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Bibliophile Style: Ernest Hemingway – Habilitate

maximios June 19, 2025 Fashion

Image credit: U.S. National Archives and Records Administration / Public domain

Today marks the arrival of a long-awaited PBS documentary by Ken Burns and Lynn Novick about Ernest Hemingway. The three-part series is timed to coincide, somewhat macabrely, with the sixtieth anniversary of his death. While Hemmingway is one of the most talked-about and oft-photographed authors ever to commit print to paper, it’s easy to see why he continues to be an appealing subject for biographers in any medium. His life — coloured as it was by battlefields, corridas, safaris and the like — alongside his outsized reputation as one of the most influential authors of the previous century, means that Hemingway has long been more myth than man. So picking apart his complex legacy is an enticing prospect. And, with ample archival imagery documenting his storied career, there’s also the not incidental matter of his wardrobe to consider.

Having looked recently at F. Scott Fitzgerald’s clothes, Hemingway seems like the obvious next writerly candidate to consider. Not only were Scott and Ernest longtime friends and literary rivals, their wardrobes are perfect sartorial analogues to their respective authorial approaches. 

Fitzgerald’s urbane three-piece suits and up-to-the-minute fashion sense mirrored his lively and original recreations of the 1920s. Not only did he literally define the Jazz Age (he coined the phrase), his writing proved novel in both style and content. The Great Gatsby, for example, contains one of the first car accidents in literature, automobile ownership having only recently become a more commonplace phenomenon. 

Hemingway’s writing style and subject matter were no less innovative, and arguably even more so. His famously terse and minimal prose proved revolutionary, making him perhaps the most widely imitated author of the last hundred years. He also tackled themes that the literature of a war-ravaged century could no longer ignore, including bloodshed, betrayal, and death. But compared to Fitzgerald, his approach to writing was considerably more muscular, carved out of short sentences and terse monosyllables.

Image credits: John F. Kennedy Presidential Library / Public domain; John F. Kennedy Presidential Library / Public domain; John F. Kennedy Presidential Library / Public domain; ; John F. Kennedy Presidential Library / Public domain

The macho minimalism of his prose was equally applied to his clothes. Hemingway largely eschewed Fitzgerald’s urbanity for a wardrobe composed overwhelmingly of ‘manly’ signatures. He was particularly known to don the garms of his many and varied manly pursuits. Hunting, fishing, boxing, bullfighting, drinking — you name it, Hemingway got the proverbial T-shirt. Accordingly, he regularly wore Aran sweaters, safari jackets, hunting vests, high boots, and Viyella shirts — that is, when he wore shirts at all. If photographs are anything to go by, much of his later days appear to have been spent persistently bare-chested. (Remarkably, when so many images from his final years seem to depict a grey and grizzled old man, he was just 61 when he died).

Image credits: John F. Kennedy Presidential Library / Public domain; John F. Kennedy Presidential Library / Public domain; Eleanor Jaekel / Public domain; John F. Kennedy Presidential Library / Public domain

Along with fellow outdoorsmen Teddy Roosevelt and Charles Lindbergh, Hemingway was an early ambassador for the adventure brand Willis and Geiger in the early 1900s, and apparently even had a hand in designing one of their bush jackets. He was also an early Abercrombie and Fitch customer. Back before they had pivoted to prep, the brand once sold the kind of outdoorsy getup that was right up Hemingway’s street. While living in Cuba, he reportedly got a giant consignment of goods from the retailer, undeterred by the hefty duties imposed on American goods. 

Then there’s the facial hair. Barely ever clean-shaven, much of Hemingway’s earlier years saw him sporting a moustache, while in later decades he typically went full sea captain. His combination of bushy beard and adventurer get-up has likely inspired as many hipsters and ‘lumbersexuals’ to sprout facial hair and buy utility vests as his prose has cut short the scribblings of aspiring writers. I can attest to having personally tried and failed to pull off the same, with both beards and brevity proving a perpetually bad fit.

Image credit: The U.S. National Archives / No known copyright restrictions

It’s worth noting though that the oft-cited search for authenticity that underpins the menswear community’s love of the workwear of yesteryear was also at play in Hemingway’s day. While it’s easy to hold up Papa as the grandad of manly style, he too was dressing in search of a foregone masculine ideal. As Brenden Gallagher writes:

While Roosevelt and Hemingway are remembered as outdoorsmen and adventurers, they modelled 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 pickaxe 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 complement 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.

Brenden Gallagher

Image credit: Yousuf Karsh / Public domain

Looking at photos of Hemingway, his desire to conjure or live up to some masculine ideal seems evident at times. It shines through in the details of clothing choices that seem too calculated even on him. I think you can spot it occasionally in the berets, the Breton tops, and the fringed vests. Or in the way a particular hat might be cocked or the combover he adopted in middle age. This was not a man whose wardrobe was simply a reflection of the practical demands of an active lifestyle. Rather, like all of us, he was in some part touched by vanity and a desire to project an image.

Image credit: John F. Kennedy Presidential Library / Public domain; John F. Kennedy Presidential Library / Public domain; U.S. National Archives and Records Administration / Public domain; Hans Malmberg / Public domain

Jay Fielden, in a great piece written for the Wall Street Journal in anticipation of the new PBS series, notes the following about the writer reaching the end of his life:

By then, he’d played the bearded macho-man armed with a gun and a typewriter — spoiling for danger, tough women and a stiff drink — for so long that the caricature stuck. The masculine stereotype continues to complicate our ability to see the person lost inside the testosterone legend, much less to extricate the writing from the writer. So numerous are the photographs of Hemingway on safari, at the corrida, charming his next wife, hooking a big one, behind the typewriter — almost always shirtless — that the visual lore has become intermingled with scenes from his novels and journalism in a way that makes it hard to recall what’s fact or fiction

Jay Fielden

Such murky mythologising is equally true of Hemingway’s clothes. In some parts bona fide, in others contrived, they continue to speak to us from the past with the same rugged endurance as his persona and his prose.

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