Last month I found myself in this pretentious menswear store in SoHo—you know the type, concrete floors, exactly three shirts on display, salespeople dressed like Victorian undertakers. I was there interviewing the founder for a feature, and he kept throwing around the phrase “American heritage” like he was personally responsible for preserving national treasures. At one point, he actually said with a straight face: “Our $395 selvedge denim is inspired by the authentic spirit of the American frontier.” I nearly choked on my complimentary sparkling water. The guy was from Connecticut and had launched his brand in 2018.
Don’t get me wrong—I love American style classics as much as the next menswear nerd. Hell, probably more, considering I have an entire storage unit filled with vintage workwear that my ex-girlfriend used to call “the museum of things that smell like other people’s grandpas.” But there’s something that drives me absolutely nuts about how the term “American classic” gets thrown around these days. It’s become less about historical accuracy and more about creating convenient myths that sell $300 T-shirts.
Here’s the thing about true American style classics—they weren’t created to be classics. They were created to solve specific problems, usually by people who were too busy working to care about looking “authentic.” Take the Levi’s 501. We now treat it like some sacred text of American design, but it started as literal work clothes for miners and ranch hands. They weren’t trying to create an icon; they were trying to make pants that wouldn’t fall apart when you were, you know, mining for gold. Function first, fashion nowhere on the priority list.
My grandfather worked at a steel mill in Pennsylvania for 38 years. I once showed him an “authentic reproduction work shirt” I’d bought for an embarrassing amount of money, and he laughed until he started coughing. “We would’ve set fire to something that stiff,” he said. “Couldn’t move your arms properly.” Heritage brands love to talk about the “honest workers” who inspired their collections, but actual working people prioritized comfort and durability over some romantic notion of rugged authenticity.
The marketing mythology around American classics gets especially weird when brands start inventing histories that never existed. I was at a trade show in Las Vegas last year when a brand rep cornered me to tell me about their “historically accurate reproduction” of a military jacket from 1943. I happen to collect vintage military gear (I know, I’m a walking cliché), so I asked some specific questions about the original specs. The guy couldn’t answer any of them. Later, I discovered the design they were “reproducing” never actually existed—they’d combined elements from several different eras and invented a backstory. That’s not heritage; that’s historical fan fiction.
But here’s where it gets complicated. Some American classics genuinely deserve their status—they really did change how people dressed and have remained relevant for decades. The white t-shirt, for example. Originally an undergarment for Navy sailors around 1913, it emerged as outerwear during WWII, got the James Dean treatment in the 50s, and has never left the cultural conversation. Or the aviator sunglasses, which were literally designed for pilots in the 1930s but still look great today. These are the real deal—designs that have proven their staying power across generations without much modification.
My buddy Marcus makes an important distinction that I’ve adopted: “Is it a classic because it’s good, or is it ‘good’ because someone says it’s a classic?” Lots of stuff falls into that second category. The penny loafer gets talked about as this eternal American staple, but it’s been in and out of fashion dozens of times. Same with the button-down oxford shirt. These aren’t bad items—they’re great, actually—but their “classic” status has been carefully managed and marketed over decades.
The marketing of American classics often relies on selective history. Brands love to talk about how their khakis were worn by WWII officers but conveniently forget that the design originated as colonial British military uniforms in India. Or they’ll wax poetic about the rugged individualism of the cowboy boot while glossing over its mixed Spanish, Mexican, and Native American influences. American style is actually at its best when it’s honest about being a melting pot of influences, just like the country itself.
I ran into this friction firsthand when researching an article about the history of the leather jacket. A major American brand had built their entire marketing story around being “the original,” with ads suggesting their founder basically invented the concept in the 1920s. When I dug into actual historical records and vintage examples, it became clear that leather jackets had been evolving across multiple countries simultaneously, with key innovations coming from military contractors, motorcycle companies, and European designers. When I included this in my article, the brand pulled their advertising from our website for three months. Apparently, historical accuracy was less important than their founding myth.
What’s especially funny is how many “all-American classics” aren’t remotely American in origin. The desert boot? British design inspired by shoes worn in Egypt. The field jacket? Variations exist from military traditions worldwide. Denim itself? The fabric originated in Nîmes, France (hence “de Nîmes” becoming “denim”). But marketing departments can’t sell “multinational design traditions thoughtfully adapted for American use”—not as catchy as “BORN IN THE USA!” plastered over a filtered image of some model pretending to chop wood.
The price inflation that comes with this mythmaking is what really gets under my skin. Last week I watched a guy in Brooklyn pay $985 for a “heritage-quality” reproduction of a canvas work jacket that I found the actual 1950s version of at a thrift store in Ohio for $15. The reproduction was beautiful, sure—perfect stitching, historically accurate pattern, artisanal whatever. But paying luxury car money for a simulated working-class garment feels… I don’t know, weird? Maybe I’m overthinking it.
