Larry Austin, 64, of Palm Harbor, Florida, won the contest on his 10th try on Saturday night in Key West, Florida'ssouthernmostcity.
But Austin said he hasn't gone fishing, a sport immortalized by Ernest Hemingway, since he found out that "you can't catch flounder."
Wearing olive shorts, a cap and a beige fishing shirt, Austin joked that his own writing does not go beyond forging "signatures on life insurance apps."
The look-alike contest was part of the 27th Hemingway Days festival marking the July 21 birthday of the white-bearded author, born 108 years ago in Illinois.
Hemingway, awarded the Nobel Prize in literature in 1954, lived and worked in Key West during the 1930s.
Contestant Graham "Butch" Goodfellow, 54, of Australia said Hemingway and the Australians had some crucial things in common.
"We love to fight, we love to drink and we're big hunters," he said.
First-time contestant Phil Blumer, of Shalimar, Florida was chosen one of 25 finalists.
"They tell me no one wins unless they've entered at least five years," the veterinarian said.
In another event, Bruce Overby, 47, of Los Altos, California, won the Lorian Hemingway Short Story Competition with "Bookmarks," about a man's slide into alcoholism and redemption
