7 pieces of boomer fashion Gen Z is bringing back into style

I’ll admit it—if someone had told me in the early 2000s that shoulder pads, thick glasses, and loafers would be back in vogue by the time I hit my forties, I would’ve laughed mid-sip of my skinny vanilla latte.

But here we are.

Turns out, what once screamed “dad at a BBQ” or “mom heading to a PTA meeting” is now the pinnacle of cool—according to Gen Z, anyway.

This generation is diving into their parents’ closets (sometimes literally), plucking out pieces from the Boomer-era, and making them feel brand new. And the best part? They’re not just copying the past. They’re remixing it.

So what’s behind this surprising revival? I think part of it is rebellion. In a world saturated with fast fashion and disposable trends, Gen Z is pushing back with retro, recycled, and ironically timeless choices. They’re making conscious style decisions—and somewhere between the old Polaroids and vintage denim, they’ve found gold.

Let’s take a look at seven Boomer fashion staples that are making an unexpected (but very welcome) comeback.

1. Wide-leg trousers

Remember those high-waisted, pleated slacks our parents used to wear to work in the 70s and 80s?

Well, they’re no longer reserved for grainy office photos or real estate agent headshots. Gen Z has turned them into a wardrobe must-have.

I recently spotted a group of twenty-somethings walking through a local farmers’ market—every one of them in some version of these roomy, swishy trousers paired with cropped tops, oversized blazers, or vintage tees.

There’s a kind of effortless power in wide-leg pants. They say “I mean business,” but in a relaxed, comfortable, almost anti-corporate way. It’s a big departure from the skinny jean era of the 2010s, and honestly? It’s a lot kinder to circulation.

As noted by stylist Allison Bornstein, “The wide-leg pant brings a softness and sense of ease into a look—it’s structure without stiffness.”

2. Chunky orthopedic-style sneakers

These aren’t your sleek running shoes or minimalist Nikes. I’m talking about the thick-soled, support-focused sneakers that once lived in podiatry brochures and behind pharmacy counters.

And yet—Gen Z is rocking them like they’re runway gold.

The trend started with Balenciaga’s Triple S sneakers and spiraled into a full-blown revival of “ugly” dad shoes. Think New Balance 990s, Asics GELs, or anything with a bulbous sole and aggressive arch support.

What’s wild is how these shoes, once the butt of every dad-joke meme, are now considered peak street style. Maybe it’s the comfort. Maybe it’s the irony. Either way, they're no longer just for power-walkers at the mall.

3. Statement glasses

At some point, we all knew someone (usually a parent or teacher) who wore oversized glasses that seemed to engulf half their face. Back then, they were practical. Unapologetically nerdy. Maybe even a little awkward.

Fast forward to today and those exact frames—thick, square, and wire-rimmed—are everywhere on Instagram and TikTok.

There’s something oddly empowering about reclaiming what was once “unfashionable.” Gen Z isn’t just wearing these glasses to see better; they’re wearing them to be seen. The look says: “I’m smart, I’m bold, and I don’t need to shrink myself to fit in.”

As designer Jenna Lyons has said, “Eyewear has become part of the outfit—it’s not just functional, it’s fashion.” And Gen Z? They’ve taken that to heart.

4. Sweater vests

Raise your hand if you thought sweater vests were doomed to retirement homes and math teacher stereotypes. (Me too.)

But somewhere between quarantine-era boredom and the rise of cottagecore, sweater vests found their way back into the style spotlight. And Gen Z has embraced them with open arms—and open minds.

I’ve seen them layered over baby tees, styled with plaid skirts, or worn oversized with nothing underneath (a bold move, I’ll admit). It’s not the preppy, rule-following version Boomers wore. It’s got edge. Attitude.

There’s something a little rebellious about taking a symbol of conformity and twisting it into something playful and expressive. And isn’t that the best kind of fashion? When it challenges what we thought we knew?

5. High-rise jeans (the rigid kind)

For a while, we were living in a stretchy, low-rise denim haze. But Gen Z has dragged us back into the rigid world of Levi’s 501s, button flies, and no give whatsoever.

And somehow, it works.

There’s something grounding about this denim. It doesn’t mold to your body—it asks you to mold to it. That might sound uncomfortable, but many Gen Zers are leaning into the authenticity of it. These jeans feel real. They don’t pretend. They don’t flex. They just are.

It’s fashion as resilience.

I tried on a pair of vintage high-rise jeans recently (found buried in the back of my closet) and was surprised by how empowering it felt. Like I was standing taller. Walking slower. Owning space in a different way.

6. Headscarves and silk neck ties

There’s a certain elegance to this one.

Boomer women knew how to rock a good headscarf—whether tied around the chin, draped like Audrey Hepburn, or looped into a neat bow around the neck. It was part Hollywood glam, part suburban sophistication.

Gen Z has put their own spin on it. You’ll see these scarves used as tops, bags, belts—you name it. But when they do stick to the head or neck, it’s done with a wink. It’s vintage, yes—but with intention.

The scarf revival also taps into a deeper desire for slowness. These pieces aren’t fast fashion. They’re often thrifted or inherited. They have texture, history, and the kind of personality you can’t buy in bulk.

As one Gen Z stylist put it on a podcast I tuned into recently: “Scarves are like wearable stories. Each one feels like it belonged to someone who lived a little more slowly, and that’s the energy I want.”

7. Loafers

Last but definitely not least: the loafer.

Boomer fashion practically invented it—especially in the “office chic” category. Back then, loafers were polished, practical, and paired with everything from suits to skirts.

Now? Gen Z is turning them punk, preppy, and even subversive.

Loafers are being worn with visible socks, mini skirts, baggy jeans, and yes—no pants at all. The versatility is unmatched. You can dress them up or down. They straddle the line between “I’m going to work” and “I’m headed to band practice.”

I bought a pair recently on a whim (inspired by a teen on the subway, of all people), and they’ve become my go-to for days I want to feel grounded but still slightly defiant. They make noise when you walk. They announce you.

And sometimes, that’s exactly what we need.

Final thoughts

Fashion is never just about clothes.

It’s a reflection of what we value, what we resist, and how we want to show up in the world. Gen Z’s embrace of Boomer-era style isn’t just about nostalgia—it’s a form of storytelling. A slow-fashion rebellion. A nod to what came before with eyes wide open to what’s ahead.

And maybe that’s why I love this trend so much. It’s not about looking backwards—it’s about reaching back, pulling something forward, and giving it new life.

Kind of like self-development, really.

You don’t throw away your old habits or past selves. You sift through them, see what still fits, and wear it with pride.