My dad’s closet was a fascinating horror show throughout my childhood. The man owned not one but three windbreakers in varying shades of teal and purple (it was the ’90s, but still). His collection of light-wash jeans would have made Jerry Seinfeld weep with joy. And the crown jewel of his weekend wardrobe was a pair of blindingly white New Balance 624s that he wore to mow the lawn, go to Home Depot, grill burgers, and pretty much everything else that didn’t involve his office job.
I remember swearing to myself at age 14, while watching him cheerfully pair those sneakers with calf-high white socks and cargo shorts, that I would rather literally die than dress like that when I grew up. The universe, it turns out, has a perverse sense of humor.
Last weekend, I found myself in a Manhattan vintage store trying on a mint-condition windbreaker in a shade that can only be described as “aggressive teal.” My girlfriend watched with a mixture of horror and amusement as I admired it in the mirror. “Isn’t that exactly like the jacket you used to make fun of your dad for wearing?” she asked. I paused, windbreaker half-zipped, confronted with the terrible truth: I had become everything I once mocked.
But here’s the thing—the jacket looked good. Not despite its dad-ness but somehow because of it. Paired with simple black jeans and minimalist sneakers rather than my father’s preferred pleated khakis and lawn-mowing shoes, it had transformed from embarrassing relic to fashion statement. I bought it immediately and have worn it three times since, receiving compliments each time.
The fashion industry’s endless cycle of irony and reappraisal has fully embraced what we once dismissed as “dad style.” The very aesthetic elements we ran from as teenagers—chunky sneakers, relaxed fits, practical outerwear, fanny packs (sorry, “belt bags”)—have been reclaimed, recontextualized, and frankly, improved. What was once the uniform of middle-aged suburban malaise is now the foundation of some of the most influential looks in contemporary menswear.
This isn’t just about fashion’s love of irony, though that’s certainly part of it. It’s also about a genuine reevaluation of what makes clothes good. The comfort and functionality that dads prioritized (while we were busy squeezing into skinny jeans that required lying down to zip up) actually make a lot of sense. Turns out the old guys might have been onto something with their roomy fits and practical pockets. They just needed some help with execution.
So let’s break down the dad trends worth reconsidering and how to wear them without looking like you’re actually headed to a neighborhood association meeting.
The dad shoe—specifically the chunky training sneaker—might be the most emblematic piece of this whole movement. What started with fashion insiders ironically embracing the aggressively normal New Balance 990s has evolved into a genuine appreciation for these supremely comfortable, deliberately unstylish kicks. The key difference between how they’re worn now versus how our dads wore them is all about context and proportion.
My neighbor Bob wears his gray New Balance 990s with relaxed-fit Dockers and tucked-in polos, creating a look that screams “I’m going to the hardware store.” When worn with cropped trousers, interesting socks, and a deliberately oversized sweatshirt or sharp jacket, those same shoes become a statement piece rather than a surrender to comfort. The contrast between the deliberately clunky footwear and more contemporary elements creates tension that reads as intentional rather than oblivious.
I resisted the dad shoe trend for years, clinging to my sleek minimal sneakers like they were the last vestige of youth. Then Trevor convinced me to try on a pair of 990v3s during a weekend shopping trip. The cloud-like comfort was immediately apparent, but what surprised me was catching my reflection and realizing they didn’t look half bad with my slim black jeans and unstructured blazer. They’ve since become my go-to travel shoes, carrying me through airport terminals with a comfort my Adidas Sambas never could. My father, when he noticed them during a recent visit, simply nodded and said, “Finally got sensible shoes, huh?” The satisfaction in his voice was unbearable.
Another dad staple experiencing a renaissance is the humble fleece. Once the uniform of nature documentary cameramen and suburban fathers at Saturday soccer games, the textured zip-up has been embraced by everyone from outdoor brands like Patagonia to high-fashion houses. The modern approach pairs these deeply practical layers with more unexpected elements—beneath a tailored overcoat, over a turtleneck with wide-leg trousers, or even with relaxed suit separates.
