9 outdated style choices boomers cling to that Gen Z quietly cringe at

I was at the farmers' market last Saturday when a woman around my mom's age complimented my outfit. Then she said something that stuck with me: "I could never pull that off. It's not really for my generation."

That comment got me thinking. Not about what she couldn't wear, but about the invisible rules we all carry about what's "appropriate" for our age. And how those rules often say more about fear than fashion.

Here's the thing: I'm not interested in generational warfare or making anyone feel bad about their style choices. But I am fascinated by how certain fashion habits persist long after they've stopped serving us, simply because they feel safe or familiar.

So let's talk about some style choices that boomers often hold onto, and why younger generations find them puzzling. 

1) Matching everything perfectly

You know the look. The navy pants with the navy blazer with the navy shoes and the navy bag. Everything coordinated down to the smallest detail, like getting dressed is a color-matching test.

Gen Z approaches fashion completely differently. They mix patterns, clash colors intentionally, and treat getting dressed like creative expression rather than a problem to solve correctly.

The boomer approach to matching often comes from a time when "put together" meant coordinated. But somewhere along the way, perfectly matched outfits started reading as overly cautious rather than polished.

There's something refreshing about grabbing what you actually like rather than what theoretically goes together. When I stopped trying to match everything during my transition out of corporate life, getting dressed became fun again instead of formulaic.

Fashion has always been about self-expression, but rigid matching rules can strip away personality in favor of playing it safe.

2) The dreaded jean shorts with white sneakers combo

This one shows up everywhere. Mid-length denim shorts, usually light wash, paired with pristine white athletic sneakers and often a tucked-in graphic tee or polo.

It's not that any individual piece is problematic. It's that this exact combination has become a uniform that signals a very specific demographic. Gen Z recognizes it instantly as the "I'm trying to be casual but following a script" look.

Younger generations play with proportions differently. Oversized shorts with chunky shoes. Fitted shorts with unexpected sneakers. Vintage athletic wear styled in ways that feel deliberately curated rather than accidentally matching.

The issue isn't the items themselves. It's that they're worn together so predictably that the outfit stops communicating anything about the person wearing it.

3) Avoiding trends entirely

I hear this one a lot: "I don't follow trends. I just wear what looks good."

But here's the uncomfortable truth. What you think "looks good" is often just the trends from whenever you decided to stop paying attention to fashion. You're not actually outside of trends. You're just frozen in the trends of 1995 or 2005 or whenever you checked out.

Gen Z doesn't follow every trend blindly, but they're willing to experiment. They understand that engaging with current fashion doesn't mean abandoning your personal style. It means staying curious and open rather than deciding you've figured it all out.

During my early finance days, I thought having a "uniform" meant I was above fashion. Really, I was just afraid to try anything that might not work. That's not confidence. That's rigidity disguised as practicality.

You don't have to wear everything trending on social media. But completely refusing to engage with contemporary style often comes from fear rather than preference.

4) The logo overload

Designer logos everywhere. Prominently displayed brand names on every visible surface. The handbag with the giant logo. The polo with the oversized emblem. The sunglasses where the brand name is practically the main feature.

This was peak status signaling in the 80s and 90s. But Gen Z finds it deeply cringe. They've grown up in a world where luxury is often about subtlety, where obvious logos can read as trying too hard or insecure about your status.

Younger generations prefer quiet luxury or thrifted pieces styled in unexpected ways. They're more impressed by creativity and authenticity than by visible price tags.

True style confidence doesn't need to announce itself quite so loudly.

5) Pleated khakis and tucked polos

This combination has become almost a caricature. Pleated khaki pants, usually in tan or stone, with a tucked-in polo shirt and a leather belt.

It's the unofficial uniform of a certain generation trying to look "nice casual." But to younger eyes, it reads as outdated and overly formal for situations that don't require it.

Gen Z has reimagined casual wear entirely. They've made sweatpants acceptable in contexts that would have been unthinkable twenty years ago, but they've also elevated casual pieces through interesting cuts, textures, and styling.

The pleated khaki look persists not because it's particularly flattering or comfortable, but because it feels safe. It's what you wear when you want to signal "respectable adult" without taking any risks.

But playing it that safe often means you disappear into a sea of identical outfits at every casual gathering.

6) Fleece vests over everything

The ubiquitous fleece vest, usually in navy or gray, worn over button-down shirts in situations that don't require additional warmth.

This became the uniform of a certain type of professional boomer, particularly in tech and finance. But it's become so associated with a specific demographic that it's lost any individual style appeal.

Gen Z approaches layering with more creativity. Oversized blazers over vintage tees. Unexpected jacket and pant combinations. Layers that actually add visual interest rather than just signaling "business casual."

The fleece vest has become fashion shorthand for "I've stopped thinking about what I wear." It's the sartorial equivalent of autopilot.

7) Cargo shorts with too many pockets

Cargo shorts show up on every "please stop wearing these" list, yet they persist. Multiple pockets everywhere, usually in khaki or olive, worn with the aforementioned white sneakers.

The defense is always practicality. "But I need the pockets!" Except most of those pockets remain empty most of the time. The real reason is that cargo shorts feel familiar and require zero thought.

Gen Z has found ways to be practical without sacrificing style. They've embraced utility wear in ways that feel intentional rather than default. Interesting cuts, unexpected fabrics, pieces that serve a function but also look considered.

The cargo short hangs on not because it's uniquely functional, but because changing would require admitting that comfort and familiarity aren't the same as style.

8) The aggressive side part

Hairstyles count as style choices, and the deeply carved side part has become generationally divisive. Boomers often maintain the same hairstyle they've had for decades, regardless of whether it still suits them or feels current.

Gen Z has embraced middle parts, curtain bangs, more relaxed approaches to hair that feel less rigidly structured. They're willing to change their hair as they change, seeing it as part of ongoing self-expression rather than a decision made once and maintained forever.

Clinging to the same hairstyle for decades often has more to do with fear of change than with the style actually working for you.

9) Avoiding anything that feels "too young"

This is the big one. The underlying belief that certain styles, colors, cuts, or trends are "not age-appropriate."

Gen Z doesn't buy into age-based fashion rules the same way. They see older people on social media rocking contemporary styles and celebrate it. What makes them cringe is when people their grandparents' age dress like they've given up on expressing themselves.

I've mentioned this book before, but Rudá Iandê's Laughing in the Face of Chaos: A Politically Incorrect Shamanic Guide for Modern Life completely shifted how I think about authenticity versus social expectations. He writes that "most of us don't even know who we truly are. We wear masks so often, mold ourselves so thoroughly to fit societal expectations, that our real selves become a distant memory."

That hit hard for me. I realized I'd been dressing according to unspoken "rules" about what was appropriate for my age and profession, not according to what actually felt like me. The book inspired me to question whether I was being authentic or just following a script I'd internalized decades ago.

The most cringe-worthy thing isn't wearing something "too young." It's refusing to evolve because you're afraid of breaking invisible rules that might not even matter.

Final thoughts

Look, wear what you want. Seriously.

But if you're wearing something purely out of habit, fear, or because you decided twenty years ago that this is what people your age should wear, maybe it's worth asking if those clothes still represent who you actually are.

Gen Z isn't cringing at boomers because they're older. They're cringing at the visible fear of being different, of standing out, of trying something new. They're cringing at the rigidity that says there's a "right" way to dress for your age.

The most stylish people of any generation are the ones who dress with intention and authenticity. They're not following rules. They're not frozen in time. They're engaging with fashion as a form of ongoing self-expression.