Fashion is more than just an external display of personal style; it’s also a window into our mindset and how we adapt to changing trends.
Here at DM News, I’ve noticed there are certain habits that give away someone’s age in ways they might not even realize.
And while there’s nothing wrong with dressing in a way that feels comfortable, sometimes a few subtle shifts in style can help you seem more current—if that’s something you care about.
Let’s jump into seven fashion habits that (intentionally or not) may be sending out some seriously retro vibes.
1. Wearing socks with sandals everywhere
I’ll admit, there was a time I thought socks with sandals were the epitome of “dad style.” I remember once, back when I was freelancing in digital marketing, I took a quick coffee break in my neighborhood.
My neighbor—who’s a really nice guy in his mid-50s—greeted me wearing thick white socks and old Velcro sandals, looking perfectly at ease.
To him, it was about comfort and practicality. But for anyone under 40, that particular combination screams “throwback.”
It’s essentially saying, “I value comfort over contemporary fashion rules.” That’s okay if it’s intentional, but if you’d like to dodge that slightly “boomer” label, it might be worth ditching the socks—or swapping the sandals for comfortable sneakers.
2. Sticking to the same hairstyle for decades
I sometimes joke that my hair and I are in a lifelong partnership—one that occasionally needs refreshing to avoid going stale.
Sticking to the same hairstyle for decades, though, might inadvertently project the message that you’re not open to change. Now, I’m not suggesting everyone rush out and get a trendy cut every season, but experimenting with subtle updates can keep your look feeling current.
It’s similar to the concept that Gary Vaynerchuk once noted: “Your personal brand is your reputation. And your reputation in perpetuity is the foundation of your career.”
Granted, Gary was likely referring to social media presence and business branding, but I believe the principle applies to how we present ourselves too.
If your hairstyle seems stuck in the 80s, people may assume your mindset and skills are equally outdated—fair or not.
Plus, a fresh haircut or a slight tweak every now and again can go a long way in projecting openness and adaptability. It doesn’t have to be a dramatic change—maybe a different length, a new part, or a subtle texture. The key is showing you’re willing to keep evolving.
3. Tucking in every single shirt (no matter what)
I get it. There’s a certain neatness in tucking in your shirt, especially if you’re heading to a semi-formal event or a business meeting.
But if we’re talking about casual, everyday style, the perpetually tucked-in T-shirt can raise a few eyebrows.
I once observed this at a small local music festival. Nearly everyone was sporting relaxed, untucked tees or tank tops. Then came a small group of folks—definitely older—meticulously tucking plain T-shirts into jeans.
They stood out instantly, and not necessarily in a “cool vintage vibe” sort of way.
Tucking can indeed look great if done with intention (and if it complements your overall outfit). But if you’re doing it purely out of habit, it might be time to untuck and breathe a little.
There’s a reason so many younger people love the French tuck (where only the front is tucked, leaving the sides and back loose). It’s a middle ground between polished and relaxed.
4. Insisting on wearing only “comfort” brands (even at the expense of style)
Let’s talk about brand loyalty. Some folks discover a comfortable, familiar brand in their younger years—and then never branch out again.
You might see someone in the same style of sneakers they wore in the 70s or 80s, even though countless innovative (and more stylish) options are now available.
According to psychologists, our brains love predictability. Once we form a habit—like trusting a specific brand—we tend to stick with it, often without questioning if it still serves us well.
While comfort is crucial, clinging solely to the same old brand can come across as dated, especially if there have been notable design updates elsewhere.
As Simon Sinek famously said, “People don’t buy what you do; they buy why you do it.” While he was talking about business and consumer psychology, I like to apply the same logic to personal style.
If your fashion choices are driven by nostalgia or fear of trying new things, that might send a less flexible vibe. It can be fun (and surprisingly comfortable) to try alternative brands or styles every so often.
You might be pleasantly surprised by how fashion can meet function in new ways.
5. Matching everything too perfectly
Remember the days when color-coordinated outfits were the holy grail of dressing? Matching your shoes to your belt, your belt to your handbag, and sometimes even wearing identical shades from head to toe?
There’s a certain sense of order in matching everything precisely, but modern fashion tends to favor balance over exact color coding. Nowadays, mixing different tones or prints is often seen as cooler and more on-trend—provided it’s done thoughtfully.
Sometimes, a mismatch can look fresh. One of my close friends, who’s an interior designer, jokes that in her world, “perfection can seem stale.” The same principle applies to clothing.
If you see someone wearing a navy shirt, navy pants, and navy shoes day in and day out, it might come off as rigid. Allowing a bit of pattern or color play can instantly make an outfit seem more 2025 than 1975.
6. Always opting for practical over stylish shoes (in every situation)
I’ve mentioned this in a previous post, but footwear can be one of the biggest giveaways of generational style.
Practical shoes are essential—we all value supportive, comfortable footwear.
But if you’re constantly reaching for clunky, purely comfort-driven shoes regardless of the occasion, you might be sending a certain message.
Now, I’m no stranger to comfortable footwear. I live in California and love to hike, so my closet is home to plenty of durable boots and sneakers.
But if I’m going to a casual rooftop gathering or meeting up with friends at a trendy spot, I might switch it up to something sleek. Striking a balance between function and form is possible.
Tim Ferriss once said, “What we fear doing most is usually what we most need to do.” While he likely wasn’t talking about shoes, I believe there’s a parallel here.
Sometimes we avoid new styles out of fear—fear of discomfort, fear of standing out, or fear of making a fashion “mistake.” But stepping outside your comfort zone (quite literally, in this case) can lead to discovering shoes that look good and still respect your feet.
7. Wearing outdated jean cuts (and never exploring alternatives)
Last but not least, the jean conundrum. I’m sure you’ve seen it: high-waisted, baggy “mom” or “dad” jeans in a wash that hasn’t been popular since the 90s, or wide-leg jeans that bunch awkwardly over bulky sneakers.
Don’t get me wrong, certain vintage cuts have made a comeback, and I’m all for retro style if it feels intentional.
But wearing the same jean cut you picked up twenty years ago—without any update—often projects that you’re stuck in time. Denim, like any fashion staple, goes through cycles.
There have been skinny jeans, bootcut, flare, and now a resurgence of relaxed straight legs. Finding a fresh fit that suits your body type and lifestyle can dramatically modernize your look.
Putting it all together
None of us are immune to falling into fashion ruts—I’ve been there many times. It’s natural to rely on what’s comfortable and familiar, especially when life gets busy.
But if you’re hoping to avoid those subtle indicators that might date you more than you’d prefer, consider giving one (or all) of these habits a gentle refresh.
A modern haircut, a pair of shoes that balance comfort and style, or simply relaxing that tuck on a casual Friday can make a bigger difference than you might imagine.
And remember, fashion is a form of self-expression; it’s completely okay to evolve as you learn more about yourself and the world around you.
There’s no rule that says you can’t cling to a favorite brand or style if it truly makes you happy. However, if you’ve been on autopilot for a while, changing things up might reignite a spark of creativity or confidence in your daily life.
Here at DM News, we believe self-development isn’t just about what’s on the inside—it’s also about how we show up in the world.
So the next time you catch yourself reaching for socks to pair with your sandals or reflexively tucking in your T-shirt, pause and ask: Is this genuinely how I want to present myself today, or am I just following an old routine?
Sometimes, a simple tweak can speak volumes—no matter what generation you come from.
