I turned 35 last month, and it hit me hard. Not because I’m afraid of getting older—honestly, my thirties have been way better than my twenties in almost every respect—but because I realized I was wearing the exact same outfit I’d worn on my 25th birthday. Same style of slim dark jeans. Same type of white sneakers. Same oxford cloth button-down, sleeves rolled to the elbows. The specific items were newer versions, but the look was identical. A full decade had passed, and my style had apparently been frozen in amber.
This sent me into a mild existential tailspin. Should my style have “grown up” more? Was I that guy desperately clinging to youth? Or was I just sticking with what works? I mean, it’s not like I was trying to rock skinny jeans and a graphic tee from Hot Topic. But still, the question nagged at me: Is there such a thing as dressing appropriately for your age in 2025, or is that concept as outdated as matching your belt to your shoes?
To answer this, I did what any self-respecting style writer would do—I called up men of various ages whose style I respect and asked them how their approach to dressing has evolved over the decades. The conversations were enlightening, occasionally hilarious, and surprisingly emotional.
“Your twenties are for fucking up,” said Martin, a 58-year-old creative director whose office I’ve been lowkey style-stalking for years. “Sartorially, I mean. I wore leather pants in my twenties. Actual leather pants. With fringe. There are photos. They will be burned before my funeral.” But he made an excellent point about those experimental years: “You need to get all that crazy shit out of your system. Try everything. Figure out what actually works on your body and with your personality. The guys who don’t experiment young are the ones who have midlife crises and show up in Balenciaga sneakers at 50.”
I thought back to my own twenties style journey. The unfortunate year of attempting to dress like an extra from Mad Men (too costumey). The “statement blazer” phase (too peacocky). The minimalist all-black period (too barista). Each seeming failure was actually valuable data gathering—learning what felt authentically like me versus what felt like I was playing dress-up.
Talking with guys in their twenties now, I notice they seem both more liberated and more anxious about style than my generation was. Ricky, a 24-year-old who works in tech, told me, “There are no rules anymore, which is cool but also kind of paralyzing? Like, I can literally wear anything, but then how do I know what’s right?”
What’s fascinating is how much of his anxiety stemmed not from fear of looking too young, but fear of looking prematurely old or boring. “I don’t want to dress like I’ve given up, you know? Like some generic guy in chinos.”
This gets at something important. Age-appropriate dressing isn’t about following arbitrary rules like “no jeans after 40” (bullshit) or “all men must own a navy blazer by 30” (also bullshit, though navy blazers are genuinely useful). It’s about dressing in a way that respects your current life stage without surrendering to outdated expectations of what that should look like.
For your twenties, that might mean embracing the freedom to experiment while building a foundation of versatile pieces. Every twenty-something guy I spoke with expressed the same core tension: wanting to try bold styles while also needing practical clothes for entering professional settings. The smart ones approach this by investing gradually in quality basics (good jeans, well-fitting tees, a couple of decent shirts, one proper suit) while using less expensive or vintage pieces to play with trends.
My friend David, whose style has always been impeccable, spent his twenties thrifting Italian suit jackets and pairing them with band t-shirts and paint-splattered jeans. “I was an assistant making $32,000 a year in New York. I couldn’t afford to buy a whole new professional wardrobe, but I could spend $40 on a secondhand Zegna blazer and wear it over clothes I already owned.” His style was distinctive, appropriate for creative industry events, and worked within his budget constraints.
The thirties shift happens organically for most guys, coinciding with career advancement, maybe serious relationships or family responsibilities, and—let’s be honest—a metabolism that’s becoming less forgiving. The men I know with the best style in this decade have mastered the art of looking put-together without looking stuffy.
“Your thirties are when you figure out quality over quantity,” said James, a 41-year-old architect whose minimalist-but-never-boring style I’ve always admired. “In my twenties, I had a closet full of cheap crap. Now I’d rather have three great shirts than ten mediocre ones.” He’s nailed what I think of as the thirty-something sweet spot—clothes that fit perfectly, fabrics that drape well, and a clearly defined personal aesthetic that works across multiple contexts.
My own thirties evolution has been subtle but meaningful. I’ve gradually upgraded fabrics and construction (goodbye, fast fashion; hello, year-round wool trousers). I’ve refined my color palette to what actually works with my complexion rather than whatever’s trendy. And I’ve started investing in proper shoes now that I’ve finally accepted that cheap ones both look bad and feel worse as your feet become less forgiving.
