Last week I went shopping for new undershirts at Target (kids, being a middle school teacher is so glamorous) when I caught a glimpse of myself in one of those mirrors by the checkout counters. …I was wearing literally the exact same thing I did on my birthday when I turned 25. Okay, not EXACT same formula. But dark jeans, white trainers, tucked in button-up with rolled up sleeves?
Same same. Getting old enough to shop for that pile of Hanes feels like both cementing your personal style and resigning yourself to fashion death all at once. Have you ever wondered if you’ve just been coasting since high school without even knowing it?
Dude, that was me holding three white t-shirts. …but then I started wondering, does dressing your age even still exist? Are guys in their thirties still making it up as they go?
Cause I’ve seen twelve year olds with better outfits than adults I see shopping at Publix.
I asked around. Colleagues at work who I thought kept stylish, old friends from high school, guys I always assumed dressed nice but never once asked how their day was. If I felt like I had hit a style plateau at 34 there were bound to be other dudes with opinions.
Funny story, there are A LOT of dudes questioning themselves on this topic. My friend’s dad, Martin, is a creative director of some fancy schmancy ad agency job and always looks put together without even trying. Something I will never achieve.
We started talking and got on the topic of dressing for your age. He busts out with this… “You spent your twenties screwing up your style.” Martin went on to tell me about his phase of wearing leather trousers. “With fringe! Kids, there are photos floating around my house that my wife has said she will show you.” After he stopped chuckling about his badass leather trousers he dropped some more knowledge on me… “You have to wear all the stupid shit when you’re young.” Martin explained. “Try the crazy colours, the weird styles and fits.
Figure out what looks good and what doesn’t work for you.” Ding Ding Ding!! ! I spent my whole twenties wearing skin tight acid wash jeans meant for adults half my age, clothes meant for Euros that didn’t account for American waistlines, and going through a phase where I thought sweatpants and black vans made me look “cool.” (That Netflix and Milk Bears instagram confirmed). Not every phase, shirt, and shoe combo I tortured myself with, but enough mistakes to learn from.
There’s a photo of me from high school dressed as Don Draper for Halloween. Except I don’t look like Don Draper in a classy suit. I look like I raided my dads closet and threw clothes together for a costume.
Why didn’t someone stop me?!? ! Why didn’t someone buy me some millennial grey trousers instead?! ? Also I went through this phase where I thought I looked sophisticated wearing statement blazers.
Spoiler alert: I did not. As crappy as each trend was, Martin was right – I was learning what looks good and what doesn’t work for me. Started noticing how big some clothes made my hips look or how some colours made me wash out when they looked great on everyone else.
DUDE, I was starting to pay attention to OTHER men to figure out what worked and what didn’t. Like my coworker Ricky. Yeah that kid right there.
This teenage unicorn masters that whole college-kid vibe. We were talking and I asked him if he ever worried about wearing clothes too young for his age. “I don’t wanna look boring.” Ricky said. As I’m pretty sure guys say boring, he meant old.
Old-old. “Like I gave up?” Mind blown. See most of us worry about wearing too young for our age. But what if we went TOO aged up? ?
And Ricky is not the only young-blood riding his v relaxing his clothes- Were guys this stylish in their thirties and forties when we were coming up in the 90’’s? Hell, we kind of KNEW what guys should and shouldn’t wear at each age. Dad wore dad jeans and polo shirts because that’ Bet his parents told him he had to by menswear when he was old enough to wear “big boy trousers.” Knew that once he hit his teenage years he could wear trainers instead of dress shoes.
By your twenties you wore cute but comfortable shoes because you were old enough to not wear trainers but too cool for dress shoes. And by the time you were his age, WHITE NEW BALANCE. One of the many reasons I think we’re seeing older dudes who dress like they’re half our age is because grown adults don’t know what they’re supposed to wear at their age anymore.
I talked to guys older and younger than me about dressing your age and what THEY thought helped guys look their best. Without a doubt answer I got? Be you, boo.
Stop trying to dress like your half or twice your age. Stop young guys thinking they have to wear expensive brands they see celebrities in. Older guys thinking they have to dress down because that’s “acceptable” for your age.
My friend David even hunts for vintage Italian blazers in his free time. Started when he was a low-key starving artist making 30K a year in New York and couldn’t afford buying “new professional attire.” So instead he’d hit the thrift stores every weekend to find old oversized blazers and pair them with vintage band shirts and jeans. Looked high end, not cheap.
Edgy and trendy, not trying too hard. Fast forward 10 years and David’s still doing his own thing. Only now he can afford clothes that actually fit him right instead of letting himself into oversized jeans from the thrift shop that USED to fit.
And of course he still thrifts. White tees he actually bought from Target instead of stealing from his brothers closet… He didn’t outgrow that vintage Brooklyn hipster phase, he evolved it into what makes him look best today. And guys..I’m doing the same thing without even realising it.
See how I said those Nordstrom Rack jeans I bought my freshman year of college shrink on me when I wash them? Gone. I wouldn’t dream of wearing trousers that don’t fit my waist anymore.
Let alone trousers that USED to fit my 19 year old body and now don’t. Cheap button ups that literally looked like they were choking me? Been replacing them one by one with better shirts that don’t make me sweat through my first period of the day.
