Why Your Style Choices Are Adding 10 Years to Your Age (And How I Fixed Mine)

So this is going to sound harsh, but I watched my dad's older brother completely age himself out of relevance at a family gathering a couple years back, and it's stuck with me ever since. Uncle Mike was retiring from his law firm after like thirty years, giving this speech about finally being done with corporate life, you know? Seemed happy, looked healthy for a guy in his mid-sixties. But then I overheard my cousin's kid – she's maybe seven or eight – ask her mom why "the really old man" was talking so long. Her mom was mortified, tried to explain that Uncle Mike wasn't that old, but the kid seemed genuinely confused. "But he looks older than Grandpa," she whispered.

The thing is, Uncle Mike wasn't just aging naturally. Looking back at photos from that day, he was basically wearing a costume of what an old man should look like. These pleated pants pulled up to his chest, this massive blazer with shoulders from the Reagan era, shiny dress shoes that looked like they came from a medical supply catalog. It was like he'd decided that hitting sixty meant he needed to dress like he was eighty.

That moment really messed with me because I realized I'd been making some of these same mistakes. Not as extreme, but still. I'm twenty-five and already catching myself defaulting to "safe" choices that were probably aging me without me realizing it. Started paying attention to guys who looked older than they should versus guys who seemed to have their style figured out regardless of age.

Working in marketing, I see this constantly. Guys who are sharp and relevant in meetings but dress like they've given up on being current. Last month I was working with this consultant – let's call him Dave – who's maybe fifty-two but was getting treated like someone's dad who wandered into the wrong conference room. "People assume I don't understand digital strategy," he told me over coffee. "They literally explain basic concepts to me like I just learned what the internet is."

Dave wasn't dressing badly exactly. His clothes were clean, professional, probably cost decent money. But everything about his style was screaming "I stopped caring about how I look sometime around 2003." And it was killing his credibility in an industry that moves fast.

So what are these aging mistakes that even otherwise put-together guys make? I've been paying attention to this for a while now, talking to older guys I respect about what works and what doesn't, and there are some clear patterns.

First thing – and this one hit close to home because I was doing it too – is wearing stuff that's way too big. I used to think loose clothes looked more mature, more professional. Turns out I just looked like a kid playing dress-up in his dad's closet. But older guys do this too, often because they're self-conscious about their bodies changing.

This friend of my dad's, Greg, is a professor who's actually in pretty good shape for fifty-eight. But he was swimming in these massive dress shirts because he'd gained maybe fifteen pounds in his fifties and didn't want anything "clinging." Problem was, those oversized shirts made him look like he was shrinking inside his clothes. Classic old-man look, even though he's not that old and definitely not frail.

When he finally got shirts that actually fit his body – not tight, just properly sized – the difference was incredible. "I look like I lost twenty pounds," he said when we compared photos. He hadn't realized that trying to hide his slight weight gain was actually making him look heavier and older.

Second major thing I've noticed is guys getting stuck in whatever silhouette worked for them twenty years ago. Pleated pants, boxy suits, super-wide legs with fabric pooling everywhere. I get it – if something worked once, why change it? But silhouettes evolve gradually, and clinging to outdated cuts immediately dates you.

Dave, the consultant I mentioned, had been wearing the same style suit since the late '90s. Wide shoulders, pleated pants, the whole deal. Wasn't necessarily wrong at the time, but fashion had moved on without him. When I saw him in a more updated cut – natural shoulders, flat-front pants with a cleaner line – it was like seeing a different person. "No wonder people were treating me like I was obsolete," he said. "I looked like I was."

The third thing, and this one really gets me, is how guys start <a href="https://sartorialhim.com/the-80-20-rule-applied-to-mens-style-the-few-things-that-make-the-biggest-difference/">eliminating all color and texture</a> from their wardrobes as they get older. Like there's this unwritten rule that after fifty you can only wear navy, gray, and beige in the most boring fabrics possible. Creates this flat, lifeless look that screams "I've given up on being interesting."

My girlfriend's dad is in his early sixties but stays sharp partly because he refuses to fade into neutrals. Still wears rich burgundy sweaters, forest green chinos, textured fabrics that add visual interest. "I'm not trying to dress like I'm twenty-five," he told me once, "but I'm also not trying to disappear."

When Dave and I went shopping, he kept gravitating toward the same plain navy chinos he'd been wearing forever. I steered him toward similar pants in richer colors and more interesting textures. "They're still just pants," I pointed out, "but they don't look like you've surrendered to becoming invisible."

Fourth thing is neglecting the details, especially accessories. Guys default to the most generic, functional versions of everything – thick, basic belts, chunky orthopedic-looking shoes, outdated eyeglasses. Each choice seems minor, but together they create this aging effect that's hard to pinpoint but impossible to miss.

Greg had these massive wire-frame glasses from like 1998. "They work fine and they were expensive," he argued when I suggested updating them. But looking at photos of stylish older guys – architects, writers, creative directors – the difference was obvious. His outdated frames weren't just neutral, they were actively making him look older and out of touch.

Same with shoes. Those square-toed, super-shiny dress shoes with obvious rubber soles have become the universal uniform of "older guy who's stopped trying." Updating to something cleaner and more classic can subtract years without sacrificing comfort.

Fifth thing is developing this actively hostile relationship with anything modern. Can't tell you how many times I've heard older guys say stuff like "I don't get all this new fashion nonsense" or "Men dressed better in my day." This mindset doesn't just affect clothing choices – it creates this vibe of resistance to contemporary life that reads as elderly regardless of actual age.

Dave had this immediate negative reaction to anything he saw as "too trendy." After talking about it, I realized it wasn't really about the clothes. He was anxious about feeling outdated in his industry and was overcompensating by rejecting anything contemporary. Once he recognized this, he became more open to subtle updates that helped him look current without feeling fake.

Last thing is continuing to dress for your body from twenty years ago. Our proportions change as we age, and cuts that worked in your thirties might not flatter you in your fifties. My uncle's high-waisted pleated pants probably looked fine when he was carrying more weight in his chest and shoulders, but as his body changed, those same pants created a completely different and unflattering silhouette.

The solution isn't drastically changing your whole style, just honestly reassessing what works for your current body. Maybe adjusting rise heights, reconsidering jacket cuts, changing collar styles to better frame your face now versus ten years ago.

So what happened with Dave? He made thoughtful updates – nothing dramatic, just better fit, updated silhouettes, strategic color and texture. Three months later he emailed me: "For the first time in years, someone asked my opinion in a meeting without starting with 'as someone who's been in the industry a long time.'" People were responding to him as a current expert, not a legacy hire, just because he looked the part.

Greg updated his glasses, fixed his shirt fits, added more texture to his professor wardrobe. "Students started mentioning in evaluations that I seemed more 'engaged,'" he laughed. "Same material, same teaching style, but I guess I don't look stuck in the past anymore."

My uncle? After retirement, my aunt quietly helped him update his wardrobe using golf as an excuse. Better-fitting clothes didn't make him look younger in some artificial way – he's still got gray hair and wrinkles – but they stopped adding fictional decades to his appearance. He looks like himself, not a caricature.

The goal isn't chasing youth or pretending you're not aging. It's just making sure your style choices aren't artificially aging you beyond your actual years. Contrary to what guys fear, updating these things doesn't mean dressing "young" or inappropriate – it means dressing accurately for who you are now.

Because there's a huge difference between acknowledging your actual age and adding imaginary decades through poor choices. You can't control time, but you absolutely can control whether your clothes are working with you or against you. Sometimes the most age-appropriate thing you can do is not scream "I've completely given up" from across the room.