Last month I went shopping at a thrift store near my house in Lincoln Park and found a windbreaker that looked just like the one my dad wore when I was growing up. Exact shade of teal. Exact shitty reflective stripes.
It wasn’t a 100% match though. The sleeves were several inches too long and it zipped up in the front rather than buttoning like my dad’s did. I looked in the mirror and caught my girlfriend Sarah staring at me. “Isn’t that literally your dad’s jacket?” She asked.
I froze, horrified by my body’s betrayal. It fit me though.

Well… kinda.
It fit my body well and flattered my figure without trying too hard. Those awful perfect neon green stripes actually looked kind of cool against the navy blue zipper. I ended up buying it. $35 well spent.
Later that week I wore it out with a pair of black jeans and my white leather trainers. Three separate people told me how good I looked. THREE PEOPLE!
Yep…I’m officially reaching an age where my closet slowly begins to look like my dad’s. One terrifying style trend at a time, I’m morphing into my dad’s hustler/Michael Jordan/music lover/football fanatic ruin. I promise I’m not mad about it though.
Ever since I can remember my dad has kind of been a fashion don at life. Blue collar worker who purchased clothes that looked comfortable and got the job done, but neglected fit 100%. He’;s owned an obscene amount of windbreakers (What did dads even do with all these windbreakers in the ’90s?) Several pairs of light-wash jeans that embodied every wannabe country singer’s dream outfits, and some brutally white New Balance trainers that he wore with basically everything.
I remember laughing at him for wearing those trainers with white crew socks pulled up to his knees paired with some awful basketball shorts orcargo shorts that were literally designed with enough pockets to feed an entire family of four living in rural India. This was peak embarrassment when I was 14 years old. Hell, if we were walking around the mall and I had to pass him I would purposely take extra wide turns so as to not appear near him.
Last weekend I found myself staring into my closet debating over which pair of chubby trainers I should wear to casually run errands. One was a pair of grey New Balance 990s I bought for $180 (…read: stolen straight out of my dads closet circa 2000) and the other was some equally gross pair of chunky Nike trainers. What did my life become?
You see, the fashion industry has clearly decided to fully adopt every single trend we made fun of when referring to as “dad style” and I’ve been slowly consumed by it kicking and screaming. Chunky trainers? I’m wearing them.
On opposite feet. That “effortless” ( effortless as in my dad woreit, not how we wear it today ) relaxed fit he wore in the mid-90s that I spent years torturing my legs in ill-fitting skinny jeans? Yeah I’mmm falling for it too.
Don’t get me wrong, I totally get it though. Comfort and ease of movement are something we can all stand behind, even if we weren’t wearing our values literally hung off our sleeves back when we were in high school. We aren’t looking to dress exactly how our dads did in their prime decades, we’ re taking little tid bits of their old style and using them to inspire a more modern, mature wardrobe that values comfort first and looks good second.
These dad style trends are coming back into style because they work, not because you’re teenager wants to make fun of their pops. There’ s one key difference between guys wearing these “dad styles” now vs how your actual father is wearing them. Intentions.
My dad’ s neighbour wears his grey New Balance trainers 993s with his pleated khakis and polo tucked into his ghetto ass belt on purpose. He looks like he’s about to go into Home Depot and spend the day deciding which Allen wrench he likes better. I can throw those same damn trainers on with some cropped trousers, bold socks, and an oversized jumper or blazer and I instantly look like I’ m starring in the next Vogue America cover.
We’ re both wearing the exact same shoe but our outfits are telling two totally different stories. Chunky dad trainers were my enemy for the longest time. I swore I’d never let those babies touch my feet.
My younger self stubbornly refused to give them a chance because of how they made me remember feels I got when dads wore them 10 years ago. Instead I stuck to my thin white leather trainers that provided barely any coverage on the bottom half of my foot. One of my friends finally talked me into trying on a pair of New Balance 990s and I was done for.
