For the past 7.5 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, classic style.

So, how should guys dress, then?

Check out the video and read more below it.

While classic pieces do exist (think suits, denim, T-shirts, etc.), the way they’re designed and the way we wear them have changed over the decades.

Case in point:

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

classic timeless style doesn't exist

What suits looked like in the 20s and 30s

classic timeless style doesn't exist

What suits looked like in the 50s and 60s

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.

“So how am I supposed to dress, then?!”

You have two options.

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

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

classic timeless style doesn't exist

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

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 A mid-rise, straight leg version is pretty classic and probably won’t ever look out of date.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.

You’ll also 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 10 or 20 years.

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.

You want to love how you dress right now, today

If you love how you dress today, you’ll feel more confident, and that confidence will show through, and people will notice.

You’ll feel better, you’ll look better, everything will be better.

I explain my thought process in today’s video. (By the way, make sure to subscribe to Effortless Gent on Youtube!)


Learn a few shortcuts to dressing well

Enter your first name and email, and I'll send you a free eGuide with quick and easy tips you can use today.

4 Responses

  1. Jack on

    Hey Barron,

    This is an interesting topic. It’s nice to see somebody at least questioning the mantra that men can get away with just buying classic pieces.

    My own opinion is to strike a balance between timeless and current. While you might not be able to buy timeless clothes, you can very easily buy clothes that will be fashionable for 5-years or a decade. Let’s take slim jeans. Men have been wearing slim – tight pants since the 70’s and they are still worn today. But what’s changed? Well, most people don’t wear leather pants anymore. They also don’t wear skin-tight.

    So, what can we learn from that? Take trends with a grain of salt. Them them influence your wardrobe rather than control it. Leather pants were something new, it wasn’t classic and it quickly faded away. Likewise, skin-tight was primarily a fad, that cut was new but quickly disappeared.

    Most trends are just trends. Whilst I do agree that timeless is pretty much impossible, buying clothes that last a decade is very possible.

    You don’t quite need to go middle of the road, you should just avoid going to the far side of following trends – buy the slimmer, lighter blue jeans. Like you said, enjoy now and feel good now. But maybe resist the white skin-tights.

    Jeans will be cool for the next 20-years, I’m pretty darn sure about that. Right now, slimmer jeans are still very fashionable and they likely will be for the next 5-years. So I don’t feel any risk in buying them. But when I see people wearing 3/4 grey checked suit trousers, I’m fairly confident that within 5-years that won’t be fashionable.

    Hopefully that made some sense.. it’s early!

    • Barron on

      Well said! Striking that balance is key. A good example is the slim-is-in, wide-is-in yo yo when it comes to men’s pants (see here:

      The trend of wider pants are coming back after a decade+ of skinny. Am I going to try it out? Right now, I think not, but who knows how I’ll feel in 1-2 years. Overall, I’m confident in saying a relatively straight or slim (though not skin tight), tapered pair will look relevant no matter what.

      And like you said, it’s ok to try new things as long as they’re an accompaniment, not a cornerstone, of your wardrobe.

      • Red Knight 2014 on

        TBH, I think men’s trousers have been far too tight for years and I’ve refused to wear them in narrow/taper leg let alone drainpipe/skinny. I’m glad if it is the case that wide trousers are making a comeback, because otherwise I was going to resort to tailoring.

  2. Red Knight 2014 on

    Fashion isn’t really for men – it’s fickle, ridiculous and is more to do with being dramatic than actually making men look good. What we need are proper standards regarding fit and such needs to suit a wide variety of tastes, physiques, functions and styles. Getting the fit right isn’t about taking out all the extra fabric, but is much more about getting the amount of extra fabric right – extra fabric that I call styling fabric. For example, fabric is only excess when it extends beyond the styling limit (1″ to 4″ of folded fabric in a shirts over the body measurements (chest and waist) divided by two).