7 things Boomers wear thinking they look put-together that actually look old-fashioned

Last Saturday at the farmers market, I watched a woman probably in her mid-60s walk past wearing a perfectly coordinated outfit. Matching bag, matching shoes, matching belt. Hair styled just so. Everything pressed and pleated and tucked within an inch of its life.

She clearly thought she looked polished and put-together. And technically, everything was neat and tidy. But the overall effect? Firmly stuck in 1987.

This isn't about age. I've seen plenty of Boomers who dress with incredible style, looking modern and intentional in their choices. But I've also noticed certain fashion habits that instantly date a look, making someone appear less put-together and more out of touch than they actually are.

After two decades in the corporate world followed by a complete lifestyle shift, I've paid a lot of attention to how we present ourselves and what messages we're unconsciously sending. And I can tell you that some of the things Boomers wear thinking they look polished actually have the opposite effect.

If you want to look current and intentional rather than stuck in time, it might be worth examining these seven habits.

1) Pleated front pants

I see this one all the time at the farmers market where I volunteer every Saturday. A well-meaning guy walks up to the produce stand wearing perfectly pressed khakis with deep pleats radiating from the waistband, and I can't help but think he's trapped in 1995.

Here's the thing about pleated pants. They were designed to provide extra room in the hip and thigh area, which made sense when everyone wore their pants at their natural waist. But fashion has moved on, and those pleats now create unnecessary bulk that adds visual weight exactly where most people don't want it.

Flat-front pants create a much cleaner, more modern silhouette. They're streamlined and work with your body rather than adding fabric where it's not needed. And yes, they're just as comfortable when you get the right fit.

If you love the comfort of your pleated pants, I get it. But consider trying a flat-front version in the same size. You might be surprised at how much more contemporary the look becomes with that one simple swap.

2) Matching everything to everything

My mother does this religiously. Her purse matches her shoes, which match her belt, which somehow also coordinate with her scarf. She thinks it looks polished and put-together. I think it looks like she's trying way too hard.

The overly coordinated look screams "I learned to dress in the 1980s and never updated my approach." Modern style is about intentional mixing, not perfect matching. It's about creating interest through contrast and complementary pieces rather than identical ones.

During my two decades in finance, I watched this play out in the office constantly. The women who looked most stylish were the ones who broke the matching rules. They'd pair brown shoes with a black bag, or mix metals in their jewelry. Meanwhile, those rigidly matching their accessories looked dated, even in professional settings.

These days, the goal is to coordinate without being matchy-matchy. Your accessories should work together in terms of formality level and general vibe, but they absolutely do not need to be the same color or material. In fact, they probably shouldn't be.

3) Vests over dress shirts

Unless you're completing a three-piece suit or working on a ranch, the vest-over-button-up look rarely works in today's world.

I'm talking about those sweater vests or quilted vests that get layered over collared shirts, creating a look that feels more "substitute teacher in 1992" than modern casual style. The problem is that vests add a layer of formality that clashes with contemporary casual aesthetics.

If you're going for warmth, a well-fitted cardigan or quarter-zip sweater does the job while looking infinitely more current. If you want to dress up a casual shirt, a blazer or jacket makes more sense.

The vest-over-shirt combination creates an awkward middle ground that's neither formal enough for business nor relaxed enough for casual settings. It's fashion limbo, and not in a good way.

4) Oversized, boxy blazers

Do you remember when blazers had shoulder pads that could double as football gear? When sleeves hung past your knuckles and the overall effect was "wearing your dad's jacket"?

Well, some Boomers never moved past that era.

When I left my finance career at 37, one of the things I was most excited about was ditching my collection of oversized blazers. These things had been "professional" staples, but they made me feel like I was playing dress-up in someone else's clothes. The fit was all wrong for a modern silhouette.

Today's blazers are tailored to actually fit the body. Sleeves should end at your wrist bone. The shoulder seam should sit at your actual shoulder. The overall cut should follow your natural shape rather than hiding it under excess fabric.

A well-fitted blazer can make you look polished and professional. An oversized one makes you look like you're drowning in fabric or borrowed someone else's clothes. The difference is dramatic and instantly noticeable.

5) Statement brooches on everything

A brooch can be a lovely accent piece. The keyword here is "accent," as in singular, as in not adorning every single lapel, collar, and cardigan you own.

I'm not saying brooches are inherently old-fashioned. Vintage brooches are actually having a bit of a moment in fashion-forward circles. But there's a difference between wearing a carefully chosen brooch as an intentional style statement and automatically pinning one to everything you wear because that's what you've always done.

The automatic brooch habit, especially when it's the same style over and over, can make an outfit feel dated and costume-like. It becomes a crutch rather than a choice.

If you love brooches, wear them. But wear them with intention. Choose pieces that feel special, and let them stand alone as a focal point rather than competing with three other brooches on the same outfit.

6) Athletic sneakers with dress clothes

Look, I'm a trail runner who logs 20 to 30 miles a week. I absolutely understand the appeal of comfortable footwear. My running shoes are some of my most prized possessions, and I'm all for prioritizing foot health over fashion suffering.

But there's a time and a place, and bright white athletic sneakers with dress pants or a skirt isn't it.

The problem isn't the sneakers themselves, it's the clash of aesthetics. Chunky, technical athletic shoes were designed for performance, not style. When paired with dressier clothes, they create a jarring disconnect that reads as "I didn't care enough to complete this outfit" or "I don't understand what works together."

Here's the solution: invest in some stylish comfortable shoes. Leather sneakers, loafers, ankle boots, or dressy flats can all provide comfort without the visual disconnect. Many brands now make shoes that look polished but feel like sneakers inside.

If you truly need athletic shoes for medical reasons, that's completely valid. But if you're just defaulting to them out of habit or convenience, consider exploring more cohesive options.

7) The aggressive tuck

Everything tucked in, all the time, no exceptions. That's the Boomer way, and honestly, it can really age a look.

I learned this during my career transition when I started paying attention to how different generations styled themselves. The younger professionals I met had a more relaxed approach to tucking. Sometimes yes, sometimes no, often a casual half-tuck that felt intentional but effortless.

The aggressive full tuck, especially when combined with a belt and those pleated pants we talked about earlier, creates a very rigid, dated silhouette. It's the sartorial equivalent of standing at attention.

Modern styling is more relaxed. An untucked button-up over jeans can look polished and intentional. A sweater worn untucked creates a longer, more flattering line. Even in professional settings, the full tuck isn't always necessary.

This doesn't mean never tuck anything. But it does mean being more intentional about when and how you tuck. A French tuck (front tucked, back untucked) can be incredibly flattering. Tucking just enough to show a belt buckle without the rigidity of a full tuck works well too.

The key is breaking free from the automatic tuck and making conscious choices about what works for each outfit and occasion.

Final thoughts

Here's what I want you to know. None of this is about following fashion rules for the sake of following rules. After spending nearly 20 years in a corporate environment where appearance mattered more than it should have, I learned that how we present ourselves genuinely affects how others perceive and treat us.

But more importantly, updating your style isn't about chasing youth or denying your age. It's about looking current and intentional rather than stuck in time. It's about making choices rather than following habits formed decades ago.

The people who look most put-together at any age are the ones who've evolved their style along with the times. They've kept what works, discarded what doesn't, and stayed curious about new approaches.

You don't have to completely overhaul your wardrobe or start following fashion influencers. Just take an honest look at these seven habits and ask yourself if they're serving you or aging you. Small updates can make a surprisingly big difference in how modern and intentional your style appears.

And if your mother still wants to match her purse to her shoes? Well, some battles aren't worth fighting. I learned that one through experience.