Timeless Men’s Fashion Is A Scam. Here’s What To Shoot For Instead

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For the past 13 years, I’ve told EG readers to strive for a timeless, classic style.

…to dress in outfits that won’t make you cringe when you see photos of yourself today in 10 or 20 years.

Here’s the problem with that advice: There is no such thing as a timeless men’s fashion.

So, how should guys dress, then?

Let’s get into it.

Why Timeless Men’s Fashion Isn’t Really a Thing

You’ve been told many times, even by me, here, on Effortless Gent, to focus on building your wardrobe with timeless basics… clothing that won’t go out of style, ever.

But if you look back on men’s fashion and clothing throughout recent history (e.g. the 1920s on), there isn’t one item that has stayed the exact same. Even your basic pair of jeans or a standard T-shirt has changed, albeit slightly, with fit, cut, and proportion.

Here’s the thing: This concept of “timeless basics” is a scam, a marketing gimmick that’s mostly made up in order to sell you something more expensive.

Every brand that sells you clothing on the premise that it’s a timeless basic that will never go out of fashion knows you’d justify paying more because of that reason. And that’s because, again, theoretically, you won’t have to replace it soon, if at all, because it’s “timeless”.

Buy It Because You Like It

There’s nothing wrong with buying a $100 T-shirt, or a $350 pair of jeans, so long as you are buying it because you just want to.

Any of the above reasons are perfectly fine to want to buy and wear something.

But if you’re buying something only because you were convinced it’s a timeless basic and therefore it’s worth spending more, solely because it will be relevant and in style “forever”… be prepared to be disappointed.

And here’s why:

The clothing itself may be timeless, the clothing combinations are timeless, but the details and proportions of both change over time.

Timeless men’s fashion (that isn’t so timeless after all)

So for example, a pair of denim jeans as we know them today has been around since the late 1800s (and the actual jean fabric, at least 100 years longer).

Denim style isn’t timeless…

But the jeans miners wore in the late 1800s are very different in style, cut, proportion, fabric makeup, even general purpose and cultural context, compared to the jeans today.

And what’s crazier: Even the way we wore our jeans 10-15 years ago is different than how we wear them today.

These scans (above) are from one of J.Crew’s Fall 2011 catalogs. Take note of the slim / skinny fits and low rise on the pants. Even the shirts and sweaters were slim.

Contrast that with the fall 2022 lookbook from J.Crew. Notice the higher rise and overall relaxed, slightly boxier fits. The fashion pendulum swings. It’s subtle, but there’s a difference.

Same goes for T-shirts, mid-layers, even some shoes that we were told were “timeless” 10 years ago are now looking a bit passé.

Even the classic suit has gone through (many) changes

The way suits are styled and designed today is very different from what they looked like in the 1920s, or the 1960s.

Take the Mad Men era, the late 50s into the early 70s.

While these slim silhouettes look relatively modern to us today, that’s only because we were re-introduced to them relatively recently, back in 2007 or 2008 when the show first aired.

The slim suit also took hold in the mid to late 2000s as part of the fashion pendulum swing, a reaction to the late 80s / late 90s structured, padded, voluminous suiting. And of course, towards the end of that swing, before we started heading in the other direction, “slim suits” were taken to a comical extreme.

Here are more J.Crew Fall 2011 catalog images (above). Notice the very slim suiting trousers with lowww rise and barely any drape, the skinny lapels on the jackets, the denim with suit jackets (not sport coats, but actual suit jackets).

While there’s nothing objectively wrong with these looks, if you were to style an outfit like this today, in 2022, it would look dated.

But if you look at suiting today, in 2022, we’re back to slouchier, more voluminous silhouettes. Take a look at the casual suiting examples in J.Crew’s 2022 lookbook (above). A fuller-cut leg, higher rise, more traditional width jacket lapels, full collars, etc. An overall more relaxed look.

The suit itself, or the sport coat / chino combo hasn’t changed… but the proportions, fits, and the way we wear them today has.

Trends change, So nothing is truly timeless

So, what have we learned?

So how does one avoid this? How do we avoid falling victim to trends, or spending money on clothes that will look dated in 6 months?

How To Achieve Timeless Men’s Style If There Is No Such Thing

Men’s fashion (like fashion, in general) is an ever-evolving, shape-shifting sorta thing. While it may not disappear completely, it will always be changing.

As long as you stay in “the middle” with at least part of your wardrobe, there are ways to appear “timeless”. This will also help you avoid being too trendy, or too boring or dated.

Here are three options.

Option 1: Buy clothes that are very “middle of the road”

Mid-rise, straight leg denim. White T-suits and sport coats.

Check out the denim photos above. On the left is the Levi 514 model. The other photos are from the 50s, possibly earlier.

Standard straight leg, mid-rise denim hasn’t changed that much. A mid-rise, straight leg version is pretty classic and probably won’t ever look out of date.

These classic pieces, with their decidedly “standard” styling, will more or less serve you well for 10-20 years, if not more.

There’s a chance you’ll look like you have no concept of current trends and silhouettes. Not that that’s “bad” or “wrong”. Just a decision you make, and depending on the story you want to tell with your clothing, might be the right move for you.

Option 2: Dress for the moment!

Dress for today, right now, and not worry about how relevant your wardrobe will be in 20 years, or 10 years, or even 1 year from now.

There’s a good chance that most of the stuff you own now, you won’t be wearing in a decade anyway, because as you dive deeper and deeper into developing your personal style, your tastes and preferences will change.

The way you prefer your jackets to drape, the slimness of your trousers, the looseness of your sport shirts… it all will change.

And if you’re actively experimenting with your style, figuring out what you like and what works / doesn’t work for you, there’s a good chance you’ll buy some duds that you won’t want to wear next year. And that’s totally fine, too. It’s all part of the process.

Option 3: Wear what you like! Mix and match old and new styles with abandon.

There’s a middle ground, another way to be eternally stylish… a way to avoid being a victim of ever-changing fashion trends, while also not succumbing to a 100% dated or boring, vanilla outfit.

Mix current, of-the-moment, trendy stuff you like, with basics you already own, or clothes you own that may be considered dated or passé.

For example, I might wear a tapered pair of jeans (which I prefer, even though denim styles are much wider right now) with an oversized crew neck sweatshirt (more aligned with the current style).

I have a relatively slim sport coat with narrow lapels I bought back in 2010, and I still love this jacket. I could wear it with a pair of straight leg chinos and a tucked-in T-shirt to bring it up to a more modern style overall.

There are many ways to mix your older, once-trendy stuff (what Gen Z may consider vintage) with current on-trend styles and fits.

Men’s Fashion Isn’t Timeless, but Your Personal Style Can Be

How clothing is styled and designed, and how we as a culture choose to wear our clothing, all changes over time. Nothing is truly timeless. But the moral of the story is: That’s totally fine.

Embrace a personal style that has elements of basics in traditional fits, mixed in with some current, on-trend items, and a few vintage, old-school items… and you can really come up with some great looks that exhibit a unique personal style that’s all your own.

Does that help?

If you have any questions or comments, DM me on Instagram! I’m also on Twitter and Effortless Gent’s Facebook page.

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