Why Classic Menswear Is In Danger Of Going Extinct

We’re all well aware that classic menswear has been on a downward trajectory ever since its apex in the middle of the twentieth century.

It was well on its way down by the time most of us were born. Outside of small surges in popularity throughout the decades of our lives (Armani and Wall Street in the 80s, the resurgence of James Bond in the 90s, Mad Men in the 2000s), we were never alive when classic menswear was the “norm”.

But for those of us who enjoy dressing in classic menswear, the styles (and the times they may conjure in the imagination) don’t feel all that distant. On the contrary, we always feel that classic menswear is primed for a bit of a comeback, given the cyclical nature of fashion, especially after the pandemic. 

Why, then, does a style of dressing that starting declining in the early 1960s feel approachable and “normal” to people our age who were mostly born in the 1980s and later?

That’s easy. Our grandparents.

Or, more specifically, our grandparents’ generation.

THEY were the ones who were right smack in the middle of the heyday of classic menswear. When we think of them, or we look at their pictures, they’re usually dressed more classically than most of the people we see walking the streets today.

Many of us knew our grandparents, or at least remember how they dressed. Or, more broadly, we knew how their generation dressed.

One’s grandparents’ generation isn’t that far removed from one’s own. Sure, it might seem like somewhat of a long time ago, but it’s not like it’s ancient history. After all, many of us remember our grandparents coming to Thanksgiving and Christmas. We remember getting cards on our birthdays. These people were part of our lives.

Even retailers and marketers tap into that familiarity by pitching products by saying they are as good quality as those our grandparent’s used. Or conversely, they say things like “not your grandfather’s” to make a product sound modern and improved.

Regardless of whether they position our grandparents’ style as good or bad, they are banking on the fact that it’s familiar and relatable to us.

Bottom line: the gap between us and our grandparents’ generation is not that wide. And the existence of that narrow gap is why WE can relate to those older styles.

So, why is classic menswear in danger of going extinct?

Because OUR KIDS will not be able to look to our grandparents’ generation with the same level of familiarity. That gap between our kids and their great-grandparents is much too wide.

And they certainly can’t look to their own grandparents (our parents). After all, our parents came of age in the counterculture 60s and 70s when tailoring was “for the Man, man!” That was the generation that brought us “casual Fridays” and influenced the rise of the sloppy, Silicone Valley styles which became such a flex for successful Gen-Xers and older Millennials.

I can even remember my dad telling me how much he hated having to cut his hair short when he was a Marine during Vietnam because it made him look like an un-cool member of the establishment.

Nope, our Boomer parents are more likely to look up to Mick Jagger and Jerry Garcia as style icons than Cary Grant. That’s certainly not the case with everyone from that generation, but taken as a whole, the Boomers definitely presided over the decline of classic menswear.

But is it really too much of a jump for our kids to look to our grandparents (their great-grandparents) for style inspiration, just like we do?

Yes, it is.

Let me give you a little perspective. Let’s think about the gap between us and OUR great-grandparents in order to see if we can relate to them and their style of dressing.

My paternal great-grandfather was born in Ireland in… wait for it…

1873!

That’s less than a decade after the Civil War ended!

He came to the United States around the turn of the century and my grandfather was born in 1914. That was the era of detachable-collar shirts and walking sticks, for goodness’ sake! It was the year World War One started!

I have no real connection to that era. I didn’t personally know my great-grandfather. He was born in the Victorian Era! He was getting married and having kids around the time of the invention of the zipper, the Titanic’s maiden voyage, and Einstein publishing his theory of general relativity. That was the age of Nikola Tesla, James Joyce, and Ty Cobb.

In terms of that time being relatable in any way, it’s so long ago it might as well be the Mesozoic!

That time is SO far in the distance that the styles would be costume if worn today.

And THAT’S how OUR kids’ generation is going to view the classic menswear of the 1930s-1950s! And that is why classic menswear in in danger of going extinct. There is simply too wide of a gap between our kids and the generation that lived during the peak of classic menswear.

The only hope is for US to keep classic menswear alive! WE need to set the example for how to dress so that it will (hopefully) rub off on our kids. We need to make it familiar and relatable to them, the same way our grandparents did for us.

How do we do that?

Well, you’re probably doing most of it already!

Wear classic menswear around the house so seeing it becomes commonplace for your kids. If you only bust it out on special occasions, it will seem costume-y and archaic, kind of like how white-tie looks to us now. Remember, you don’t have to be all gussied up in a coat and tie while at home. A sweater and chinos are enough.  Keep in mind that “classic menswear” encompasses so much more than just tailoring.

Make sure you enjoy it, though! Choose items that you can wear comfortably. Corduroy pants and a cardigan sweater (for winter) or a polo shirt and linen pants (for summer) are just as comfortable as gym shorts and a hoodie.

Lastly, it’s important to convey the benefits of dressing in classic menswear to your kids. This should be done as subtly as possible. You don’t want to beat them over the head with it because then their natural impulse will be to push back against it. Show them how GOOD they can feel when they dress well.

A great way to do this, I have found, is associating classic menswear with positive things. Days like Christmas or Mother’s Day are great chances to show your kids how to augment the “specialness” of the day just by what we wear.

But dressing well doesn’t have to be relegated to holidays. For example, make sure your kids see how you dress to take your wife out to dinner. They’ll not only notice how happy and excited you are, but they’ll hear the compliments your wife gives you.

All of this should make classic menswear seem familiar and fun to your kids.

Even if the lineage of classic menswear was somewhat disrupted by your parents’ generation, make sure you keep it alive so that it isn’t ancient history by the time your kids start caring about how they dress.