The most unintentionally brutal style assessment I’ve ever witnessed happened at my uncle Bill’s retirement party five years ago. Uncle Bill—a good-natured corporate lawyer with a self-deprecating sense of humor—had just given a speech about looking forward to golf, grandkids, and never wearing a tie again. As the crowd dispersed toward the bar, I overheard his colleague’s eight-year-old daughter ask her mom, “Is Uncle Bill a hundred years old?” Her mom, mortified, whispered, “No, honey, he’s only 65.” The little girl looked genuinely confused. “But he looks like Grandpa, and Grandpa is super old.”
Here’s the thing: Uncle Bill wasn’t just aging naturally. He was aging himself through a combination of style choices that had calcified sometime around 1987. The pleated khakis hiked up almost to his armpits, the oversized blazer with giant shoulder pads, the shiny square-toed loafers… it was like he was deliberately trying to look like a caricature of an elderly man, despite being physically fit and mentally sharp.
I’m not sharing this to mock my uncle. I’m sharing it because that moment crystallized something I’ve observed repeatedly in my work: certain style choices can unintentionally add years, even decades, to your appearance. And the most insidious part? These aging style mistakes often masquerade as “playing it safe” or “dressing appropriately.”
Last month, I worked with a client named Michael, a 52-year-old tech executive who came to me because he felt invisible in his industry. “I walk into meetings and people assume I’m someone’s dad who got lost,” he told me. Michael wasn’t dressing poorly in any conventional sense—his clothes were clean, appropriate, and relatively expensive. But his style choices were aging him well beyond his years, undermining his actual energy, relevance, and capabilities.
So what are these aging mistakes that even otherwise well-dressed men make? And more importantly, what are the simple alternatives that can subtract years from your appearance without veering into trying-too-hard territory? After working with hundreds of clients across different age brackets, I’ve identified the most common culprits.
The first and most visually impactful mistake is improper fit—specifically, wearing clothes that are too large. This one transcends age brackets but becomes particularly aging after 40. The misconception seems to be that looser clothes hide physical imperfections, when in reality, they create a shapeless silhouette that reads as elderly.
My client Gregory, a fit 58-year-old professor, was wearing dress shirts two sizes too large because he’d gained a bit of weight in his fifties and was self-conscious about it. “I don’t want anything clinging to my midsection,” he explained. The problem was that his oversized shirts created the visual impression of a man slowly disappearing inside his clothes—a classic signifier of advanced age.
The fix wasn’t skin-tight shirts that showcased every contour. It was simply proper fit: shirts that skimmed his body with about an inch of fabric to spare. When he saw photos of himself before and after, the difference was startling. “I look like I lost twenty pounds and five years,” he marveled. He hadn’t realized that his attempt to hide his midsection was actually making him look older and heavier.
The second major mistake is sticking to an outdated silhouette, particularly when it comes to suits and trousers. Nothing screams “I haven’t updated my wardrobe since the Clinton administration” like pleated pants with a baggy cut and excess fabric pooling around the ankles. Similarly, suits with exaggerated shoulders and a boxy cut instantly add years to your appearance.
This doesn’t mean you need to embrace every trend that walks down the runway. It means understanding that silhouettes evolve gradually, and staying current doesn’t require abandoning good taste or classic style. For pants, a straight or slightly tapered leg with little to no break at the ankle looks timeless and clean. For suits, a natural shoulder line and a gently shaped waist creates a silhouette that’s neither trendy nor outdated.
Michael, my tech executive client, had been wearing the same suit silhouette for twenty years—boxy, with wide shoulders and pleated pants. When I put him in a suit with a more natural shoulder and flat-front trousers with a cleaner line, the transformation was immediate. “I didn’t realize how dated my other suits looked until I saw this,” he said. “No wonder people were treating me like I was obsolete.”
The third aging mistake—and I see this constantly—is reflexively dressing “more conservatively” with age, specifically by eliminating color and texture from your wardrobe. There seems to be an unwritten rule that after 50, men should transition to a wardrobe of exclusively navy, gray, and beige items in smooth, solid fabrics. This creates a flat, one-dimensional look that reads as elderly even if the individual items are perfectly fine.
My friend Robert, a stylish guy in his sixties, calls this “the gradual fade to invisibility” and deliberately counters it by incorporating rich textures and strategic pops of color. “I’m not trying to dress like my grandson,” he says, “but I’m not going to dress like I’m attending a funeral every day either.”
The fix here isn’t wearing neon or dressing like a fashion influencer. It’s simply maintaining some visual dimension in your wardrobe through texture (tweed, corduroy, chambray, knits) and judicious color (rich burgundy, forest green, deep purple, burnt orange). These elements add visual interest and energy to your appearance without looking like you’re trying to recapture your youth.