I acquired my first “fashion fleece” (words I never thought I’d type) last fall—a brick red number from a Japanese brand that cost approximately six times what my dad paid for his from Costco. When I wore it to brunch, layered over a white t-shirt with wide-leg twill pants and loafers, a stranger actually stopped me to ask where I got it. The satisfaction was immense, tempered only by the knowledge that my father has been wearing essentially the same item for decades without receiving a single compliment. Sometimes the only difference between “frumpy” and “fashionable” is the confidence of intentionality.
The fanny pack (or “belt bag” as marketers desperately try to rebrand it) represents perhaps the most surprising dad item comeback. Once the international symbol of the tourist father—worn exclusively at theme parks and while using a camcorder the size of a small microwave—these practical pouches have been reimagined by luxury brands and streetwear labels alike.
The contemporary approach wears them crossbody rather than at the waist, instantly transforming them from dorky to deliberate. The functionality remains identical (a place to store your wallet, phone, and keys without bulging pockets), but the execution feels completely different. I was skeptical until a three-day music festival convinced me of their undeniable practicality. Now I own two—a sleek black nylon version for everyday use and a more technical outdoor style for travel. My dad, who has worn essentially the same fanny pack to Disney World six times over three decades, finds this development hilarious. “Thirty dollars for that? Mine was eight bucks at Target!” he texted when I sent him a photo of my new acquisition. He’s not wrong, but he also tucks his t-shirts into his shorts, so we’re at an impasse.
Dad denim has also made a spectacular comeback, though with crucial updates. The light-wash, relaxed-fit jeans that dominated suburban malls in the ’90s have returned, but with more thoughtful proportions. Rather than the shapeless, pleated monstrosities that pooled around my father’s Rockports, today’s versions offer a relaxed straight leg with a higher rise and often a cropped length. Paired with loafers or boots rather than chunky white sneakers, and topped with something more interesting than a tucked-in polo, these jeans transform from sad to statement-making.
I’ve personally embraced a pair of faded vintage Levi’s 550s that would have looked right at home in my dad’s 1994 wardrobe. The difference is all in the styling—I wear them with everything from Chelsea boots and a black turtleneck to loafers and an unstructured blazer. The relaxed fit feels fresh after years of skinny jeans, and honestly, my lower body has never been more comfortable. The day I put them on and caught my reflection, I had the unsettling realization that I looked better in dad jeans at 35 than I did in spray-on skinny jeans at 25. Comfort and flattering don’t have to be mutually exclusive, a lesson my father apparently knew all along.
Perhaps the most unexpected dad trend revival is the return of the tucked-in t-shirt. This move, once the unmistakable hallmark of fathers at backyard barbecues nationwide, has been reclaimed by style-conscious men who recognize its power to create a cleaner silhouette. The modern approach pairs a simple, quality t-shirt (not the free one from your company picnic that your dad would wear) with higher-rise pants and often a statement belt.
I resisted this one for years, having spent my teenage years carefully cultivating the perfect untucked length for my t-shirts. The first time I experimentally tucked in a plain white tee with some wider-leg chinos and a vintage leather belt, my girlfriend stopped and stared. “That actually looks…really good?” she said, the surprise in her voice matching my own feelings. The proportions worked in a way I hadn’t expected, creating a cleaner line that made my casual outfit look intentional rather than lazy. When I visited home wearing this look, my dad actually pointed and laughed. “You made fun of me for that for twenty years!” His vindication was complete.
Even the practical outerwear that dominated dad closets has found new life. The fishing vest, once worn exclusively by actual fishermen and fathers who wanted sixteen pockets for unknown reasons, has been reinterpreted as a layering piece by brands from Japan to New York. The gore-tex hiking shell, formerly reserved for rainy trail excursions and coaching Little League in bad weather, now appears on runways and in streetwear collections.