Not only were they comfortable (obviously) but I caught a glimpse of myself in the mirror and realised they didn’t look completely disgusting with my slim fit black jeans and bomber jacket. I now wear those trainers whenever I travel. They’ve got me through both O’Hare and LaGuardia airport without my feet feeling like they wanted to shut down.
Something my fancier trainers would’ ve immediately blister at the thought of if I wore them anywhere farther than Brooklyn. My dad saw those when he was visiting Chicago a few months back and chuckled. “Man I remember paying like sixty bucks for these things!” He texted me when we were at Sears “Good thing you finally got a pair with some actual cushion.” Buddy hasn’t gained or lost an ounce or a single outfit combination since,what does he know? Fleeces are another trend that dads loved back in the day and are now slowly making a comeback.
Before they were exclusively for hiking Mount Everest and staying indoors while your kids played sports every Saturday morning, now everyone is rocking them. Yep, they’ re in my closet too. I own not one, not two…but three fucking fleeces.
I own a brick red one I picked up from some Japanese brand I refuse to admit I shop at that was more expensive than my dad spent on his entire fleece collection growing up. THEN I found this vintage Patagonia at my local thrift store. Styling these bad boys correctly is important.
I’ll wear the red one over a plain white tee with some wide leg trousers and loafers, or layer the Patagonia underneath an oversized wool coat with some dark wash jeans and boots. Taking my dad’ s old Sunday best fleece and putting a more tasteful spin on it. I wore that red one out to brunch a few weeks back and some dude ( clearly older than me) stopped me in the middle of the street to ask where I got it.
Said someone almost definitely told his sons not to dress like their Uncle Jeff right now. Poor bastards. Oh Fanny packs.
How they’ ve made a resurgence. International symbol of dads on holiday is literally the last thing you’d want to sport unless you were actually taking a family trip to Disneyland. Everyone’s dads wore them loaded up with sunscreen, band-aids, and whatever other surprises dads thought they’ d need to bring their children to places with glass all over the floors.
Jump forward to present day and major brands are crafting these “belt bags” (yes thats what we’re calling them now. Literally beltsack) out of leather and everyone is wearing them across their bodies rather than down at their waist. I now own two.
One thin black nylon one I slip on whenever I need to run errands and a thicker, more “technical” outdoor version I take with me whenever I fly. The functionality is nearly the same as what my dad had clipped to his waistband when he went camping as a child, but wearing it across my body instead of my hips has given it an entire new vibe. One that’ s a lot more “I intended on wearing this ” than my dads.
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My dad saw the skinny leather version I bought him for fathers day dying a little inside. “Forty dollars for something that small?! ” he texted me when I showed him. Old fanny pack was $12 at Walmart. Guy jeans are back.
THANK GOD. Tight leg, giant circumference, light wash jeans that your dad insisted looked “so good on him” aren’t what everyone is wearing now when these babies came back in style, but everyone wants to wear them. Luckily the jeans that ARE popular now actually fit unlike my dads glorified hammock.
They’ re not baggy enough to make me look like him leaning against a wall, but slim through the thigh and cut off just right at the bottom to actually provide some shape. I snagged a pair of vintage Levi’s 550s that could’ve passed for my dads if he decided to wear them. Except I kept myself somewhat modern by swapping out his weathered trainers for some Chelsea boots and tucked in t-shirts.
Or loafers and blazers. Not white trainers and a polo t-shirt. Comfort has been my saving grace.
I used to sit in jeans so tight I could barely breathe, now I’ m appreciating how amazing it feels to have room to move around. I’m sure my dad felt this way too, he just didn’t have the luxury of caring about “looking cool” when he was my age. Tucked in Tees.
FUCK DID I hate when dads wore these growing up. Sunday Funday in NYC must have been dermatology exams walking around with all the dads from New Jersey that would invade the LES looking for a spreadable bagel. Every single dad out there couldn’t resist putting their t-shirt tucked into their trousers and we made fun of them for years about it.
Guess what dads? Your damn kids were probably right. I was putting together an outfit one day with a plain white t-shirt and some chinos that were fuller cut around the leg.
