As a lawyer, I have often admired and tried to replicate Ernest Hemingway’s minimalist, “Iceberg Theory” style of prose. In fact, as a law clerk, I was asked what I read for fun. I said nonfiction, get rich quick, self help, religion, philosophy, etc., voraciously. I was told, “read Hemingway, you could learn to write from him” as the senior partner was alluding to his flat, sparse prose style.
However, something not to many look into with the proper retrospection—his clothing style is also worth taking a serious look into replicating. Ernest Hemingway built his literary reputation on restraint. His prose is famously lean, direct, and free of unnecessary ornamentation. Every sentence serves a purpose, proving that simplicity can possess extraordinary power. He applied much the same philosophy to his personal style. Choose pieces with clean lines and timeless design rather than excessive embellishment. As Hemingway understood, what you leave out can be just as important as what you include. His closest friends and companions included F. Scott Fitzgerald, his most famous literary friendship. Though they had a famously competitive and complex dynamic, Hemingway frequently critiqued Fitzgerald’s work and chronicled their wild Paris years together in A Moveable Feast and James Joyce, as the two were prominent drinking buddies in 1920s Paris. The soft-spoken Joyce frequently relied on Hemingway’s physical prowess to deal with barroom brawls. Joyce and Fitzgerald are among my favorite authors.
Classics endure because they transcend fashion, and few American writers have proven more enduring than Ernest Hemingway. His novels continue to be read, studied, and rediscovered by each new generation, earning him a permanent place in literary history.
The same can be said for truly exceptional jewelry. While trends come and go, diamonds, pearls, and finely crafted precious metals never lose their appeal. These are the foundation pieces of a well-curated collection—versatile enough for everyday elegance and refined enough for life’s most memorable occasions. Like Hemingway’s greatest works, they remain relevant because true style is never dictated by the season.
Hemingway lived as boldly as he wrote. Whether serving in World War I, fishing the Keys, or hunting on safari in East Africa, he cultivated a life defined by adventure, resilience, and quiet confidence. Those experiences shaped not only his writing but also his unmistakable sense of personal style.
Hemingway as a rugged, utilitarian man who rarely wore traditional jewelry but possessed notable timepieces and cherished personal talismans. His personal collection and notable items include: Rolex Oyster Perpetual: Hemingway famously owned and wore a Rolex, and he even wrote about the brand in his 1950 novel Across the River and into the Trees. L. Leroy & Cie. Pocket Watch: On his wedding day in 1946, Hemingway received an 18k gold open face pocket watch from his friend Charles C. Ritz (owner of the Ritz Hotel in Paris). He used this watch heavily to time horse races. Lucky Chestnut: Beyond metal accessories, Hemingway reportedly carried a “lucky chestnut” in his pocket for 11 years, which later became an item of great personal provenance kept by his friends. Personal Effects at Finca Vigía: Closets at his former home in Cuba (the Finca Vigía) famously contain additional clothing and personal memorabilia. That spirit translates beautifully to jewelry. Don’t be confined by traditional ideas of masculine or feminine design. Bold signet rings, substantial cuffs, leather accents, and architectural metalwork all carry a sense of strength that complements both men’s and women’s wardrobes. The most compelling jewelry reflects character rather than convention. Hemingway reminds us that authentic style is built on confidence, and confidence never goes out of fashion.
Hemingway treated fishing much like his writing schedule. He strictly wrote in the early hours (usually from 7 AM until noon) and spent his afternoons on the water, viewing fishing not as a hobby, but as a major passion. Some say drinking was his other major passion and that it was the bars that he spent his afternoons in drinking. Hemingway spent his afternoons at El Floridita Bar, drinking custom double-rum daiquiris (the “Papa Doble.”)
My friend Brian over at Woodcock & Co., is a Hemingway style afficianado and he is working on an upcoming book about the same. He went so far as to re-create Hemingway’s famous leather vest. The vest represents far more than a piece of clothing. It embodies the spirit of early twentieth-century American Western style—a time when garments were built for a life of hard travel, hunting, and adventure.
Just as important is the personal connection. Brian describes Hemingway’s obvious affection for this vest made recreating it feel less like manufacturing a garment and more like paying tribute to a piece of his legacy. As he continues writing my book, Hemingway Style, there seemed to be no better way to understand the foundations of his enduring aesthetic, Brian says, than by recreating the very garments that defined his wardrobe. By the late 1950s, Hemingway’s original had taken on the deep patina that only decades of wear can produce and had been thoughtfully modified with ammunition loops, transforming it from stylish frontier attire into a well-used hunting companion. Pauline also had a matching one.
The vest seems to have stuck with Hemingway through most of his life, as it appears in photos from his trips to the L-T Ranch in Wyoming from 1931-1936, through the end of his life. At least the late 1950’s or possibly 1960. Needless to say, the vest must have meant something to him, as it stuck with him for at least 20 years. I’ve also found some pictures of what I think is the Ralph Lauren vest inspired by Hemingway’s. It’s not exact, but it’s really similar, but Brian’s version is exact.
I love all of the photos he curated on style from this period, and I’ll add one of my own curated photos of Gerry Spence, famous trial lawyer from Wyoming, with his version of a similar vest, which is also of great style:
