Bob Dylan, the Mad Hatter

‘Dutch Boy’

1961: The “Dutch boy” cap seen on the cover of his debut album was a fixture of Dylan’s early folkie period.

Panamanian Chic

1968: Dylan sported a straw Panama hat for a Saturday Evening Post photo shoot at his home in Woodstock, N.Y.

Rustic Dandy

1969: An affable Dylan doffed his hat for the cover of his Nashville Skyline album.

Western Sizzler

1973: For his role as the enigmatic Alias in director Sam Peckinpah’s downbeat western film Pat Garrett and Billy the Kid, Dylan wore a different hat in every scene.

Hipster Couture

1975: The flat-brimmed hat Dylan wore on his Rolling Thunder Revue tour — also seen on the cover of his 1976 album Desire — was custom-made by Baron Hats of Los Angeles. You can buy a duplicate from the same hatmaker today, for $1,375.

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Boogie Nights

1976: The ’70s brought out some disco style: Dylan wore this white fedora in the concert film The Last Waltz.

Cool and Cozy

1980: Dylan won a Grammy award for Best Rock Vocal for “Gotta Serve Somebody,” then wore this cozy wool cap at the party afterward.

Straw Sophistication

In the video for the song “Inside Out,” recorded with his short-lived supergroup the Traveling Wilburys, Dylan brought out a jaunty straw boater.

Regal Realness

This regal white western topper is another custom job from Baron Hats of Hollywood.

Quintessential Look

These days, Dylan seems particularly fond of flat-brim, flat-crown western dress hats.

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