6 things boomers still wear that Gen Z secretly finds iconic

Last week, I walked my husband to work like I do every morning. He wore his good leather loafers, the kind that look better with every scuff, and a tucked-in button-down shirt. Nothing flashy, just clean and put together.

A young guy waiting at the crosswalk glanced over and nodded at his shoes. "Nice kicks," he said. Matias thanked him, and we kept walking. But that small moment stayed with me.

We think of generational style as these separate universes. Boomers do their thing, Gen Z does theirs. But the reality is messier and more interesting. Some pieces transcend the timeline, and younger people are quietly noticing.

Here are six things boomers have been wearing forever that Gen Z is starting to appreciate, even if they won't always say it out loud.

1. Well-made leather shoes that actually last

My husband's loafers are almost ten years old. They've been resoled twice, polished more times than I can count, and they still look sharp. That durability catches people's attention now.

Gen Z grew up in the fast fashion era, where shoes fall apart after a season. When they see someone walking around in leather shoes that have held up for years, it registers. Quality like that feels almost rebellious in a throwaway culture.

There's also something about the look. Leather shoes age in a way sneakers don't. They develop character. The creases, the worn spots, the way they mold to your foot over time. Younger people are starting to see that as cool rather than old-fashioned.

It helps that vintage and secondhand shopping is huge right now. Thrift stores are full of well-made leather shoes from decades ago, and Gen Z is scooping them up. They might pair them with baggy jeans and a cropped tee, but they're wearing them.

2. Oversized blazers with a lived-in feel

Boomers have been wearing blazers since forever, usually in neutral colors and classic cuts. They throw them on over everything. Jeans, slacks, dresses. The blazer is the ultimate "I'm put together" piece.

Gen Z discovered oversized blazers a few years ago and ran with it. But here's the thing. The best ones are the vintage blazers that already have that worn-in, slightly boxy shape. The ones boomers have been pulling out of their closets for decades.

I see this all the time when I'm out with my friends. Some of them raid their parents' closets for blazers. Others hit up thrift stores looking for that specific relaxed fit. They want the blazer that looks like it's been places, not the stiff one fresh off the rack.

There's a practicality to it too. A good blazer pulls an outfit together without much effort. It works for meetings, dinners, or just running errands. Boomers figured that out a long time ago, and Gen Z is catching on.

3. Simple gold jewelry worn every single day

My mother-in-law wears the same thin gold chain every day. She's had it for over thirty years. She doesn't switch it out or layer it with other pieces. It's just always there, sitting at her collarbone.

That kind of consistency is coming back. Gen Z is moving away from the chunky, statement jewelry phase and leaning into delicate, everyday pieces. Gold hoops, simple chains, classic rings. The kind of jewelry you put on and forget about because it just becomes part of you.

The things we wear consistently become part of our identity. When you see someone wear the same piece of jewelry for years, it tells you something about them. It's not about trends. It's personal.

Boomers have been doing this forever. They pick a few pieces they love and wear them until they're part of their look. No overthinking, no constant rotation. Just the same gold studs or chain, day in and day out. Gen Z is starting to appreciate that simplicity.

4. High-waisted, straight-leg denim that fits properly

I remember when low-rise jeans were the only option. Everyone wore them, even if they didn't fit well. Then the pendulum swung back, and high-waisted denim made a comeback.

Boomers never really stopped wearing high-waisted jeans. They knew what worked. A pair of straight-leg jeans that sits at the natural waist is flattering on almost everyone. It creates a balanced silhouette without trying too hard.

Gen Z rediscovered this style and made it their own. The difference is, they're not just buying new high-waisted jeans. They're hunting for vintage Levi's from the '80s and '90s. The ones boomers wore back then and probably still have tucked away somewhere.

There's something about the fit and quality of older denim. It's thicker, more structured, and it breaks in beautifully. Modern jeans often feel too thin or stretch out too quickly. Vintage denim holds its shape and looks better with time.

5. Crisp white button-down shirts, no fuss

A white button-down is one of those pieces that never really goes out of style, but boomers have mastered the art of wearing it without making it feel stuffy.

They tuck it into jeans, roll up the sleeves, and go about their day. No overthinking, no styling tricks. Just a clean shirt that looks sharp.

Gen Z is bringing this back in a big way. I see younger people wearing oversized white button-downs with everything. Baggy jeans, miniskirts, layered under slip dresses. It's become a staple again, and the appeal is the same as it's always been. It's versatile, polished, and easy.

The white shirt is the ultimate democratic garment. It works across generations, genders, and personal styles. Boomers have known this forever, and Gen Z is realizing it now.

The trick is in the simplicity. No logos, no embellishments. Just a well-made white shirt that fits nicely. It's one of those pieces that makes you look more put together without trying too hard.

6. Analog watches that actually tell time

My husband wears a watch every day. Not a smartwatch, just a regular analog watch with a leather strap. It's quiet and functional, and it doesn't buzz or light up.

For a while, watches felt almost obsolete. Everyone checked their phones for the time. But Gen Z is bringing them back, and not just as fashion accessories. They're wearing them the way boomers always have, as simple, reliable tools.

There's something grounding about glancing at your wrist instead of pulling out your phone. You check the time and move on. You don't get sucked into notifications or texts. It's a small thing, but it makes a difference.

The watches Gen Z is drawn to are often vintage. They like the clean dials, the leather bands, the sense that the watch has a story. Boomers have been wearing watches like this for decades, and now younger people are seeing the appeal.

It's not about rejecting technology. It's about choosing when to engage with it. A watch gives you that option.

Final thoughts

Style isn't as generational as we think. Sure, every generation has its trends and preferences, but the best pieces stick around. They get passed down, rediscovered, and worn in new ways.

Boomers have been holding onto these classics for years, and Gen Z is starting to see why. Quality over quantity. Simplicity over excess. Pieces that last and look better with time.

Maybe it's not about what's cool or outdated. Maybe it's just about recognizing what works and making it your own.