Ernest Hemingway was a man of many hats. His was a movable feast of ways to cover the head. With summer approaching, we may find ourselves sailing or fishing or powerboating. The sun getting in our eyes, we could do worse than to don the sort of cap Hemingway used to fight glare when he was on the water.

But first, a few thoughts on Hemingway and hats. His wardrobe of headgear was not random. He wore hats tied to a time or place. It was a habit born of a humiliation. In the early 1920s, Hemingway had bought a floppy fedora in Freiburg, Germany. He made the mistake of wearing it on a Toronto streetcar. It was greeted with laughter. One of the passengers even challenged him to fight. “There is nothing wrong with the hat. It is a good hat. It shed the rain and keeps the sun out of my eyes. But the first time I wore it in Toronto was the last time.” That was because “there is one thing Toronto demands in clothes,” Hemingway wrote. “That thing is conformation.”

Hemingway’s Freiburg fedora simply did not conform. It was treated as an oddity, and by extension so was he. It was one of the worst things that can happen to a man who fancies himself a he-man: Little girls giggled at the sight of him.

“What do you think he is?” one girl asked the other. They wondered if he might be Harold Lloyd. “This remark was good for laughs halfway down the car,” Hemingway wrote, his cheeks no doubt reddening at the memory. That hat humiliation may explain why Hemingway would later in life wear hats that were suited to the time and place. Consider the conformity with which Hemingway covered his head: He would wear a black beret in Paris. He would wear a beret in Basque Country. On safari, he wore a safari hat. It was khaki, like his bush jacket. The left side was pinned up in the Australian fashion.

As a World War II correspondent from the front (well, from the liberated Ritz Paris bar), he wore a G.I. steel helmet. In 1924, Man Ray photographed Ernest in Paris, where Hemingway wore a buffoonish Pulcinella hat. It didn’t quite cover the bandages wrapped around his head since he banged it on an overhead window casement. The girls on the Toronto streetcar would no doubt have laughed, but it did conform to expectations of a Man Ray portrait.

Older, he wore the sort of flat tweed cap that looks best if one is behind the wheel of a 1959 MGA 1600 roadster. Hemingway didn’t need a roadster to make a tweed cap look good.

One of the most distinctive hats was the cap the old man wore when at sea. It was a sort of baseball cap with a low crown and a long bill. He had more than one of the wonderful curiosities. There was the cap all in khaki cotton. And then there was the same hat, but with a black bill that was dark green on the underside. Both are still made, and made in America, by Quaker Marine Supply. The black-billed version is called the “Oysterman.” Hemingway wore them both the same way, at a jaunty, amused angle.

I just bought an Oysterman of my own. Now all I need to make the coming summer complete is a boat. And short of that, perhaps some frozen daiquiris made the Heming-way, with grapefruit juice, not just lime, and sweetened with maraschino liqueur. Giggle if you like.

Eric Felten is the James Beard Award-winning author of How’s Your Drink?