I’ll never forget the look on Vincent’s face – my old boss at American Style magazine, the guy who once fired me for soaking a Tom Ford shirt with an industrial steamer. He was visiting New York from his new gig in Milan, and we’d met for drinks at this pretentious rooftop bar where everyone was dressed like they were auditioning for a fragrance commercial. I showed up wearing what had become my standard summer uniform: shorts (nicely tailored, thank you), a linen shirt (ironed, mostly), and – this is where Vincent nearly choked on his negroni – a fishing vest.
Not a fashiony “inspired by” fishing vest. An actual fishing vest. The kind with multiple pockets and little loops for tools and a mesh back for ventilation.
I’d bought it at a sporting goods store for $42 during a weekend trip to Maine three months earlier, and it had unexpectedly become the most practical piece of clothing I’d ever owned. “Jackson,” Vincent said, placing his drink down carefully like he was afraid sudden movements might encourage my poor fashion choices, “what in God’s name are you wearing?” That fishing vest is now four years old.
I own three of them in different colours.
And I’m far from alone in embracing what fashion circles initially dismissed as an “ugly” trend but has since gained serious traction for its sheer practicality: technical outdoor gear worn in decidedly non-outdoor urban settings. I’m talking about fishing vests, hiking sandals, trail runners worn with jeans, waterproof crossbody bags, cargo trousers with actual functional pockets, and other pieces once exclusively associated with national parks or, worse, tourists. These items were fashion punchlines for years – the punchiest of which was the classic “Dad on holiday” look complete with a fanny pack, zip-off trousers, and bucket hat (all of which, I should note, are now seen on cool kids in SoHo).
The rise of these “ugly” but practical items represents something important in American menswear: a shift toward valuing functionality over arbitrary aesthetic rules. It’s perhaps the most honest trend we’ve seen in decades, born not from designer runways or celebrity influence but from the simple realization that sometimes the uncool solution is actually the right one. Take my beloved fishing vest.
It solves a problem most men constantly face: where to put all our stuff. In an age of ever-larger phones, wallets stuffed with cards, keys, AirPods, sunglasses, and now masks, our trousers pockets have become overstuffed disaster zones that ruin the lines of otherwise decent outfits. The standard solution – cramming everything into bulging pockets – is both uncomfortable and unflattering.
The fishing vest distributes the load across multiple specialised pockets without the sweaty back issue that comes with backpacks. It’s genuinely brilliant design. I first noticed this trend gaining legitimacy around 2019, when I was covering a trade show in Portland.
Half the stylish guys there were wearing some version of technical hiking shoes with otherwise normal urban outfits. Not the fashion version from designer collaborations, but actual trail runners from Salomon, Hoka, and other authentic outdoor brands. These shoes were designed for mountain paths but were being adopted for city pavements because – surprise – features that make a shoe comfortable and supportive on rugged terrain also make it comfortable for walking twenty blocks in Manhattan.
My friend David, the photographer who’s always ahead of trends, had been wearing Salomon trail runners for years before they caught on. “People used to ask if I was going hiking after our shoots,” he told me recently. “Now they ask where I got my shoes.
Nothing about them changed except perception.” He’s right. The shoes didn’t change – our willingness to prioritise comfort and function over arbitrary style rules did. This shift isn’t just some fleeting trend.
It represents a significant evolution in how American men approach getting dressed. For generations, men’s fashion has operated under a bizarre assumption that looking good should involve some level of discomfort or inconvenience. Dress shoes with leather soles that slip on wet pavements.
Suits that restrict movement. Trousers with pockets too small to hold a modern phone. We accepted these limitations as the cost of “dressing well.” The outdoor-urban fusion rejects this premise entirely.
It asks: Why can’t clothes be both functional AND look good? Why suffer through inadequate pockets when cargo trousers exist? Why wobble on slick dress shoe soles when Vibram exists?
This approach feels uniquely American in its pragmatism – a country built on practical innovation finally applying that mindset to how we dress. I’ve watched this evolution play out in real-time through my dad’s wardrobe. For years, I’d try to get him to “upgrade” his style when he visited New York, quietly embarrassed by his ultra-practical clothing choices.
