A Younger Hemingway Emerges at Key West Look-Alike Contest

For the first time in the 45-year history of the Hemingway Look-Alike Contest, the winner does not sport the iconic white beard of the author’s later years. Chris Dutton, a 39-year-old attorney from Tampa, captured the title at Sloppy Joe’s Bar by channeling the dark-haired, mustachioed Hemingway of the 1930s.

Money Talk·July 28, 2026·reads: 751

A Younger Hemingway Emerges at Key West Look-Alike Contest

Dutton secured his win on his seventh attempt, triumphing over 133 other hopefuls during the final round held Saturday, July 25. While the competition traditionally favors the elder "Papa" persona, judges recognized Dutton for capturing the look of the author during his prolific Key West decade, when he penned works like For Whom the Bell Tolls. He credited his success to the support of past winners and a "lucky sweater" gifted to him by David Douglas, president of the Hemingway Look-Alike Society.

The three-day festival, which concluded Sunday, serves as an annual tribute to the writer’s time on the island. Beyond the look-alike competition, the event featured a mock "Running of the Bulls," the Key West Marlin Tournament, and a short story contest judged by Hemingway’s granddaughter, Lorian Hemingway. Pam Morrison of New Zealand took top honors in the writing competition for her story "One Small Bird."

Beyond the festivities, the event maintains a charitable focus. The Hemingway Look-Alike Society used the gathering to award scholarships to students at the College of the Florida Keys, pushing their total contributions past the $350,000 mark. Dutton expressed his intent to leverage his new platform to support the society’s ongoing philanthropic work in both Key West and Cuba.