9 ‘outdated’ boomer wardrobe staples Gen Z is secretly stealing

Farley Ledgerwood by Farley Ledgerwood | September 2, 2025, 7:50 am

Fashion operates on a thirty-year cycle, they say, but nobody warned us that Gen Z would raid their grandparents’ closets with such enthusiasm. Walk through any college campus today and you’ll spot more pearl necklaces than a 1960s country club luncheon.

This isn’t just nostalgia—it’s something more interesting. While millennials rebelled by wearing skinny jeans and minimalist everything, Gen Z’s rebellion looks suspiciously like acceptance. They’re embracing the very items that fashion magazines spent decades calling “aging” and “frumpy,” discovering what boomers knew all along: some things endure because they actually work.

The real twist? These aren’t thrift store finds. Gen Z is spending serious money to look like they’ve been shopping in their grandparents’ attic. Vintage fashion sales have exploded, with some ’70s blazers now costing more than their contemporary designer counterparts.

1. Blazers with actual shoulder pads

Remember when shoulder pads were fashion’s biggest punchline? Gen Z doesn’t. They’re buying structured blazers that would make Dynasty producers weep with joy. But here’s the thing—they’re wearing them over slip dresses and bike shorts, creating a power-meets-vulnerability aesthetic that feels entirely new.

The appeal isn’t hard to understand. In an era of work-from-home shapelessness, there’s something thrilling about clothes that hold their own shape. These blazers create instant presence, something Gen Z craves in their transition from Zoom squares to real-world spaces. Your grandmother’s boardroom armor is now their confidence costume.

2. Pleated trousers that don’t apologize

For years, fashion told us pleats added visual weight. Gen Z responded by buying every pair of pleated wool trousers they could find. They’re not wrong—these pants do something magical that flat-front everything can’t: they move beautifully.

The wide-leg pleated trouser trend isn’t about hiding anything. It’s about taking up space, about clothes that announce themselves when you walk into a room. Paired with cropped tops and chunky sneakers, these trousers become less “corporate dad” and more “I own my decisions.”

3. Cardigans (yes, actual button-up cardigans)

Mr. Rogers would be thrilled. The cardigan—that symbol of tepid domesticity—has become Gen Z’s favorite layering piece. But they’re not wearing them with sensible slacks. They’re throwing them over slip dresses, wearing them as tops with nothing underneath, turning comfort into statement.

The genius is in the subversion. A cardigan worn traditionally signals conformity. A cardigan worn with latex pants or over a corset? That’s fashion anarchy disguised as grandparent approval.

4. Pearl necklaces without irony

Pearls were supposed to be finished—too traditional, too restrictive, too “ladies who lunch.” Gen Z didn’t get the memo. They’re layering pearls with chain necklaces, wearing them with graphic tees, treating them like the ultimate gender-neutral accessory.

The transformation is remarkable. What once signaled conservative propriety now suggests confident playfulness. When Harry Styles wears pearls to the Met Gala, he’s not channeling Barbara Bush—he’s rewriting the rules about who gets to wear what.

5. Loafers that mean business

The loafer revival might be Gen Z’s most practical theft. While millennials suffered through a decade of uncomfortable pointed-toe everything, Gen Z went straight for the classic penny loafer. Comfort, it turns out, isn’t just for boomers anymore.

But watch how they style them: with athletic socks pulled high, with micro-minis, with oversized suits. The loafer becomes a wink—I could be heading to a board meeting or a rave, and honestly, both require comfortable shoes.

6. Quilted jackets that actually insulate

The quilted jacket—Barbour-style, barn-coat practical—has become downtown cool. These aren’t fashion versions either; Gen Z wants the real thing, the kind with actual down filling and pockets that hold things.

There’s something deeply satisfying about watching twenty-somethings discover that warmth is fashionable. After years of suffering through winter in insufficient coats for the sake of silhouette, they’ve realized what their grandparents knew: being warm is its own kind of luxury.

7. Silk scarves for your neck (and head, and bag)

The silk scarf seemed destined for fashion exile—too fussy, too “lady at the country club.” Yet here’s Gen Z, tying them around their necks, wearing them as headbands, using them as impromptu tops.

The appeal makes sense when you consider Gen Z’s relationship with gender fluidity. A silk scarf is inherently non-binary—it’s whatever you make it. That flexibility, that refusal to be just one thing, speaks to a generation that refuses to be categorized.

8. Vests as actual outerwear

The sweater vest walked so the formal vest could run. Gen Z has discovered that vests—wool, tweed, even pinstriped—make perfect standalone tops. No shirt required, though sometimes they’ll add one for fun.

This isn’t prep school cosplay. It’s about finding the sweet spot between formal and casual, between covered and exposed. A vest says you thought about getting dressed but didn’t overthink it—peak Gen Z energy.

9. Oxford shirts buttoned all the way up

The buttoned-to-the-top Oxford shirt, no tie, is having a moment. What boomers wore to look professional, Gen Z wears to look interesting. It’s simultaneously uptight and rebellious, conservative and queer-coded.

The buttoned-up look works because it’s so intentional. In an era of strategic dishevelment, choosing to button every button is almost punk. It suggests control, precision, a person who makes choices rather than following defaults.

Final thoughts

What looks like fashion recycling is actually something more profound—Gen Z’s recognition that authenticity doesn’t require constant novelty. They’re not wearing these pieces ironically or even nostalgically. They’re wearing them because they work, because quality endures, because sometimes your grandmother’s closet contains better clothes than anything fast fashion can produce.

The real revelation isn’t that fashion is cyclical—we knew that. It’s that Gen Z has figured out what boomers learned through experience: certain pieces persist because they solve real problems. A good blazer creates authority. A silk scarf adds elegance. Comfortable shoes let you focus on where you’re going rather than how much your feet hurt.

Maybe the greatest theft isn’t the clothes themselves but the attitude: buy quality, wear what works, and don’t apologize for practicality. In trying to rebel against fashion rules, Gen Z accidentally discovered the ultimate boomer wisdom—that true style means wearing what you want, trends be damned. The revolution, it turns out, looks a lot like coming home.