When I took Michael shopping, he gravitated toward the same navy blue smooth cotton chinos he’d been wearing for years. I gently redirected him to a pair in a slightly more textured fabric and a richer, more saturated shade of blue. “They’re still blue pants,” I pointed out, “but they don’t read as ‘I’ve given up.'”
The fourth mistake is neglecting the details, particularly when it comes to accessories. As men age, they often default to the most generic, functional versions of necessary accessories—the widest, most basic leather belt; the chunkiest, most orthopedic-looking shoes; the least distinct eyeglasses. Each of these choices might seem inconsequential in isolation, but together they create a cumulative aging effect.
Gregory, my professor client, was wearing massive square wire-frame glasses that had been stylish briefly in the late ’90s. “They were expensive and they work fine,” he reasoned when I suggested an update. I pulled up photos of several distinguished older men—architects, writers, film directors—who wore distinctive but classic frames that complemented their face shape. The contrast was striking. His outdated frames weren’t just neutral; they were actively aging him.
Similarly, square-toed, overly shiny dress shoes with visible rubber soles have become a universal signifier of “older man who doesn’t care anymore.” Updating to a simpler, more classic shape with a less plasticky finish can subtract years from your appearance while still providing comfort.
The fifth mistake is perhaps the most subtle but insidious: developing an actively antagonistic relationship with modern style. I can’t count how many times I’ve heard variations of “I don’t get all this new stuff” or “Men’s style was better in my day” from clients. This mindset doesn’t just affect clothing choices; it creates a perceptible resistance to contemporary life that reads as elderly regardless of actual age.
This doesn’t mean blindly embracing every trend. It means maintaining a sense of curiosity and discernment rather than reflexive rejection. My most stylish older clients aren’t the ones who dress like 25-year-olds; they’re the ones who periodically reassess their choices and thoughtfully incorporate elements that feel relevant to their current life.
When working with Michael, I noticed his immediate negative reaction to anything he perceived as “too modern.” After some conversation, it became clear this wasn’t actually about the clothes—it was about his anxiety about feeling outdated in his fast-evolving industry. Once he recognized this, he became more open to subtle updates that helped him project the experienced but current image he wanted.
The sixth and final major mistake is dressing for an outdated version of yourself—specifically, continuing to wear the same cuts and styles that worked for your body twenty years ago. Our bodies change throughout life, and cuts that flattered us in our thirties may not work in our fifties or sixties.
My uncle Bill’s high-rise, pleated pants might have balanced his proportions in the 1980s when he was carrying more weight in his chest and shoulders. But as he aged and his weight distribution changed (as it does for most men), those same pants created an entirely different and less flattering silhouette.
The solution isn’t drastically changing your style, but rather honestly reassessing what flatters your current body. This might mean adjusting rise height on trousers, reconsidering the button stance on jackets, or changing collar styles to better frame your current face and neck.
So what happened with my clients? Michael, the tech executive, made thoughtful updates to his wardrobe—nothing drastic, just strategic improvements in fit, silhouette, and subtle incorporation of texture and color. Three months later, he emailed me: “For the first time in years, someone asked for my opinion in a meeting without prefacing it with ‘as someone who’s been in the industry for a long time.'” People were responding to him as a current player, not a relic, simply because he looked the part.
Gregory, the professor, updated his eyeglasses, improved the fit of his shirts, and incorporated more texture into his academic wardrobe. “My student evaluations actually mentioned that I seemed more ‘engaged’ and ‘present,'” he told me, laughing. “I’m teaching exactly the same material in exactly the same way. I just don’t look like I’m stuck in 1995 anymore.”
As for my Uncle Bill? After his retirement, my aunt quietly orchestrated a wardrobe refresh, using his newfound golf enthusiasm as an excuse. The updated, better-fitting clothes didn’t make him look younger in any artificial way—he still has his gray hair and laugh lines—but they stopped actively adding decades to his appearance. He looks like himself, not a caricature of an old man.
The goal isn’t to chase youth or reject aging. It’s simply to ensure your style choices aren’t artificially aging you beyond your years. Contrary to what many men fear, updating these elements doesn’t mean dressing “young” or inappropriately—it just means dressing accurately for who you are now, not for an outdated idea of what age-appropriate means.
Because here’s the truth: there’s a massive difference between dressing in a way that acknowledges your actual age and dressing in a way that adds fictional decades to your appearance. You can’t control the passage of time, but you can absolutely control whether your style choices are working with you or against you. And sometimes, the most age-appropriate choice is the one that doesn’t scream “I’ve surrendered to obsolescence” from across the room.
