6 wardrobe staples that never went out of style (boomers just knew it first)

Last week, I was scrolling through Instagram when I saw my younger cousin reposting vintage photos of her grandmother from the 70s. The caption read: "Why did they dress so much better back then?" I laughed because I've been thinking the same thing lately.

My husband's grandmother lives in Santiago, and whenever we visit, I catch myself admiring her wardrobe. She has this effortless style that feels both polished and comfortable. Her closet is full of pieces she's kept for decades, and somehow they still look current.

What's funny is that Gen Z is obsessed with many of these same items. They're hunting them down in thrift stores and paying premium prices for them online. The fashion cycle has come full circle, and the things boomers never stopped wearing are suddenly everywhere again.

Here are six items that prove timeless style doesn't have an expiration date.

1. Straight-leg jeans that actually fit

Walk into any vintage shop in São Paulo and you'll see young people sorting through racks of old Levi's. They're looking for those classic straight-leg jeans that sit at the natural waist and fall cleanly to the ankle.

Boomers never abandoned this silhouette. While everyone else chased trends like ultra-low rise or extreme flares, they stuck with what worked. Now Gen Z is rediscovering why these jeans became a staple in the first place. They're flattering on most body types, they pair well with everything, and they don't go out of style every six months.

I switched to this fit about two years ago after cycling through every trendy denim style imaginable. The relief of finding jeans that just work is real. You can dress them up with a blazer or down with sneakers, and you never look like you're trying too hard.

The best part? Boomers already know all the good brands and where to find them. They've been wearing the same cuts for years while the rest of us were out here experimenting.

2. Simple gold jewelry worn every single day

My mother-in-law wears the same gold chain necklace and hoop earrings every day. She's had them since before Matias was born. When I asked her why she never switches them out, she looked at me like I'd asked why the sky is blue.

"Why would I change something that works?" she said.

Simple gold pieces have become the foundation of everyday style for younger generations. They're buying thin chains, small hoops, and delicate rings that they can layer and wear constantly.

This isn't about following trends. Boomers wear gold because it's classic, it goes with everything, and it lasts forever. You don't need to think about it in the morning. You put it on and forget about it until you take it off at night. That kind of ease is what makes a piece truly iconic.

3. Blazers that actually have structure

There's a blazer hanging in my closet that I bought three years ago at a consignment shop. The woman who sold it to me said it belonged to her mother, who wore it to work in the 80s. It has shoulder pads, a tailored waist, and buttons that close without pulling.

I've worn it more than any other jacket I own.

Boomers understand that a good blazer needs structure. It should hold its shape and make you look put together the moment you throw it on. Gen Z is figuring this out too, which is why vintage blazers are selling out everywhere. They're tired of the shapeless oversized versions that dominate fast fashion racks.

A structured blazer works because it does the heavy lifting for your outfit. You can wear it with jeans and look polished, or throw it over a dress and instantly feel more professional. My mother-in-law has five of them in different colors, and she rotates through them like clockwork.

The quality is different too. Older blazers were made to last, with real linings and proper tailoring. That's something you can't fake with cheaper modern versions.

4. White sneakers that are actually white

I used to think keeping white sneakers clean was a losing battle. Then I noticed that boomers somehow manage to keep theirs looking pristine for years.

They treat white sneakers like an investment. They clean them regularly, store them properly, and replace them when they start to look worn. White sneakers have become the most versatile footwear choice across generations because they pair with everything from suits to casual weekend wear.

Gen Z has embraced this same philosophy. Walk through any trendy neighborhood and you'll see young people in crisp white sneakers paired with everything from vintage jeans to tailored trousers. They've realized what boomers knew all along: a clean pair of white sneakers elevates any outfit without trying too hard.

I switched to wearing white sneakers almost exclusively after Emilia was born. Between walking her to the park and running errands, I needed something comfortable that still looked intentional. Now I keep a rotation going and clean them every week. It's easier than I thought, and the payoff is worth it.

5. Button-up shirts tucked into high-waisted bottoms

My husband's aunt showed me old photos of herself from the 70s wearing a crisp white shirt tucked into high-waisted trousers. She looked incredibly chic. When I told her Gen Z is obsessed with this exact look right now, she laughed.

"We never stopped wearing it," she said.

There's something undeniably polished about a tucked-in button-up. It creates a clean line, elongates your torso, and looks effortlessly put together. Boomers have been doing this for decades because it just works.

Gen Z is rediscovering this styling trick through vintage fashion and old film photos. They're pairing Oxford shirts with wide-leg jeans or tucking silk blouses into midi skirts. The silhouette is flattering and timeless, which is exactly why it keeps coming back.

I've started doing this more often myself. It takes the same amount of effort as leaving your shirt untucked, but the result looks so much more intentional. Plus, it solves the eternal problem of what to do with a shirt that's slightly too long.

6. Leather goods that get better with age

Last time we visited Santiago, my father-in-law showed me his leather bag. He bought it in 1985, and it still looks incredible. The leather has softened and developed a rich patina that you can't replicate with anything new.

Boomers invest in leather because they know it lasts. They buy quality belts, bags, and wallets that improve over time instead of falling apart after a season. Gen Z is now the fastest-growing segment of vintage luxury buyers, specifically seeking out well-made leather goods that have already stood the test of time.

There's something satisfying about using the same leather wallet for years and watching it develop character. You're not constantly replacing things or chasing new trends. You buy once, take care of it, and enjoy watching it age gracefully.

I recently bought a vintage leather tote from a consignment shop in Itaim Bibi. The woman who sold it said her mother carried it for twenty years. When I inspected it, I understood why. The craftsmanship is miles ahead of anything I could buy new at the same price point. Now I use it every day, and I plan to keep it for just as long.

Final thoughts

The fashion cycle is funny. We chase novelty for years, only to circle back to what actually works.

Boomers never stopped wearing these pieces because they're practical, flattering, and timeless. They don't need validation from trends or social media algorithms. They know what suits them, and they stick with it.

Gen Z is figuring out the same thing. They're learning that real style isn't about wearing what's new. It's about finding what works for your life and wearing it confidently. That's something every generation eventually discovers, usually after wasting time and money on things that don't last.

Maybe the real lesson here is that good style transcends age. When something is well made, flattering, and versatile, it doesn't matter who wore it first or when it was popular. It just works, and that's all that really matters.