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.

What suits looked like in the 20s and 30s

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.

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 A mid-rise, straight leg version is pretty classic and probably won’t ever look out of date.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

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