Moral of the story- I still frequent most of the same stores as I did when I was in college, I’ve just learned to be smart about what I wear and how it fits my body. I will forever resist some trends though.. aka white trainers. Yep, I still wear the same brand of minimalist trainers I got in college.
Problem is, so does everyone else my age. “Y’all guys look like a millennial uniform.” Says my wife. But THEY MATCH ANYTHING! SO MANY COLOURS.
So here’s the difference between how I dressed at 25 and how I’m dressing now. See at 25 I bought what I could afford because I was on a college kid budget. My whole wardrobe consisted of shirts that were $20 or less because heck why spend more on a shirt?
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Now I can actually treat myself to a $40 shirt instead of one that’s half the price. And I don’t mean high-end shirts, guys. Just better shirts.
Got a lot better than what I was wearing at 25. My buddy James is an architect and man does he know how to dress. Smartest guy at my high school and I didn’t even realise it until we were adults. “I didn’t really invest in myself until my 30’s.
Finally had the money and sense of style to buy clothes that fit me and looked good.” Man I owned probably 50 shirts I hated dressing in back then. Now I’d rather have 3 shirts I love than 10 that I’m ok with. James said it best.
Everything he owns fits him nice and snug. Doesn’t have to worry about his clothes falling off or looking cheap. Plus, he has SUCH a defined style.
Dress it up or dress it down. Meetings with clients? Coordinate graphic hoodie and vintage shirt.
Hanging with us old folks? Same hoodie, but a nicer shirt. The guys that give other dudes aged look are the ones who refuse to evolve or go to extremes.
Old high school teacher I used to have straight up wears the same baggy jeans and XXL PT Torment shirts he did in 2003. Guy basically borrowed his brothers clothes in high school and forgot to give them back. And you have guys who suddenly decide they need to dress like their grandpas because of one number.
All of the sudden every outfit is built around some slim cut of slacks and boring white button up. I even asked some older dudes I looked up to for style advice. Michael is my neighbour who teaches environmental sciences at a local college.
Huge reason I trust Michaels style; he’s been my age and older but STILL wears clothes I’m jealous of. “Fit becomes more of your biggest style indicator,” Michael told me. “But that doesn’t mean you can’t dress well. Took me awhile to find jeans that fit my thighs and didn’t destroy my feet.” Preach brother. Nobody got time for that ish. “It also clicked with me that my clothes had to fit my REAL body, not this imaginary twig I thought I was in my head.” Couldn’t have said it better myself.
Your body changes as you age. Better, worse, just different. When you realise and accept that, your style will be better for it.
So this year, I tossed out clothes I been holding onto for way too long just because “it was my go-to.” Quit dressing like a 25 year old because..well I’m not 25 anymore! Remember those skinny jeans I mentioned before? They fit me perfectly when I left college.
Reason being, I haven’t gained the covid-19 shuffle twenty yet. It’s just, my butt is bigger guys. Realistically my body has changed in the past 10 years and I need to start dressing for my CURRENT body, not my college body.
Spent way too much time trying to squeeze into my skinny trousers that don’t fit me anymore. Instead I switched to jeans that fit my “new” me. Clothes that fit the person I am today.
Middle school might be “cool” but it’s not easy on the body. I gotta be comfortable. But I also gotta wear clothes that girlfriend thinks I look good in when we go on dates.
Ps-girlfriend still makes me wear nice clothes on our weekly “adult dinners.” Bless her heart is helpless against me wearing sweatpants. Girlfriend actually had me search all over Charlotte for these Carved Jeans because she thought they’d look good on me. Stopped in the weirdest place for this blog post of all places, Targets partner store Nine West.
And holy….moly. She was right. They look really damn good on.
Don’t believe me? Click that link guys. I’ll receive a small percentage (whole 15 bucks cause we ain’t rich!) and you get to look at the softest jeans I’ve ever felt.
Reminded me who I was wearing clothes for. Sure those skinny jeans were comfortable, but they weren’t flattering on me anymore. And I will never be Jennifer Lopez wearing skinny jeans at age 35.
Buying cheap shirts that shrank in the dryer didn’t save me money, it just made me look lazy and like I didn’t care. What pissed me off when I stared at that mirror was I didn’t like what I saw. I shouldn’t be embarrassed to wear these shirts around my wife.
They made me feel…basic. Plain. Average.
UGH I hate being average. I said I’m changing up my style. But doing it for the right reasons.
Things that I want to change and love wearing. Improving my staples and remembering why I like wearing clothes!
Best piece of style advice I received?
Listen to Martin. “Just wear clothes that YOU like. Not what you think you should be wearing.” Could’ve been the most simple advice in the world but it impacted me more than anything else I heard about dressing your age. 25 year old wearing a slim fit suit?
Dressing perfectly appropriate. Guy in his 50’s wearing jeans and a cashmere jumper? Still totally acceptable to wear (I will be buying my first cachmere jumper on my teacher’s salary someday… i swear.) Stop trying to dress for your age and just wear whats best for YOU.
Your body, your lifestyle, and your personality. As for those undershirts? Tossed those and went home.
Girlfriend knew something was up when I came home and walked around our flat walking like I just got shot. “What’s going on in that head of yours?” She asked after I word-vomited every thing I said about staring at myself in Target. Honestly friends…she married me for my personality, not my style. But Le HIGH TIME we kick these white trainers to the kerb.
