My Dad’s Terrible Style Is Suddenly Cool (And I’m Having an Identity Crisis)

Last month I caught myself trying on a windbreaker at a thrift store in Lincoln Park that was basically identical to one my dad wore throughout my entire childhood. Same aggressive teal color, same weird reflective strips, same boxy fit that makes you look like a walking tent. My girlfriend Sarah watched me examine myself in the tiny mirror and said, “Isn’t that exactly like the jacket you used to make fun of your dad for wearing?” I froze, windbreaker half-zipped, confronted with this deeply uncomfortable truth.

The thing is… it looked good. Not amazing, but good. Better than good, actually. I bought it for thirty-five dollars and wore it the next week with some black jeans and my white leather sneakers. Got three compliments. Three! For wearing something I literally mocked my poor father for owning when I was sixteen.

This is where I am now, apparently. Slowly becoming everything I once swore I’d never be, one dad trend at a time. And honestly? I’m not even mad about it anymore.

Growing up, my dad’s closet was this fascinating disaster of practical choices and complete aesthetic blindness. The man owned multiple windbreakers (why did dads in the ’90s need so many windbreakers?), light-wash jeans that would make a country music star jealous, and these blindingly white New Balance sneakers that he wore for literally everything. Grocery shopping, yard work, taking me to soccer practice, you name it. Those shoes were his uniform.

I remember being mortified watching him pair those sneakers with white crew socks pulled up to mid-calf and cargo shorts with approximately seventeen pockets. At fourteen, I was convinced this was the most embarrassing thing a human could wear in public. I’d walk ten feet behind him at the mall, pretending we weren’t related. Peak teenager behavior, I know, but his style choices felt like a personal attack on my social standing.

Fast forward to last weekend and I’m standing in my apartment trying to decide between two pairs of chunky sneakers for a casual dinner. One pair is gray New Balance 990s that cost me $180 and look suspiciously similar to my dad’s old favorites. The other is a pair of chunky Nikes that are somehow even bulkier. When did this become my life?

The fashion world has completely rehabilitated what we used to call “dad style,” and I’ve been slowly, unwillingly sucked into it. Those chunky sneakers I used to mock? They’re now the foundation of half my casual outfits. That relaxed fit my dad preferred over the skinny jeans I tortured myself with for years? Turns out comfort and style aren’t mutually exclusive. Who knew?

But here’s what’s wild – it’s not just about fashion being cyclical or ironic. These trends are coming back because they actually work. My dad prioritized comfort and functionality while I spent my early twenties squeezing into jeans so tight I couldn’t sit down properly. He could walk all day in those chunky sneakers while I was getting blisters from my “stylish” shoes after two hours. Maybe the old man was onto something.

The key difference between how dad style looks now versus how our dads actually wore it comes down to intention and context. My neighbor Mike still wears his gray New Balances with pleated khakis and tucked-in polo shirts, creating this look that screams “hardware store regular.” When I wear similar sneakers with cropped trousers, interesting socks, and an oversized sweater or blazer, it reads completely differently. Same shoes, totally different statement.

I resisted the chunky sneaker thing for years. Clung to my minimal white leather sneakers like they were the last symbol of my youth. Then my friend Marcus convinced me to try on those 990s during a shopping trip. The comfort was immediately obvious – like walking on clouds compared to my flat-soled alternatives. But what surprised me was catching my reflection and realizing they didn’t look terrible with my slim black jeans and bomber jacket.

They’ve become my go-to travel shoes now. Carried me through O’Hare and LaGuardia without a single foot complaint, something my stylish-but-impractical sneakers never managed. When my dad noticed them during his last visit to Chicago, he just smiled and said, “Finally got sensible shoes.” The smugness in his voice was unbearable, but also… earned.

Another dad staple that’s having a moment is the fleece zip-up. Remember when fleeces were exclusively worn by nature documentary crews and suburban dads at Saturday morning soccer games? Now they’re everywhere. I own two – a brick red one from some Japanese brand that cost more than my dad’s entire fleece collection, and a vintage Patagonia I found at a consignment shop.

The trick is pairing them with unexpected pieces. I’ll wear the red one over a white t-shirt with wide-leg pants and loafers, or layer the Patagonia under a wool overcoat with dark jeans and boots. Same basic garment my dad wore to parent-teacher conferences, but styled in ways that feel intentional rather than accidental.

Last month I wore the red fleece to brunch and a stranger actually stopped me to ask where I got it. This stranger was clearly younger than me and probably spending his teenage years mocking his own fleece-wearing father. The cycle continues, I guess.

Even the fanny pack has made this bizarre comeback. Remember when fanny packs were the international symbol of tourist dads? My father wore one to Disney World three different times, loaded with sunscreen, band-aids, and whatever other emergency supplies dads think they need for theme park survival. I was mortified every single time.

Now luxury brands are making “belt bags” (same thing, fancier name) and everyone’s wearing them crossbody instead of around the waist. I own two now – a sleek black nylon one for daily use and a technical outdoor version for travel. The functionality is identical to my dad’s Disney World special, but somehow wearing it across my chest instead of around my waist transforms it from dorky to deliberate.