Then again, I own a painfully expensive reproduction of a World War II flight jacket, so maybe I’m part of the problem. I justified it by telling myself it was better constructed than anything I could find vintage in my size. That might be true, but I also just wanted it, which is probably the more honest answer. We all have our hypocrisies, especially in how we approach style. I’ve made peace with mine, mostly.
My friend David, who works as a vintage dealer in Chicago, has a theory I find compelling. He believes the obsession with American classics actually intensified as American manufacturing declined. “It’s nostalgia for something we’re actively destroying,” he told me over beers last time I was in town. “We shut down the factories, moved production overseas, and then fetishize the products those factories used to make.” There’s something perverse about a $400 “American heritage workwear” shirt made in a factory with questionable labor practices on another continent. But that’s the reality behind a lot of what gets marketed as classic Americana.
Of course, there are exceptions—brands that are genuinely committed to both historical accuracy and ethical modern production. They tend to be smaller, more specialized, and refreshingly straightforward about what they’re doing. I visited a workshop in Portland last year where they’re making bags using machines and techniques from the 1940s. No fake backstory, no sepia-toned marketing—just people who love traditional craftsmanship keeping it alive. That feels different from the corporate heritage cosplay that dominates the market.
It’s easy to become cynical about all this, but I try to remember that every generation reinvents tradition in its own image. The “authentic” Americana workwear obsessives of the 2010s weren’t actually more authentic than today’s reinterpretations. And the original makers weren’t thinking about authenticity at all—they were just solving problems with the technology and materials available to them at the time. Maybe authenticity is a weird standard to apply to clothing in the first place.
I had dinner with my dad last time I was home in Chicago, and he pointed to my jacket—a reproduction of a 1950s style—and asked if it was vintage. When I explained it was new but based on an old design, he looked genuinely confused. “So it’s a costume?” he asked. I started to explain about heritage design and historical references, but halfway through my explanation, I realized I sounded ridiculous. From his perspective, there was vintage clothing (old stuff) and modern clothing (new stuff). This middle category of new things pretending to be old things didn’t make sense to him. And maybe he had a point.
There’s a store in Manhattan that sells $300 reproductions of jerseys from Negro League baseball teams of the 1930s. The craftsmanship is impressive, and the designs are beautiful. But when I interviewed the founder for a piece last year, I asked how much of their profit goes to the families of the original players or to supporting causes related to the Negro Leagues’ history. There was an awkward pause followed by some corporate doublespeak about “raising awareness.” This is the dark side of the American classics industry—borrowing cultural equity without giving anything back.
So what’s the alternative? I’m not suggesting we can or should only wear actual vintage clothing (though that would certainly be better for the planet). And I do believe there’s value in keeping traditional designs and techniques alive. I guess I just wish there was more honesty in how these products are marketed. Don’t tell me your five-year-old brand is “authentic American heritage” when your founder worked at Goldman Sachs until 2018. Don’t charge heritage prices without heritage quality. And maybe acknowledge that American style, at its best, has always been about adaptation and evolution rather than preserving some mythical golden age.
The most genuinely “classic” American garment I own is probably my dad’s Carhartt chore coat from the 1980s. It’s beaten to hell, patched in three places, and the corduroy collar is worn smooth from four decades of wear. He never thought of it as a style statement—it was just the coat he wore to do yard work. But every time I visit home, I notice how young guys in his neighborhood are now wearing new versions of the exact same coat, carefully distressed to look like they’ve done a hard day’s work when they’ve actually just been to Starbucks. Dad finds this hilarious. “They’re paying to look like they can’t afford a new coat,” he says.
Maybe that’s what I find so funny about the whole “American classics” market. The original versions of these garments were usually designed to be affordable, practical options for people who needed durable clothes for hard living. Now we’ve transformed them into luxury goods, status symbols that signal how much you know about the history of clothes most people used to wear because they couldn’t afford anything fancier.
The irony is delicious, even as I participate in it myself. I’m not above the contradiction—I just think we should acknowledge it. There’s nothing wrong with appreciating well-designed classics or even paying for quality reproductions. Where it gets weird is when we start inventing mythologies to justify our purchases or pretending that buying expensive versions of workwear somehow connects us to an authenticity we’re otherwise missing.
The next time a brand tries to sell you on their authentic American heritage, maybe ask a few questions. When were they founded? Where are their products actually made? What problem was the original design trying to solve? And most importantly, does the product stand on its own merits without the mythology? The true classics always do—no origin story required.
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