Every time I took a step my shirt would ride up and fuck with my jumper vibes I was going for. So I decided to just go ahead and tuck it in to see how stupid I looked. My girlfriend stopped in her tracks and gave me a look. “ Dude that looks really fucking good though!” She replied.
Bet. I paired that shirt with some bootlaces and was honestly shocked at how much I liked it. It created this clean line that flowed with the rest of my outfit.
Instead of looking like I threw it on, I looked like I actually tried. I wore that outfit home to Long Island and my dad literally stopped me on the street. Pointed at my perfectly tucked in shirt and chuckled. “Son, you spent 20 years making fun of me for doing that!” The look he shot me was if he ever let me come visit again but damn did I feel good proving him right.
You better believe dad style jackets are making a comeback too. Who would’ ve thought that your average fishing vest would go from doubling as a Portable Storage Chest For Aaron back family holidays to menswear streetwear??? I didn’t!
Mine is a canvas style one I got from some workwear brand in navy and I wear it over a hoodie with some wide trousers and boots. It looks so incredibly intention , I can’ t even imagine dad wearing it while hiding in the woods waiting for trout. They even have amazing pockets that I actually use when I’ m out and about in the city.
Phone, wallet, headphones, notebook, keys, sunglasses. I got you pops. It’s like my dad’ s vest but optimised for 2021.
Same concept goes for baseball caps. Mine are a hell of a lot slimmer than the collection my dad has from Old Faithful Golf Course and every shitty sports team he rooted for as a kid. Not one of his hats don’t have a sweat stain around the band either. ( brag ) His also ALWAYS have some aggressively curved brim.
My hats are nice and fitted to my head with 100% straight brims. I haven’t had the guts to fully embrace dad socks and sandals just yet, but I did break out my Birkenstocks with some sock cotton ball peeking through when I was in Europe this past Spring. Every time I stepped down on the cobblestone streets of Florence my inner teenage self died just a little bit.
My feet on the other hand were rejoicing. My dad has been rocking that look for years the minute weekend temperatures reach 60 degrees and isready to venture out to get the Times. I probably will apologise to him one day for being such a douchebag.
Most likely not anytime soon though. Here’ s the thing about rocking these previously dad only trends. Don’t wear all of them at once.
You can’ t dress like your grandfather and expect to fit in with the dudes of today. Going full Drake circa 2016 is inspiration cosplay, it’ s not irony. Throw on one or two elements you like and build your outfit around that.
Maybe some joggers with a new jumper, or a stylish blouse under an old school overcoat. Those thick dad trainers? Streetwear favourite.
Old pair of dad jeans that you distressed at the knees? STILL dad until you style them with as much intention as the rest of your outfit. Fit also matters.
While we’ re leaning towards bigger and roomier fits with our clothing, there’ s a huge difference between baggy and offensive. Jackets, trousers, shirts, hell even shorts these days are still tailored in a way that flatters your body. They may be oversized, but they fit you for a reason.
Your dads clothing fits him perfectly…because it was made to fit him. You and your dad probably have completely different builds which is why you should be buying clothes that fit YOU, not him. And for fucks sake make sure you’ re buying quality pieces that will actually fit well.
Dad style clothing was made to be durable and (hopefully) warm, not look good. These aren’ t your fathers polyester blends. These are made with just as much detail into the texture of the fabric, weight, colour, and cut.
Practical? You bet. But also stylish as hell.
I’ll give my dad some credit, though. He never saw any of this coming. Still wears literally the same things he did when I was in elementary because he likes them and they work for what he needs to do.
I can only imagine his face when he finds out his grown ass son is buying barely worn versions of his wardrobe at retail price. Give him a call. Let him know his styling method has officially gone viral. “ So I should expect you rocking white trainers with a fanny pack and socks with sandals when I see you at Christmas?” He laughed at me. “ Don’ t push it kiddo.” Some dads jokes I will never let him live down.
At the end of the day I’ ve learned that being comfortable doesn’t have to be the complete opposite of looking awesome. Jeans that allow you to breathe just take some extra care to not look like they’re begging you not too.