What I haven’t done is suddenly pivot to dressing “more mature” based on some arbitrary birthday threshold. I still wear sneakers, just more refined ones. I still wear jeans, just better ones with a fit that flatters my no-longer-twenty-five-year-old body. The vibe is evolution, not revolution.
This approach continues into the forties, where the best-dressed men I know have achieved something remarkable—they look appropriate and current without looking like they’re trying too hard in either direction.
“Comfort becomes non-negotiable, but that doesn’t mean giving up style,” explained Michael, a 47-year-old professor whose relaxed-but-refined wardrobe manages to look simultaneously authoritative and approachable. “I used to wear dress shoes that hurt because they looked good. Now I’ve found brands that don’t kill my feet but still look sharp. Same with everything else—the fit has to work with my actual body, not some imaginary ideal from when I was 25.”
This gets at something crucial about dressing well as you age: it requires honest assessment of your current reality, not nostalgia for your former self. The forty-something guys who look best have adapted to their changing bodies rather than fighting against them or giving up entirely. They’ve found cuts that flatter their current physiques, and they’ve developed a confident personal style that isn’t driven by fleeting trends but isn’t willfully outdated either.
By the fifties, the men with the best style have usually developed a signature look—not a uniform, exactly, but a consistent approach that feels authentic and intentional.
“I know exactly who I am now,” said Richard, a 56-year-old creative consultant who still regularly appears in street style photos despite (or perhaps because of) his silver hair. “I’m not chasing trends, but I’m not stuck in the past either. I wear what makes me feel like myself.” His wardrobe revolves around beautifully made basics with subtle details and impeccable fit, plus the occasional statement piece that keeps things from getting too predictable.
What I’ve noticed across all these conversations is that truly stylish men of any age share one quality: they dress for their current reality, not an idealized past or future version of themselves. The twenty-somethings aren’t trying to look 40, and the fifty-somethings aren’t trying to look 25. Everyone’s clothes actually fit their current bodies. They’ve all found the sweet spot where personal taste, lifestyle requirements, and physical reality converge.
The guys who struggle most with age-appropriate style are the ones fighting against their current circumstances rather than working with them. The forty-something squeezing into the same cuts he wore in college. The thirty-something who preemptively adopts an older man’s wardrobe out of some misguided attempt to look “serious.” The fifty-something who suddenly starts dressing like a hypebeast because he’s afraid of becoming invisible.
So what does this mean for my own style frozen-in-amber moment? After these conversations, I realized I don’t need to drastically change how I dress just because I’ve hit 35. But I should be honest about whether my current style truly serves my current life.
Some aspects still work perfectly—the well-fitting Oxford shirts, the quality dark jeans. But other elements could use updating. Those slim-fit chinos from 2015? They’re fighting a losing battle with my post-pandemic body. The ultra-minimal white sneakers that once felt fresh? They’ve become such a generic millennial uniform that they no longer say anything interesting.
The key isn’t to scrap everything and start over. It’s to evolve thoughtfully, keeping what works while being honest about what no longer does. To invest in quality pieces that actually fit my current body. To dress for the life I have now, not the one I had a decade ago or the one I imagine having a decade from now.
The most liberating realization from all these conversations? Age-appropriate style isn’t about following generational rules. It’s about authenticity, context, and self-awareness. The 25-year-old in a well-cut suit for the right occasion looks just as age-appropriate as the 55-year-old in well-fitting jeans and a cashmere sweater.
So I’m making small, meaningful adjustments. Embracing slightly more relaxed fits that flatter my current body. Investing in better fabrics that drape well. Focusing on versatile pieces that work for my actual lifestyle—which now includes occasional TV appearances and industry events—rather than an imagined ideal of how a 35-year-old “should” dress.
When I mentioned this approach to Martin (he of the regrettable leather pants), he nodded approvingly. “The best style advice I can give any man, at any age, is simple: dress for who you actually are, not who you think you’re supposed to be. Everything else is just details.”
That’s wisdom worth waiting 58 years for—and way more useful than any arbitrary rule about what you can or can’t wear after a certain birthday.
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