In most places, wearing a thick wool sweater in the dead of summer may raise a few eyebrows. In Key West, it’s all part of the “uniform.”
White beards, broad smiles and a carefully crafted swagger. That’s what rolled into one of Key West’s most legendary bars Thursday night, as the opening round of the 45th Annual Hemingway Look-Alike Contest got underway at Sloppy Joe’s.
Contestants took the stage at the Duval Street saloon, the very place Ernest Hemingway used to hang out during the 1930s while living in Key West.
Some rocked safari attire. Others…his iconic fisherman sweaters. But nearly all brought those signature beards, bravado and the brave face needed to convince a panel of past winners that they were worthy of advancing to the final round.
The “hopefuls” were judged on more than their physical resemblance to Hemingway. They also considered how well they captured the “Papa” persona (as Hemingway was affectionately called), their stage presence and ability to win over the room.
When the night was over, twelve contestants advanced to Saturday night’s final round. A second preliminary round is scheduled for tonight, with the 2026 winner crowned Saturday evening at Sloppy Joe’s.
For many competitors, the annual contest is as much a reunion as it is a competition. It’s an annual pilgrimage to Key West, where they can reconnect with friends who understand the walk, the crowd and the dedication required to dress like Ernest Hemingway in July.
The contest is the highlight of Hemingway Days, an annual Key West celebration of the author’s literary legacy, sporting pursuits and island years. The 2026 festival continues through Sunday with events including the lighthearted “Running” of the Bulls outside Sloppy Joe’s, a dockside fish-off, a street fair and a belated birthday bash marking the 127th anniversary of Hemingway’s July 21 birth.
Beyond the fun, the look-alikes also carry a cause beyond the stage. The Hemingway Look-Alike Society, formed by past winners and contestants, raises money for scholarships for College of the Florida Keys students and has awarded more than $350,000 since its inception.
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