The way Hemingway lived his public life echoed his prose by design. He was a war reporter and an outdoorsman. He ran with the bulls, safaried in Africa, and enjoyed boxing and bourbon in equal measure. He wasn’t necessarily playing a role, but he did seek out a life that would externalize his prose. He carefully curated his personal mythology through fashion. Safari jackets, viyella shirts, high boots, thick wool sweaters, and sheepskin vests were all in regular rotation in his wardrobe. He set out to build a mythology around himself as deep as his oeuvre. Shifting his look from rum soaked ex-pat to post-colonial explorer to beleaguered longshoreman, the goal was always masculinity perfectly distilled. And it worked. Even now, more than fifty years after his death, Hemingway’s style is still a cornerstone of a particular tradition of rugged, intellectual menswear. His sartorial/ imprint is ubiquitous: from the pages of L.L.Bean to hip menswear boutiques with names like Antler & Arrow: Papa’s menswear legacy lives on. You can even purchase apparel from the Ernest Hemingway collection if you want to make sure you get the look just right.

For the same reasons that Hemingway’s work and biography still resonate today, his style continues to have an impact on new generations of men. Men read his books and desire to run with the bulls, drive war zone ambulances, and catch the big-ass fish of their forefathers. Then they look to the the adventurous men of previous generation and see the same safari jackets and cable knit sweaters, because they too once had the same sartorial urges. Then, a new generation buys deer skin vests and work-worn boots, even if those clothes aren’t meant for adventuring further than Bushwick.

In fact, this impulse to dress like an extinct breed of “real men” extends back further than Hemingway himself. Gold miners, arctic explorers, and jungle cartographers of the 19th century and earlier wore what was comfortable for their terrain: there was no “outdoorsman” look that united the various and sundry frontiers that were being traversed at any given time. You certainly couldn’t buy the look of a mountaineer on Fifth Avenue. Fashion both before and during the era of Jack London wasn’t so much focused on the cut of their sheepskin vest, but whether or not it kept a man warm. As we look at fashion’s more ostentatious and experiemental sides, it’s important to note that this is a time and demographic whose interests were purely functional, not fashionable. Some of these adventurers came back and realized that that men not only admired them, they wanted to be them. They also didn’t want to have to go all the way to Mt. McKinley or Kilimanjaro to do it. At the dawn of the 20th century, there was no such thing as an “expedition brand,” and twenty years later, the “outdoorsy” look had changed fashion forever.

Brands like Willis and Geiger emerged in the early 1900s for the dual purpose of selling the look of the outdoorsman to cosmopolitans and outfitting the next generation of adventurers. Quickly, the idea of selling the look of expeditions and safaris to average joes started gaining traction. To build their brand, Willis and Geiger sought out Teddy Roosevelt, Charles Lindbergh and, of course, Ernest Hemingway as brand ambassadors. Quickly, they started selling their clothes to L.L. Bean, Abercrombie and Fitch, and Eddie Bauer. Eventually, the brand gained wholesale clients, including aviation gear. Though they started off as a facsimile of what adventurers wore, this gave them an air of authenticity, making them all the more legitimate in the eyes of their consumers. Convincing the Hemingways and Roosevelts of the world to wear their clothes was a part of that.

Willis and Geiger weren’t the only brand to follow this playbook. In a noted biography of Hemingway, there is a report of him receiving a massive order from Abercrombie and Fitch in Cuba, despite the hefty duty at the time. Though we know them as a failing preppy retail brand today, Abercrombie began its life selling the outdoorsy look to the sedentary masses. The brand and Hemingway had a symbiotic relationship. A man like Hemingway would wear clothes like Abercrombie’s, bolstering the reputation of both.

While Roosevelt and Hemingway are remembered as outdoorsmen and adventurers, they modeled their look and their exploits on an earlier generation of man. It is important to remember that while Roosevelt charged San Juan Hill and Hemingway boxed his way through Cuba, these men were born with relative silver spoons in their mouths. Hemingway hailed from the comfort of suburban Chicago and Roosevelt was an American aristocrat. They weren’t exactly forced to survive in the mountains with nothing but a pick axe and a dream; they were the hipster trust fund kids and Vice video bloggers of the day. And they had a similarly outsized influence on men’s fashion. History fogs the reality that they were not far off from hipsters who cultivate a beard to compliment their Redwing boots and vintage bomber jacket. When we strive to dress like Hemingway today, we are chasing the same masculine myth that Hemingway pursued when he started first to dress like...well, Hemingway.

After Willis and Geiger filtered their clothing into stores like L.L. Bean and Eddie Bauer, this style became enmeshed with menswear DNA. These brands saw that when their clothes told a story about masculinity, about a sense of manhood that was slipping away, sales soared. Since then, these outdoor clothes have sold the same dream that was already beginning to dim decades ago: refusing to believe that everything there is to be discovered has already been found. We could fill pages with brands that have followed the same playbook to massive success: from Land’s End to Patagonia, from Pendleton to Orvis.

This idea persists today. Whether you call it “urban rustic,” “lumbersexual,” or “blue collar chic,” the 2010s saw a rebirth of this same style sensibility, perhaps in response to accusations that upwardly mobile urbanites were becoming “metrosexuals,” a modernized version of the accusation of “fop” or “dandy.” Suddenly, a new generation looked to the Hemingway school of style to reaffirm their sense of masculinity. You don’t have to look hard to find a menswear shop that evokes Hemingway, either directly or by association. When you walk into a shop with leather bound books, vintage luggage, taxidermy, or aging nautical detritus as decor, they are nodding to Hemingway.

Whether we’re talking about the rise of the “rhinestone cowboy” in the ‘70s or the “lumberseuxal” phenomenon of recent years, the impetus is the same. The urban man feels claustrophobic. They think about what it is they might discover. For millennials, these thoughts have manifested themselves in the form of taxidermy, artisanal cocktails, and vintage flannels. Who can forget that moment when artisanal axes became a sartorial accessorial for a brief, strange pioneering moment?

Like generations before them, this moment also meant reaching for Hemingway, and trying to figure out what frontiers, if any, were still available for exploration. It isn’t quite fair to say that Hemingway and his fashion descendents are selling something that doesn’t exist. Rather, Hemingway and the explorer style associated with him is grasping for something primal, masculine, and authentic. Maybe this clothing is a costume for a world that doesn’t exist anymore, but maybe there is a chance that there are things yet to be discovered.

Oh, and it’s safe to say that whoever discovers the next frontier will probably have read some Hemingway.