — depending on variables like fit & color, and depending on context such as How Recently Has Every Dude on Instagram Been Wearing Exactly That? — you will still look much less “with it” and much more “cooked” at certain points than others.
Just ask the painstakingly detail-oriented clothesmakers at venerated Japanese Americana-repro lines like The Real McCoys. Brands like this go to famously extreme lengths to replicate original MA1 flight-jacket specs down to the tensile strength of the nylon weave or whatever. And yet they still routinely modify the fit to comport more harmoniously with contemporary standards and tastes.
“Timelessness” changes, in other words, depending what time it is.
At this point you might say, “D*mn Jonah, another contemplative banger for the history books. But if Timelessness is a lie, what does that mean for stylistic consistency? Does the concept have no meaning?”
Great question. This brings us to the fundamental if fantastical appeal of the supposedly timeless garment: That you can give “fashion” a miss and achieve Gibraltar-like consistency, firm and un-eroding as the whiplash currents of trends swirl around your immovable edges.
When I think of Style Gibraltars — people synonymous with their consistency, but who stop short of literal uniforms — one that springs readily to mind is the fantastic British designer and Spyplane GOAT Margaret Howell.
Howell made her name in the late ‘70s by reworking casual menswear styles for women, eventually expanding to men’s clothes, too. She’s talked about taking inspiration early on from the way “real people” dress; from Katharine Hepburn, specifically “her lovely way of wearing men’s trousers;” from a formative childhood memory of her “dad’s raincoat hanging in the garage, faded and soft;” and so on.
When I think of an archetypal Howell outfit, I picture earth tones, natural fabrics, relaxed cuts, and designs that refer to early- and mid-20th-century British leisurewear and European workwear. In other words, I think of “timeless style” as we tend to talk about it currently.
Howell’s continuity of vision is demonstrated in the 4 pictures below, which span a gulf of 48 years:
Check her early designs from the late ‘70s ~ early ‘80s. Top left is the first jacket Howell ever made. It looks fantastic from a contemporary P.O.V., thanks to details that align pleasingly with where things are at now. Top right is Jane Birkin rocking a striped band-collar Howell shirt from the same era, tucked into pleated velvet or corduroy Howell trousers with a rope belt. It’s an unimpeachable look today, even if you mentally remove one of History’s Most Beautiful People from it. These older clothes fit 1-to-1 with my mental image of the “Timeless Margaret Howell Look,” as embodied by the outfits from FW24 and SS24 above bottom left and right.
But! What’s fascinating with Howell is that there’s a wealth of imagery in between that we can dig through to see what it actually looks like when a non-boring designer, averse to stagnation, practices consistency for ~50 years:
As the decades march on, even as Howell’s designs remain within the bounds of her consistently understated aesthetic, things start happening in the clothes that unavoidably look more or less dated now. I’m talking about an era-specific variation that’s palpable whether you just let your eyes wash over the fits or you linger on the details.
Some of this variation is down to things like hairstyles and accessories, and a lot of it is down to styling (e.g. the scoop-neck tee under the sportcoat on bruv rocking the skinny pants in Spring 2013). But many of the individual garments bespeak their eras in distinct ways, from color (the desaturated palette and predominance of blacks and grays in the ‘90s and early ‘00s), to fit (the “Sexy Drill Sergeant” energy in 1996), to other twists and modifications highly redolent of their times (the ultra-low-rise trousers with the gurkha-style cinches on ma in 2007).
And wow, look at the jacket the model is wearing in 2012 above bottom left. It’s exactly the same in theory as the first jacket Howell ever made! Except here the patch pockets are noticeably wider, the arms are shorter & more snug, and the overall length is cropped.
Now let’s look at some of Howell’s clothes over the past ~10 years:
The first thing I see here is that the color palette changes over, as the desaturated grays, black and blues of the previous collage give way to lovely reds and ochres, greens, oranges, yellows, pinks, warmth and deeper saturation.
The second, connected thing I see is that these are by & large garments you could rock today no problem. This is why Howell is one of the very best. The jacket from 2013 in picture A. could have come out last week. Ditto the 2017-18 fits in pictures B., C. and D. — even if the cropped pants, oversize peak lapels, and toggle closures don’t feel entirely “now.” By the time we get to picture H., from FW20, we are in Current Moment Mode — mamma mia, this whole look f**ks.
But change is brewing. In the final two fits above, pictures J. and K. from SS25, Howell is starting to mix in bluer and icier tones with the warmer browns. This, paired with the light-hued pants on king in photo K., feels especially fresh.
In other words, what we see when we look at 50 years of Howell is that consistency does not preclude change. To drive that point home, you can Google photos of Howell herself over the years and see that this is true not just of her designs but of her own outfits, too.
Some of the Howell looks in the above collages are not what’s popping circa 2024. There are decisions that doubtless made more sense at the time than they would now. Others reflect the kind of flexible, searching spirit that can lead to glory but also carries the risk of fit brickage. And that’s the ultimately inspiring thing. Consistency doesn’t and shouldn’t mean stasis.
Yes, developing consistency in your own style will significantly help to lessen mistake-making, but it can’t and shouldn’t obviate risk altogether. The person who buys into the oxymoronic lie of “timeless style” does so, I suspect, because they’re afraid of risk, and they hope to eliminate it entirely from their wardrobe. But that approach is misguided, boring, and at cross purposes with deep happiness and deep swag. If you cop a garment because it’s supposedly timeless you are A) engaging in bunk amateur history instead of putting that s**t on and B) setting yourself up for failure, anyway.
Strive for consistency, by all means (maybe you are a consistently protean zigger & zagger who never seems to settle in one place for long but is in fact guided by a complex undergirding set of affinities). Cop a garment because you think it’s dope, ingenious and beautiful. With time and wisdom, your hit rate will increase, but you will never zero out risk. That’s a beautiful thing, not a bummer, because risk is another word for LIFE!
P🌞E🌞A🌞C🌞E till next time — J & E
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The need for timelessness feels like the refusal to accept that the future will change and you will inevitably be on the outside looking in. It’s not under your control, but you desperately want it to be. Oh man life is scary and unpredictable but at least I’ve got the best timeless chinos in all 3 versatile colors from bonobos! I’m freed from the tyranny of worrying about that again.
This was so good. Coming off of a year of milestone birthday celebrations and preparing for a year of another, I’ve been looking a lot at old photos and noticed that when I get really excited about something I’m wearing it is because it feels true to me - not timeless, because I have changed and morphed across just about every possible axis, but more so feels *consistent* to my soul. Thanks for the giving words to my feelings.