Heritage, like a well-made garment, is fabricated. It is stitched carefully, starting with a single thread that interweaves with others to form a narrative. As that narrative fades, frays, and ages, the story changes, flexing and molding to fit whoever wears it.
Our closets are filled with such narratives—fragmented stories that, when assembled, articulate a personal sense of style. Think about a new piece of clothing as a blank page. Its story begins from the moment you clip the tag; ultimately, it is up to the wearer to imbue it with life and perspective.
But a piece of vintage clothing, an item with a heritage and narrative of its own, carries a different weight. How, then, do you wear someone else’s story?
For Chris Flynn, founder of Vintage Trouts, this question of heritage is not an abstract concept. It is his trade.
“Vintage Trouts started in 2023 as an homage to my father and my grandfather and the clothes that they wore,” Flynn says. “I just enjoy finding similar items and showing them to the community.”
From a young age, Chris noticed that his father and grandfather dressed with intention, opting for clothing that blended practicality and style. The items were rugged yet elegant, remnants of a time when men thought more about clothing’s purpose rather than just how it looked.
“These guys, whether they knew it or not, were throwing fits,” Chris told me with a chuckle. “I would look at these old pictures of my father on the river with my grandfather, and it wasn’t so much that they were just fashionable—they were functional. They wore equipment that lasted.”
Today, most affordable menswear may be suitable for the office, a night out, or relaxing on the weekend, but it lacks the craftsmanship to withstand activities like manual labor or time outdoors. Above all else, Chris believes functionality places vintage finds a cut above their modern contemporaries.
“I still have an L.L. Bean vest that my dad owned,” Chris said. “It’s over forty years old and is still in great condition.”
A lifelong angler and fashion connoisseur, Chris started to marry his beloved hobbies during the pandemic, when hours of isolation and boredom provided time to fish or troll the internet for vintage clothing and gear.
“I’m always looking for stuff that I like, whether it’s art pieces, a hat, a vest, or a jacket,” Chris told me. “For the most part, I’m still sourcing most of our finds online through Depop and eBay.”
As Chris fell deeper down the rabbit hole, he slowly built an impressive personal collection: hats and jackets, packs and vests, rods, reels, books, and flies. Despite drowning in an ocean of inventory, Chris had no intention of turning his obsession into a business. To him, it was a welcome way to stave off boredom. Nothing more.
That all changed when Chris’s father passed away in 2020.
Suddenly, the clothing his father left behind took on new meaning. Chris realized that vintage finds are compelling not only because of their craftsmanship or scarcity, but because of the memories they hold.
“I don’t really remember the things that my dad bought for me through the years. I remember the things that we did together,” Chris said. “I feel like in these times of mass consumption and over-consumption, people are really looking for ways to connect with items on a different level.”
In honor of his dad and the clothing he loved, Chris founded Vintage Trouts in 2023. At first, he started small, selling vintage trout and fly-fishing brand patches on hats. But once demand increased, Chris expanded into clothing. To this day, Chris gives credit for his early success entirely to his trusted business partner: his wife.
“I work a full-time job, so Vintage Trouts is still very much a side hustle,” Chris said. “I really couldn’t have done any of this without my wife. It’s not an uncommon sight to see her and me packing up orders while our son is crawling between the boxes—just total madness.”
Just as it began, family remains a core motivator of Vintage Trouts. Together, Chris and his wife have amassed over thirty thousand followers on Instagram, provided clothing for branded photoshoots, and even run a pop-up in Filson’s Broadway store in New York City. Nevertheless, Chris hasn’t compromised on the meticulous curation of his finds.
“With stuff from the ‘80s and ‘90s, you can see where the quality cut-off was,” Chris said. “If I’m sourcing a canvas shirt from that era, the main tag I look for is ‘Made in the U.S.A.’ That was the first thing I learned: not all vintage is created equal.”
As Vintage Trouts continues to gain traction, Chris has his eye on the future. He hopes to expand beyond vintage gear while keeping his primary focus on community and getting people excited about the outdoors.
“It’s always been about getting people interested in fly fishing,” Chris said. “If I have a decent-sized menswear contingent and this gets them interested in being outside, enjoying nature, and becoming conservators of the sport, that’s a win.”
Chris is hopeful that Vintage Trouts can eventually become his full-time profession—a passion that not only fills his cup but pays the bills. Still, he will always be drawn to the clothing, its stories, and the people who connect with his finds.
“When we did our pop-up at Filson back in 2024, I had one of the old Filson fishing vests there,” Chris told me. “A lady comes in, sees the vest, and literally starts tearing up. Her husband, who had retired, had that exact vest and lost it somewhere on a trip, and she was buying this one for him for Christmas. I was honestly so fulfilled by that. My favorite find and sell of all time was that Filson vest—it’s really hard to top that.”
If you are interested in learning more about Vintage Trouts, check out their website,
and Outpost’s own curated collection.
