Why I Wore the Same Outfit for 10 Years (And What It Taught Me About Dressing Your Age)

There’s this picture of me in high school dressed as Don Draper for Halloween. Looking exactly like I borrowed dad’s suit and literally put a costume together. Why didn’t anyone stop me?

Or buy me a millennial-gray flannel instead?

There was also that disastrous period when I was convinced that statement blazers were my brand. Spoiler: They were not.

Through every ill-advised trend I stumbled through as a teenager and young adult, Martin was right – I was learning what worked for me and what didn’t. Started to notice how certain styles made my hips look huge or how certain colors made me look washed out when they looked great on other people.

Hell, I was even comparing myself to other men more to see what looked good and what didn’t. Like this kid Ricky who works at my school teaching computer classes. He’s probably about 24 and has somehow mastered the whole college-student vibe. We were chatting and I asked him if he ever worries about dressing too young for his age.

“I don’t want to look boring,” he said, which to me meant old. Not like immature, he meant old-old. “Like I gave up?”

I thought that was interesting because it’s the total opposite of what most people worry about when they hit 30. We’re afraid of dressing too young, not too boring.

And Ricky has plenty of company in his pants-less polo shirt wearing cohort.

Were dudes in their thirties and forties this stylish in the 90’s?

Back then it was more or less implied what guys should and shouldn’t wear based on age. Dad wore dad jeans and polo shirts because that’s what men wore when they reached his age. Grandpa wore slacks and button-ups because that’s what his generation wore.

sneakers when you hit your teens, nice dress shoes when you’re in your twenties, cute comfortable shoes when you’re older but can’t pull off sneakers anymore, white New Balance by the time you turn 60.

Now everyone’s clothing timeline is thrown out the window. I see 50 year old dudes rocking Supreme as casually as my coworkers wore it in college. Some pulling it off, some not, but most just way older than we remember our 17-year-old-self wearing them.

I see guys in their mid-twenties rocking three-piece suits with whipping coats. These weren’t old-timey suits my grandpa would wear, they were modern, slim cuts.

I can’t help but think what I’m seeing now is a direct result of everyone dressing how they want not what society says they should at their age.

I talked to dudes younger and older than me to find out what they thought made men look their best at any age. The overwhelming consensus? The best-dressed dudes are the ones who are actually being themselves.

Not trying to dress like someone half their age or someone twice their age. The young guys buying quality clothing that fits instead of pricey brands they see celebrities wearing. The older guys who’ve learned to relax dressing like a total hipster just to look cool.

Hell, my friend David thrifts awesome vintage Italian blazers in his spare time. Started doing it when he was a twenty-something earning 30K a year living in New York and couldn’t afford “new professional clothes.” Instead he’d scour thrift shops every weekend for old oversized suit jackets and pair them with vintage band t-shirts and jeans.

Looked expensive, not cheap. Edgy, not try-hard. Now he’s in his late-thirties and still rocks an updated version of his twenty-something scheme. Jeans that actually fit properly instead of letting himself into thrift store jeans that used to fit. Tees he actually bought at Target instead of stolen from his older brother’s closet.

…and yes, some he still thrifts.

He never “grew out” of his crazy Brooklyn thrift phase, he just elevated it to what suits him best now.

I’ve been doing this myself without even realizing it.

Remember how I said those $15 clearance jeans from my freshman year of college made me look like I stole my lil brother’s pants? Gone. Upgraded to waist sizes that actually fit my not-19-year-old body.

Cheap dress shirts that looked liked hanged from my shoulders? Slowly replaced by shirts that don’t make me sweat through the first class of the day.

I still shop at most of the same places as I did ten years ago, I’ve just become a little bit smarter about what I wear and how it fits my body.

I have resisted some changes too though. I still wear the same brand of minimalist white sneakers I did in college. Except now literally every other guy my age is wearing the same damn things. “Y’all look like a millennial uniform,” Jessica teases.

But THEY FIT WITH EVERYTHING.

So here’s the big difference between how I dressed at 25 and how I dress now. Back then I settled for what I could afford because I didn’t have much of a budget. Everything was $20 or less because honestly why spend more? Now I can actually afford to buy a $40 shirt instead of one that costs half the price.

Not talking expensive shirts here, but noticeably better shirts.

Quality over quantity, my friend James likes to call it. He’s an architect and has always been way sharper than I gave him credit for in high school. “When I hit my thirties I finally had the cash and wisdom to invest in clothes that fit and looked good. Used to own a closet full of junk I didn’t want to wear. Now I’d rather have three shirts that I love than ten that I’re OK with.”

He hit the nail on the head. Everything he owns fits him perfectly. Brands that don’t look or feel cheap. And best of all, he has a defined sense of style that he can dress up or down. Meets with clients? Coordin hoodie and vintage shirt. Chill with us old guys? Same hoodie, but a nicer shirt.

The dudes who never seem to age gracefully are the ones who either refuse to change or go to the complete opposite direction. Old high school teacher I used to have still wears the exact same baggy jeans and XXL PT Torment polo shirts he did in the early 2000’s. Guy borrowed his older brother’s clothes and never took them back.

And then you have guys who hit a certain age and decide they need to dress like their grandfathers. Suddenly every outfit is coordinated around some juicy pair of slacks and boring button-up.

Hell, I even asked a few older guys I admire what they thought made guys look good at any age. Michael is my neighbor who teaches environmental science at the local community college. Big reason I respect his style; he’s 47 but rocks clothes I’m legitimately jealous of.

“Comfort becomes key,” he told me. “But that doesn’t mean you can’t look good. Just took me a while to find pants that fit well and weren’t going to kill my feet.” Makes sense. Ain’t nobody got time for that anymore.

“I also realized my clothes had to fit my actual body, not this imaginary skinny-verse version of myself.”

That might be the truest thing anyone’s said to me about age and style.

Your body changes as you age. Not better or worse, just different. Denying that only makes your clothes look stupid.

So this year I got rid of some clothes that were no longer serving me just because I was used to them.

Those tapered chinos I wore constantly post-college aren’t suiting my body anymore. Granted I haven’t packed on the quarantine fifteen or anything, it’s just…the small of my back is bigger now. Clothes just aren’t shaped how they used to be.

I got rid of my old skinny pants and replaced them with pants that fit this new version of me.

Clothes that actually fit my lifestyle. Teaching middle school isn’t a walk in the park so comfort is important. But I have to wear stuff Jessica deems attractive when we go on dates. Girl still wants me to dress nice for our once-a-week “adult dinner” dates.