8 old-school fashion habits boomers nailed (and younger generations now copy)

Isabella Chase by Isabella Chase | July 15, 2025, 1:43 pm

There’s something about old-school fashion that just sticks, isn’t there? It’s fascinating how the styles that boomers wore effortlessly are now being mimicked by younger generations.

You see, when it comes to fashion, the baby boomers really got it right. They had this knack for creating looks that were both timeless and trendy.

Now, their iconic style is making a comeback and younger folks are taking notes. They’re realizing that these classic fashion habits are worth copying.

In this article, we’re taking a nostalgic trip down memory lane.

We’ll explore 8 old-school fashion habits that boomers nailed and which the style-conscious youth of today can’t help but replicate.

So, let’s dive into the world of fashion nostalgia and learn a thing or two from the boomers. Because honestly, they had some serious style game.

1) High-waisted everything

It’s no secret that the high-waisted trend is everywhere these days.

From jeans to skirts, swimsuits to shorts, the younger generation just can’t get enough of this flattering style.

But let’s give credit where it’s due. The boomers were the original pioneers of the high-waisted trend.

They knew how to rock a pair of high-waisted pants like no one else. It was a style that emphasized their curves and elongated their legs, all while keeping them comfortable.

Fast forward a few decades, and what do we see? A generation of millennials and Gen Zs who are embracing the high-waist trend with gusto.

So, if you’re wondering why your favorite pair of jeans sits just above your belly button, you have the boomers to thank for that.

They nailed this fashion habit long before it became cool again.

And honestly, we can’t help but emulate them. After all, they clearly knew what they were doing when it came to fashion.

2) The power of a good blazer

I remember rummaging through my grandpa’s closet as a kid and coming across this old-school navy blue blazer.

It had wide lapels, gold buttons, and a tailored fit that screamed classic boomer fashion.

Back then, I didn’t think much of it.

But as I got older and more fashion-conscious, I started to see the same style popping up in stores and online. Suddenly, the “old-man blazer”, as I used to call it, was everywhere.

Now, I own a similar blazer myself. It’s become a staple in my wardrobe – perfect for dressing up a casual outfit or adding an edge to corporate attire.

The boomers knew the power of a good blazer. They wore them to work, to parties, and even on casual outings. It was their go-to garment for instant sophistication.

Today’s younger generations are now following suit (pun intended).

A blazer can instantly transform any outfit into something chic and stylish. And we’ve got the boomers to thank for this timeless fashion trend.

3) The timeless charm of polka dots

Polka dots are a perennial favorite in the world of fashion, and we have boomers to thank for that.

Known for their playful charm, polka dots were a staple in the wardrobes of many boomers, adding a fun twist to their outfits.

Interestingly, the term “polka dot” came into being in the mid-19th century with the popularity of the polka dance, even though there’s no direct link between the two.

The pattern adopted the name from the dance craze during that era.

Fast forward to today, and you’ll find polka dots adorning everything from blouses to bathing suits, scarves to skirts.

Younger generations have embraced this trend, adding a dash of retro-cool to their wardrobes.

It’s a clear nod to boomer style and a testament to the enduring appeal of this simple yet impactful pattern.

4) Embracing the oversized look

Boomers were never shy about going big when it came to fashion.

From oversized sunglasses to wide-legged pants and roomy jackets, they embraced the oversized look with enthusiasm.

This fashion habit was all about comfort and style. It allowed them to create a unique silhouette and make a bold statement without sacrificing ease and freedom of movement.

Today, younger generations are drawing inspiration from this boomer trend. They’re borrowing elements of the oversized look, adding a modern twist to it, and making it their own.

Whether it’s an oversized denim jacket thrown over a cute summer dress or slouchy sweaters paired with skinny jeans, the influence of the boomers’ love for all things oversized is evident in contemporary fashion trends.

5) The sentiment of vintage jewelry

There’s something deeply sentimental about vintage jewelry. Those delicate pieces handed down from our grandmothers and grandfathers hold a special place in our hearts.

Boomers cherished these heirlooms, each piece carrying a story, a moment, an emotion.

That old-fashioned brooch, the charm bracelet, the string of pearls – they all held a significant meaning.

This appreciation for vintage jewelry wasn’t just about the aesthetics; it was about preserving memories and keeping the past alive.

Today, the younger generation is discovering the beauty of these timeless pieces.

They’re incorporating vintage jewelry into their style, not just for their unique charm but also for the stories they tell.

The trend is a tribute to the boomers, a nod to their style, and a heartfelt appreciation for their sentimental journey through life.

It’s about carrying forward their legacy in the most fashionable way possible.

6) The allure of the turtleneck

I admit, I used to find turtlenecks a bit intimidating. There was something about them that felt too formal, too sophisticated, maybe even a bit pretentious.

But as I grew older, I started seeing them in a different light.

Especially after noticing a black and white photograph of my mother from the ’70s, chicly dressed in a slim turtleneck sweater. She looked effortlessly elegant, and suddenly, I saw the allure.

Boomers knew how to wear turtlenecks with flair.

They paired them with everything from jeans to skirts, under suits or on their own. It was a versatile garment that added an air of refinement to any outfit.

Today, the turtleneck has made a big comeback among younger generations. It’s seen as a staple for any wardrobe – versatile, stylish, and oh-so-comfortable.

And I’ve learned to embrace it fully, finding my own way to style it, and loving the touch of sophistication it brings. Thank you, Mom!

7) The classic charm of a leather jacket

Boomers knew how to make a statement, and nothing said cool and confident quite like a leather jacket. They wore it with pride, adding an edge to their attire and a swagger to their steps.

From the rebellious biker look to the chic bomber style, leather jackets were a staple in boomer wardrobes. They were versatile, durable, and oozed a classic charm that was hard to resist.

Fast forward to today, and the leather jacket is as popular as ever.

Younger generations are embracing this trend wholeheartedly, pairing it with everything from dresses to jeans.

It’s a fashion habit that has stood the test of time, proving once again that boomers truly had their finger on the pulse of enduring style.

8) The enduring appeal of loafers

If there’s one shoe style that boomers nailed and that has proven to have an enduring appeal, it’s the loafer.

Practical, comfortable, and undeniably stylish, loafers were the footwear of choice for many boomers.

They wore them to work, to parties, and for casual outings.

The charm of loafers lies in their versatility – they can be dressed up or down and go well with almost anything in your wardrobe.

Today, younger generations are discovering the magic of this classic shoe. From traditional penny loafers to more modern designs, this shoe style has made a major comeback.

Loafers are a testament to the fact that boomer fashion trends aren’t just a nod to the past – they continue to influence contemporary styles in significant ways.

Final thoughts: The cyclical nature of fashion

The world of fashion, much like time itself, moves in a circular pattern. Styles of the past often resurface in the present, reinterpreted and reinvented for a new generation.

The allure of boomer fashion trends lies not only in their timeless appeal but also in the stories they tell.

Each trend is a snapshot of a bygone era – a reflection of the values, aspirations, and spirit of the boomers.

As younger generations look back, they’re not just borrowing elements of boomer style; they’re partaking in a rich legacy of self-expression and creativity.

So, whether it’s donning a pair of high-waisted jeans or slipping into a cozy turtleneck, remember that fashion is more than just clothes.

It’s a dialogue between generations, an echo of the past resonating in the present.

It’s about finding your personal style while honoring the trends that came before. After all, as French designer Yves Saint Laurent once said, “Fashions fade, style is eternal.”