1. Clint Eastwood’s battered straight-brimmed cowboy hat in the 1966 western The Good, the Bad, and the Ugly. It remains the gold standard.
2. Jack Nicholson’s various smooth fedoras in Roman Polanski’s 1974 masterpiece Chinatown.
3. The late artist Dash Snow’s straw boater hat, which he decorated with the pin “nobody for president.”
4. The German artist Joseph Beuys’s trademark fedora.
5. The pink rabbit-eared cap on the young drifter Bunny Boy in Harmony Korine’s 1997 film Gummo.
6. The writer Kurt Vonnegut often wore a comfortable driver’s cap tucked over his forehead like he always had somewhere else to get to.
7. Most men look lazy in baseball caps. Somehow Tom Selleck’s Detroit Tigers’cap in Magnum P.I. seemed stylishly unassuming in an otherwise ostentatious Hawaii.
8. Che Guevara’s star-emblazoned beret—militant and messianic.
9. Musician Tom Waits has made a second career of modeling a trilby perfectly.
10. Perhaps the best men’s hat in the history of painting arrives on the pate of Rembrandt’s “The Polish Rider” with his red fur-lined, black-trimmed hat that matches his pants. He seems ready for anything. BG
Christopher Bollen is not a hat-wearer by nature, and he reluctantly bought his first fedora (as he reports in “The Return of the Hat”). Bollen is a writer and critic who lives in New York. He has written widely on art and culture and worked as an editor at Interview. His first novel, Lightning People, came out in 2011, and he is currently at work on a new novel.
