When My 72-Year-Old Aunt and 19-Year-Old Cousin Reached for the Same Sweater: What Fashion Generations Actually Share

So there I was last Christmas, nursing a slightly-too-strong eggnog and watching what might’ve been the most fascinating fashion moment of the year unfold in my parents’ living room. My aunt Martha – who’s 72 and has more style in her pinky than most fashion bloggers have in their entire Instagram feed – was eyeing this gorgeous cashmere cardigan my mom had tossed into the family gift exchange pile. At the exact same moment, my cousin Zoe (19, art student, basically lives in thrift stores) reached for the same sweater.

Their hands literally collided. I’m talking full rom-com moment, except instead of falling in love they both started that weird polite dance of “oh no you first” while clearly both wanting that oatmeal-colored cashmere masterpiece.

The thing is – and this is what made me nearly choke on my drink – they were already dressed almost identically. Zoe had on this oversized black cardigan that was basically the same silhouette, and Martha was wearing these perfectly tailored wide-leg pants that looked suspiciously similar to the vintage Levi’s Zoe had cuffed just so. When did a college sophomore and my great-aunt develop the same taste?

I’ve been thinking about this moment for months now, especially after I kept noticing the same weird generational crossover at work. Like, last month I was at this sample sale (because obviously I can’t afford retail), and I watched a woman who had to be pushing 70 and this kid who couldn’t have been more than 22 both make a beeline for the same rack of basic white button-downs. Not the trendy cropped ones or the oversized boyfriend styles – just classic, well-made white shirts that probably cost more than my rent.

“Quality over quantity,” the older woman said to no one in particular as she felt the fabric.

The younger woman nodded like she was in church. “Fast fashion is literally destroying the planet.”

Different reasoning, same conclusion. I stood there holding a polyester blazer I’d been considering (don’t judge, it was $12) and suddenly felt very called out.

This keeps happening everywhere I look. At Fashion Week – okay, I was only there for one show because my friend works in PR and got me a last-minute ticket – I ended up sitting between a legendary fashion editor who’s been in the game since before I was born and a TikTok creator with like a million followers. Both wearing straight-leg jeans, white shirts, trench coats, and I swear to god, New Balance sneakers. Just different colors.

The millennial influencer next to me was tottering around in these impossible platform boots, taking photos of her feet every five minutes. Meanwhile, the 22-year-old and the 68-year-old were having an animated conversation about arch support during the intermission. I felt like I was witnessing some sort of fashion alternate universe.

Here’s what I’ve figured out after months of accidentally conducting this bizarre sociological experiment: Gen Z and Boomers are basically shopping for the same things, just for completely different reasons. And honestly? They’re probably both right while the rest of us are out here making questionable decisions.

Take the whole quality thing. My neighbor Mrs. Chen – she’s got to be mid-seventies, still power-walks around the neighborhood every morning in these immaculate matching tracksuits – told me she’s been buying the same brand of cotton tees for literally decades. “Why would I waste money on garbage?” she asked when I mentioned seeing similar shirts at Target for a fraction of the price.

Three days later, I’m grabbing coffee and overhear this conversation between two Gen Z kids (okay, they’re probably my age, but when did I become the person who calls people “kids”?) about “investment pieces” and “cost per wear” and “ethical consumption.” One of them was wearing what looked like her grandfather’s perfectly maintained wool sweater, mended at the elbows with visible stitching that somehow made it look intentionally cool.

Same values, different vocabulary. Meanwhile, I’m over here with a closet full of stuff I bought because it was on sale, not because I actually needed it or even particularly liked it.

The shoe thing is maybe even more obvious. Both groups have completely abandoned the idea that you need to suffer for style. My aunt Martha has been wearing these gorgeous leather loafers for what seems like forever – they’re probably from the ’90s but they look timeless and comfortable. Zoe showed up to Christmas dinner in nearly identical loafers, just chunkier and with better tread.

“Don’t you want some heels?” my mom asked Zoe at one point, gesturing to her own sensible but definitely more formal pumps.

“Why would I torture myself?” both Martha and Zoe said at almost the same time. Then they looked at each other and started laughing.