I never thought I’d own a fishing vest that has never seen a fish, but here we are. Mine is navy canvas from a workwear brand, and worn over a sweatshirt with wide pants and boots, it somehow looks deliberately fashion-forward rather than like I took a wrong turn on the way to Bass Pro Shops. The multiple pockets are genuinely useful for city life (phone, wallet, headphones, notebook, pen, sunglasses), proving that sometimes dad practicality and style can peacefully coexist.
The baseball cap, long a dad staple (usually featuring a golf course logo or their favorite sports team), has been elevated from casual afterthought to considered accessory. Rather than the sweat-stained, curved-bill version my father would wear while grilling, today’s interpretation favors cleaner designs, more interesting fabrics, and a straighter brim. Worn with an otherwise polished outfit rather than as the finishing touch on full leisure wear, the cap becomes a deliberate style choice rather than a way to hide thinning hair.
My favorite cap is a simple navy wool version with no logo—miles away from my dad’s collection of various golf course caps with sweat rings around the band. But the function is identical—it adds a casual element to my outfit and requires zero thought about my hair. The wisdom of fathers, reinterpreted.
Even the sandal-with-socks combination, long the most ridiculed dad move in existence, has found redemption in fashion circles. Brands like Suicoke and Birkenstock have made the deliberately comfortable pairing acceptable, even desirable. The key difference is in the execution—think textured or patterned socks with sleek, minimal sandals rather than white tube socks with rubber slides.
I haven’t fully embraced this trend yet, though I’ve experimented with Birkenstock Bostons (technically a clog, not a sandal) worn with visible socks during transitional weather. Each time I do this, I feel my teenage self screaming in horror, but the comfort is undeniable, and when paired with otherwise considered pieces, it somehow works. My dad, who has been wearing socks with sandals to get the newspaper every Sunday morning for my entire life, deserves an apology I’m not yet ready to give him.
So what’s the secret to wearing these reclaimed dad pieces without looking like you’re actually chaperoning a middle school field trip? It comes down to three key principles:
First, it’s all about selective adoption rather than head-to-toe commitment. Wearing every dad trend simultaneously isn’t ironic or fashionable—it’s a costume. Choose one element—maybe the chunky sneakers or the fleece jacket—and pair it with more contemporary pieces. The contrast creates the tension that makes it work.
Second, proportion and fit remain crucial. Yes, silhouettes have relaxed, but there’s a massive difference between deliberately oversized and simply ill-fitting. Even the roomiest contemporary styles are cut with intention, with shoulders that hit in the right place and lengths that feel deliberate. Your dad’s clothes worked for him (sort of), but unless you share identical proportions, you need pieces cut for your body.
Finally, quality and materials elevate these formerly dismissed items. The technical fabrics, construction details, and thoughtful design of today’s “dad” pieces separate them from the bargain-bin 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 deliberately aesthetic.
The ultimate irony of the dad style resurrection is that most actual dads remain completely unaware that elements of their much-mocked wardrobes are now being sold at premium prices to their fashion-conscious sons. My father still wears essentially the same uniform he has for decades, blissfully unconcerned with the fact that his New Balance sneakers are now considered cool or that his practical outerwear choices have been vindicated by high fashion.
When I called to tell him that his style had finally become fashionable, he just chuckled and said, “So I can expect to see you at Thanksgiving in white sneakers, a fanny pack, and socks with sandals?” I told him not to push his luck. Some dad trends are still a bridge too far, at least for now. But given the rate of fashion’s rehabilitation of once-scorned items, I wouldn’t bet against eventually eating those words too.
The greatest lesson in all this might be that comfort and practicality—values dads have championed in clothing while their sons chased trends and suffered for style—aren’t inherently at odds with looking good. They just needed some refinement in execution. So next time you mock your father’s wardrobe choices, remember—in fifteen years, you might be spending good money to dress almost exactly like him. Just hopefully with better color choices than teal and purple.
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