I once spent three hours helping him shop for “better” shoes to replace his chunky New Balance trainers, only to have him donate the new shoes after one uncomfortable day of city walking and revert to his trusty NB’s. Now those same New Balance dad shoes are considered stylish, and I’ve eaten enough crow to feed a family of four. “You finally caught up,” he said smugly on his last visit, pointing to my own pair of deliberately chunky trainers.
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He wasn’t wrong. The tipping point came when legitimate fashion brands began not just referencing outdoor gear but directly collaborating with technical outdoor companies. Suddenly Salomon wasn’t just making shoes for actual trail use; they were doing limited releases with high-end boutiques.
Arc’teryx wasn’t just equipping mountain climbers; they were a fashion week staple. The North Face wasn’t just for ski trips; they were collaborating with Gucci. The wall between “technical outdoor gear” and “acceptable urban fashion” had been permanently breached.
And thank god for that. Because when something works really well at its intended function, it often contains a kind of honest beauty that purely decorative items can’t match. There’s a reason military and workwear designs have influenced fashion for decades – they’re created to solve specific problems, and that purpose-driven design often results in pieces that look authentically cool in a way that purely aesthetic designs sometimes miss.
The fishing vest isn’t beautiful in a conventional sense. Neither are cargo trousers or hiking sandals or chunky trail runners. But they possess something more interesting than conventional beauty: they’re genuinely useful.
They make life easier. They solve problems. And in a world with enough problems already, anything that makes daily existence slightly more convenient deserves serious consideration, regardless of whether it fits into arbitrary notions of what looks “sophisticated.” I now regularly recommend technical outdoor pieces to guys looking to upgrade their everyday wardrobes, especially those who live in cities and need clothes that can handle commuting, unpredictable weather, and carrying all the gear modern life requires.
The key is balance – pairing these highly functional items with otherwise normal clothes to avoid looking like you’re about to summit Everest during your coffee run. My standard approach: One technical piece per outfit. A fishing vest over a simple button-down and chinos.
Trail runners with regular jeans and a jumper. A technical waterproof bag with an otherwise classic outfit. This keeps the look grounded while still benefiting from the practical advantages these pieces provide.
The brands getting this balance right are worth noting. Some, like Snow Peak from Japan, bring a minimalist design sensibility to outdoor gear, creating pieces that work as well in urban settings as they do in nature. Others, like Patagonia, have always maintained high design standards alongside technical performance, making their crossing into fashion territory feel natural rather than forced.
I’m not advocating for everyone to start dressing like they’re starring in an outdoor catalogue, to be clear. But I am suggesting that rejecting functional items solely because they don’t fit traditional notions of what looks “stylish” is a dated mindset that ignores the realities of modern life. American men’s style is evolving toward a more practical, comfortable reality, and that’s something worth celebrating.
This evolution also reflects broader cultural shifts in how we define masculinity and status. Traditional men’s fashion has long been tied to rigid professional dress codes and displays of conventional success. The embrace of outdoor-inspired gear represents a more fluid approach to identity – one where a man can signal priorities beyond just conforming to office expectations or flaunting wealth through recognizable luxury brands.
Vincent eventually came around on my fishing vest, by the way. After mocking it through two drinks, he reluctantly admitted it “wasn’t terrible” by our third round. By the end of the night, he’d made me list every pocket and its contents, fascinated by how effectively it had solved my storage issues.
Six months later, he texted me a selfie from Milan wearing what he described as a “sophisticated urban utility garment” but was quite clearly a fishing vest with the logo removed. I sent back a single fishing emoji.
He did not appreciate my humour.
Look, I’m not claiming the fishing vest is going to replace the sport coat anytime soon. But I am suggesting that the line between “ugly but practical” and “legitimately stylish” continues to blur in interesting, productive ways. As American men, we’re fortunate to be dressing during a time when comfort and functionality are increasingly recognised as valid priorities rather than admissions of defeat.
So the next time you find yourself dismissing something as too “ugly” or practical to be stylish, ask yourself: Does it solve a real problem? Does it make life easier? Does it actually work well?
If the answer is yes, it might be worth reconsidering. After all, there’s nothing more uncomfortable than uncomfortable clothes, and there’s nothing less stylish than being distracted by your own discomfort all day. As for me and my fishing vest?
We’ll be over here, carrying everything comfortably, staying cool in the summer heat, and no longer caring who thinks it’s a fashion faux pas. My dad was right all along – sometimes the practical choice is the right choice, whether fashion people get it yet or not.