I glanced down at my own feet – squeezed into some trendy ankle boots that were already making me want to amputate my toes three hours into the evening – and had what you might call a moment of clarity.

It’s not just shoes, either. Both groups are all about statement jewelry, just executed differently. Martha wears this incredible chunky gold necklace my uncle gave her years ago – it’s bold enough to make any outfit interesting but classic enough that it never looks dated. Zoe layers multiple necklaces with weird pendants (I think one was a tiny mushroom?) that somehow achieve the same effect of making a simple outfit look intentional and cool.

“One good piece is worth ten cheap ones,” Martha has told me multiple times, usually while I’m wearing some piece of costume jewelry that’s already turning my neck green.

Last week I heard almost the exact same sentiment from this editorial assistant at work who couldn’t be older than 23. She was wearing a single, substantial ring that probably cost more than my entire jewelry collection, but it made her simple black dress look expensive in a way my stack of fast-fashion rings never quite manages.

The color thing surprised me the most. After spending most of my twenties and thirties convinced that beige was a personality trait, I’m watching both ends of the age spectrum embrace actual color again. At this press event last month – don’t get too excited, it was for a brand I definitely can’t afford but the champagne was free – all the older editors and young influencers gravitated toward these gorgeous saturated blues and greens. The millennial editors? We were all clustered around the olive, camel, and black section like moths to a very boring flame.

My own closet looks like it was curated by someone who thinks oatmeal is a risky color choice. I’m not proud of this.

But maybe the weirdest convergence is how both groups approach trends themselves. They just… don’t? Not in the way the rest of us do, anyway. Both Boomers and Gen Z seem to have this immunity to the “must-have item of the season” marketing that gets me every single time.

“I know what works for me,” Martha said during our gift exchange, adjusting pants that were probably older than some of the people at the party but looked perfectly current.

“Trend cycles are just capitalism trying to make us feel bad about our clothes,” Zoe added, sounding more like a sociology professor than someone who presumably follows fashion TikTok.

They’re both approaching clothes from this place of confidence that I honestly envy. Boomers because they’ve lived through enough trend cycles to know what actually matters, Gen Z because they’ve grown up questioning the systems that tell them what they should want.

And then there’s me, refreshing sale websites at 2 AM because I heard wide-leg pants are “in” again and maybe if I buy the right pair I’ll finally look like I have my life together. Spoiler alert: this strategy has not worked yet.

I was complaining about this to my friend Sarah last week over drinks (well, she had drinks, I had a soda because I spent my drink budget on yet another sweater I didn’t need). “I wish I could shop like your mom,” I said. “She buys like three perfect things a year and calls it done.”

“Or like my little sister,” Sarah said. “She just wears whatever makes her happy and doesn’t stress about whether it’s ‘right’ or not.”

We sat there for a minute, both probably thinking about our closets full of clothes that seemed like good ideas at the time but don’t actually represent who we are or how we want to feel when we get dressed.

The thing is, both Martha and Zoe seem to have figured out something that I’m still struggling with: they dress for themselves. Not for trends, not for other people’s approval, not because some algorithm told them they needed a new jacket. They buy things they actually like, that fit their lives, that make them feel good when they put them on.

It’s such a simple concept that it’s almost revolutionary. At least it feels that way when you’re standing in your bedroom at 7 AM surrounded by clothes you spent good money on but don’t actually want to wear.

Maybe instead of trying to dress for my demographic or my career stage or whatever marketing category I supposedly fit into, I should be looking at what the youngest and oldest shoppers are doing right. They’ve found this sweet spot where comfort, quality, and personal expression meet, and they’re not apologizing for it.

The rest of us are still out here wearing uncomfortable shoes and buying things because they’re supposed to be flattering or professional or current, instead of just asking ourselves the most basic question: do I actually like this?

I’m not saying I’m ready to completely overhaul my approach to getting dressed. But watching my aunt Martha and cousin Zoe bond over cashmere and comfortable shoes while looking effortlessly put-together has me thinking that maybe there’s something to be learned from both ends of the fashion spectrum.

At minimum, I’m definitely investing in better shoes. My feet will thank me, and apparently, so will my style.