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Bob Dylan, the Mad Hatter

See how the folk icon rocked hip lids throughout his career

  • Dutch Boy Cap, Hat, Portrait, Young Bob Dylan, Musician, Fashion, 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.

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  • Panama Hat, Fashion, Portrait, Guitar, Musician, Bob Dylan, Hats, Mad Hatter
    Elliott Landy/Getty Images

    Panamanian Chic

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

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  • Rustic Dandy, Hat, Fashion, Bob Dylan, Musician, Guitar, Portrait, Mad Hatter
    Elliott Landy/Getty Images

    Rustic Dandy

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

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  • Western Hat, Bob Dylan, Fashion, Mad Hatter

    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.

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  • Hipster Couture, Fashion, Bob Dylan, Hats, Portrait, Musician, Mad Hatter
    Ken Regan/Camera 5/Getty Images

    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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  • A young caucasian couple enjoy a dinner outdoors with text that reads keep life fun and your calendar full.

    AARP Offer

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  • Hat, Fashion, On Stage, Concert, Bob Dylan, Musician, Mad Hatter

    Boogie Nights

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

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  • Cozy Hat, Fashion, Bob Dylan, Portrait, Smiling, Musician, Mad Hatter
    Ron Galella/WireImage/Getty Images

    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.

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  • Bob Dylan, Hats, Fashion, In Concert, Performing Singer, Mad Hatter
    Neal Preston/Corbis

    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.

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  • Regal Realness, Cowboy Hat, Fashion, On Stage, Concert, Musician, Bob Dylan, Mad Hatter

    Regal Realness

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

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  • Hat, On Stage, Bob Dylan, Musician, Fashion, Mad Hatter
    Derek Storm/Corbis

    Quintessential Look

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

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