My dad finds this development hilarious. “Forty dollars for that little bag? Mine was twelve bucks at Walmart!” he texted when I showed him my newest acquisition. He’s not wrong about the price difference, but he also still tucks his t-shirts into his shorts, so we’re operating from different style philosophies.

Dad jeans have also made this spectacular return, though with better proportions. Those light-wash, relaxed-fit jeans that dominated every suburban mall in the ’90s are back, but they’re actually cut well now. Instead of the shapeless disasters that pooled around my father’s white sneakers, today’s versions have thoughtful proportions – relaxed but not baggy, often cropped, with a higher rise that actually flatters.

I’ve embraced a pair of vintage Levi’s 550s that would’ve looked perfectly at home in my dad’s 1995 wardrobe. Faded light blue, relaxed straight leg, higher rise than anything I wore in my skinny-jean years. The difference is all in the styling – I wear them with Chelsea boots and turtlenecks, or loafers and blazers, instead of white sneakers and polo shirts.

The comfort revelation has been huge. After years of fighting my way into jeans that required strategic breathing, having room to actually move feels revolutionary. My dad probably knew this all along, but prioritizing comfort over fashion wasn’t exactly cool when I was twenty-five and thought suffering for style was virtuous.

Then there’s the tucked-in t-shirt situation. This move was the absolute hallmark of dads at backyard barbecues when I was growing up. Every father in America seemed constitutionally incapable of wearing an untucked tee, and we mocked them relentlessly for it. Turns out they might have been onto something.

I discovered this accidentally. Was wearing a plain white t-shirt with some wider-leg chinos and a vintage belt, and the shirt kept riding up weirdly. Finally just tucked it in to see how it looked. Sarah stopped mid-conversation and stared. “That actually looks… really good?” The surprise in her voice matched my own confusion.

The proportions worked in a way I hadn’t expected. Created this cleaner line that made the whole outfit look intentional instead of lazy. When I visited home wearing this exact combination, my dad literally pointed and laughed. “You spent twenty years making fun of me for that!” His vindication was complete and thoroughly earned.

Even practical dad outerwear has been reclaimed by fashion. The fishing vest – once worn exclusively by actual fishermen and dads who needed seventeen pockets for mysterious purposes – has been reinterpreted as a layering piece by brands from Tokyo to Brooklyn. I never thought I’d own a vest that’s never seen a fish, but here we are.

Mine is navy canvas from some workwear brand, and when I wear it over a sweatshirt with wide pants and boots, it somehow looks deliberately fashion-forward instead of like I got lost on the way to Bass Pro Shops. The multiple pockets are genuinely useful for city life too – phone, wallet, headphones, notebook, keys, sunglasses. Turns out dad practicality and style can coexist when you execute it thoughtfully.

Baseball caps have undergone a similar evolution. My dad’s collection features various golf courses and sports teams, usually with sweat stains around the band and aggressively curved brims. The modern version favors cleaner designs, better materials, straighter brims. My favorite is a simple navy wool version with no logo – miles away from my dad’s aesthetic but serving the same basic function.

I haven’t fully committed to the socks-with-sandals revival yet, though I’ve experimented with Birkenstock clogs worn with visible socks during spring weather. Each time I do this, my teenage self dies a little inside, but the comfort is undeniable. My dad, who’s been wearing tube socks with rubber slides to get the newspaper every Sunday for my entire life, probably deserves an apology I’m not ready to give him yet.

The secret to wearing these reclaimed dad pieces without looking like you’re chaperoning a field trip comes down to a few key things. First, it’s about selective adoption. You can’t wear every dad trend simultaneously – that’s not ironic, that’s just a costume. Pick one element, maybe the chunky sneakers or the fleece, and pair it with more contemporary pieces.

Second, fit still matters enormously. Yeah, silhouettes have relaxed, but there’s a huge difference between deliberately oversized and just poorly fitting. Even the roomiest contemporary cuts are designed with intention. Your dad’s actual clothes worked for him (sort of), but unless you share his exact body type, you need pieces cut for you.

Third, quality and materials make all the difference. The technical fabrics and thoughtful construction of today’s “dad” pieces separate them from the discount originals. My father’s fleece was chosen purely for warmth and bought on sale. Mine considers texture, weight, color, and cut – practical yes, but also aesthetic.

The funniest part of this whole dad style renaissance is that most actual dads remain completely oblivious to it. My father still wears essentially the same uniform he has for decades, totally unaware that his practical choices are now being sold at premium prices to fashion-conscious guys like me.

When I called to tell him his style had finally become cool, he just laughed. “So I can expect to see you at Christmas in white sneakers, a fanny pack, and socks with sandals?” I told him not to push his luck. Some dad trends are still bridges too far. But given how many of my former mockeries I’m now embracing, I probably shouldn’t bet against it.

Maybe the biggest lesson here is that comfort and practicality – values my dad championed while I chased trends and suffered for style – aren’t actually incompatible with looking good. They just needed better execution. So next time you mock your father’s wardrobe choices, remember that in ten years you might be spending serious money to dress almost exactly like him. Just hopefully with better color coordination than whatever was happening in the ’90s.