7 clothing items Boomers still wear that younger generations find completely outdated

I was sorting through some old boxes at my parents' house in Sacramento last month when I found my dad's collection of graphic tees from the '80s. Not the cool vintage kind that sell for $60 at Venice Beach thrift stores. The other kind.

My partner looked at one featuring a cartoon golfer and said, "Please tell me he doesn't still wear this."

He does.

Fashion is cyclical, sure. But some items seem to exist in a time warp, beloved by one generation and completely baffling to the next.

Here are seven clothing items that Boomers keep reaching for that make younger generations do a double take.

1) Cargo shorts with multiple pockets

You know the ones. Those khaki or olive-green shorts with enough pockets to carry a small camping trip's worth of supplies.

Boomers love them for their practicality. Where else can you store your phone, wallet, keys, sunglasses, and a small novel all at once?

Younger generations see them differently. To Millennials and Gen Z, cargo shorts represent the opposite of streamlined style. They're bulky, unflattering, and scream "I've given up on fashion."

The thing is, I get the appeal. When I'm hiking in Griffith Park, I want pockets too. But there's a difference between functional outdoor wear and wearing them to dinner.

My uncle showed up to a family barbecue last summer in cargo shorts so laden with stuff that he jingled when he walked. My nephew asked if he was carrying tools. He wasn't. It was just coins, a multi-tool, and three different types of gum.

2) Pleated front pants

Pleated pants were everywhere in the '80s and '90s. That extra fabric at the waistband was supposed to provide comfort and a more relaxed fit.

Today's fashion leans toward cleaner lines and flat fronts. Pleats add visual bulk and can make even slim people look wider than they are.

But Boomers often stick with them because they're comfortable and familiar. They bought a dozen pairs decades ago, and they still fit, so why change?

The disconnect is real though. I once watched a twenty-something sales clerk at a department store try to gently steer a Boomer customer away from pleated dress pants. The customer was genuinely confused about why it mattered.

"They're just pants," he said.

Technically true. But fashion is never just about function.

3) Oversized printed t-shirts with dated graphics

We're not talking about vintage band tees or ironic retro designs. We're talking about XL shirts featuring things like cartoon animals playing golf, beach scenes with palm trees and sunsets, or aggressive eagle graphics.

These shirts were bought at tourist shops, corporate events, or charity runs. They're comfortable. They're broken in. And Boomers see no reason to retire them.

Younger people tend to prefer fitted shirts with minimal graphics, if any. The oversized, baggy look went out (and then came back in a different way), but these particular shirts never got the memo.

My dad has a shirt from a 1997 company picnic that he still wears to mow the lawn. It features a hot dog wearing sunglasses. He thinks it's hilarious. My siblings and I have tried to hide it multiple times.

4) White athletic sneakers with jeans

This is a tricky one because white sneakers are actually back in style. The difference is in the execution.

Boomers typically wear chunky, heavily cushioned white athletic shoes designed purely for comfort and support. Think New Balance 608s or similar "dad shoes."

They pair these with medium-wash jeans and a tucked-in polo, creating a look that screams "I'm ready for my morning mall walk."

Younger generations have embraced minimalist white sneakers like Common Projects or Adidas Stan Smiths. Sleeker, simpler, and worn with a more intentional aesthetic.

The Boomer version isn't wrong. It's just a completely different vibe. One says "performance footwear," the other says "lifestyle choice."

5) Vests over everything

Fleece vests. Quilted vests. Fishing vests with a million pockets.

Boomers love a good vest. It adds a layer without the commitment of a full jacket. It's practical for transitional weather.

But younger people rarely reach for vests unless they're part of a very specific aesthetic, usually involving outdoor brands worn ironically or as genuine hiking gear.

The Boomer vest is different. It's often worn over a button-down shirt, sometimes even indoors. It's become a uniform of sorts, particularly among a certain demographic of suburban dads.

I see this every Thanksgiving at my parents' house. At least three uncles will show up in some variation of vest over collared shirt. They think they look put-together. My cousins think they look like they're about to ask if we've heard about their investment portfolio.

6) Jean shorts that hit above the knee

Not the trendy short-shorts that come and go. Not the carefully distressed denim.

We're talking about jean shorts cut several inches above the knee, often with a relaxed fit and maybe a cuff.

Boomers wear these all summer long. They're comfortable, they're cool in hot weather, and they can transition from yard work to casual outings.

Younger generations tend to prefer either longer shorts that hit at or just above the knee, or they go much shorter for a more deliberate style choice. The in-between length that Boomers favor feels awkward to them.

The fit matters too. Modern shorts tend to be more tapered. Boomer jean shorts often have a roomier, straighter cut that doesn't align with current silhouettes.

7) Logo polo shirts in bright colors

Golf brand logos. Cruise line logos. Corporate logos from jobs held twenty years ago.

Boomers accumulated these shirts over decades of golf outings, work events, and promotional giveaways. They're good quality. They've held up. Why not wear them?

Younger people generally prefer either no logo at all or very subtle branding. A giant polo player or company emblem across the chest feels dated and overly corporate.

The bright colors don't help. We're talking electric blue, bright yellow, vivid purple. Colors that were popular in the '90s and early 2000s but feel aggressive now compared to the muted, earth-tone palettes that dominate current fashion.

My dad has an entire drawer of these shirts. Each one tells a story about a conference he attended or a golf tournament he played in. To him, they're memories. To my nephew, they're "loud shirts that hurt to look at."

The bottom line

Fashion is personal, and comfort matters more than trends. If cargo shorts make you happy, wear cargo shorts.

But it's interesting to notice these generational divides. They reveal different priorities. Boomers often value comfort, practicality, and longevity. They bought quality items that lasted, and they see no reason to replace them.

Younger generations tend to prioritize aesthetics, current trends, and intentional style choices, even if it means replacing items more frequently.

Neither approach is right or wrong. They're just different.

And honestly? Give it twenty years. The stuff Millennials and Gen Z wear now will probably baffle whatever comes next. That's how this works.

My vintage vinyl collection looked ridiculous to my parents until records became cool again. Fashion is a circle. Everything comes back around eventually.

Even cargo shorts. Maybe.