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Gambler, Porkpie, Boater, Bolero, Gaucho Hats

Gambler Hats have a low oval shape crown, straight sidewalls, flat telescopic crown top hat with medium to large curled brim. Lately also referred to as Heisenberg, Walter White Breaking Bad hat. Porkpie Hats are small curled brim hats. Sidewalls taper slightly upward. Originally very shallow, now low to medium crown height with set-in top. Its name is a reference to the actual pork pie dish. Often associated with blues and jazz. 

A boater hat is made of straw and has flat brim, straight sidewalls, shallow crown with flat top, typically, accented with a solid color or striped ribbon. Also referred to as straw boater, skimmer, somer, basher, cady. Classic turn of the 20th Century look. Bolero, Gaucho Hats were originally worn by cowboys in South America. These hats are made of felt with wide flat brim, shallow flat crown with chin cord. Think Zorro, or Spanish dancers.

  • Vintage Couture Ivory Toyo Gaucho Hat - Biltmore Hats, Bolero Hat - SetarTrading Hats
    $ 99.00
    Biltmore Hats

    Vintage Couture Ivory Toyo Gaucho Hat - Biltmore Hats

    True craftsmanship American made toyo straw gaucho hat. Elegant, lightweight hat a new addition to Biltmore's Vintage Couture. Now available for sm...

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    $ 99.00
  • Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats, Gambler Hat - SetarTrading Hats
    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats, Gambler Hat - SetarTrading Hats
    $ 39.00
    Tula Hats

    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats

    Great unisex outback gambler sun protection hat for small head sizes. Flat crown wall and telescope crown top. Provides excellent sun protection, U...

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    $ 39.00
  • Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    $ 38.00
    Scala Hats

    Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men

    Woven raffia gambler hat. Turtle tape band with loop detail. 3" wide  brim with curled edge. Wide moisture wicking elasticized SCALA comfort sweatb...

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    $ 38.00
  • Twisted Toyo Gambler Hat with Black Band - Milani Hats, Gambler Hat - SetarTrading Hats
    $ 20.00
    Milani Hats

    Twisted Toyo Gambler Hat with Black Band - Milani Hats

    Summer gambler style hat for men. Twisted toyo straw strands weaved loosely to create this airy ventilated hat. Underside of brim and top of the cr...

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    $ 20.00
  • Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats, Gambler Hat - SetarTrading Hats
    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats, Gambler Hat - SetarTrading Hats
    $ 39.00
    Tula Hats

    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats

    Outback lattice is a gambler style sun protection hat with vented crown. Flat crown wall and telescope crown top. Provides excellent sun protection...

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    $ 39.00
  • Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Save 39%
    Original Price $ 25.00
    Current Price $ 15.20
    Stacy Adams Hats

    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams

    Soft polybraid pinched crown fedora. Small, shapeable brim, 1.75" wide. Faux leather band with tie print overlay. Loop with Stacy Adams pin. Faux l...

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    Original Price $ 25.00
    Current Price $ 15.20
    Save 39%
  • Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats, Gambler Hat - SetarTrading Hats
    $ 99.00
    Biltmore Hats

    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats

    Beautiful American made toyo bolero hat made by Biltmore Hats. Now available in small head sizes for petite heads. Square crown with flat top and s...

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    $ 99.00
  • Woven Palm Gambler Hat with Studded Band - P.L. Gallera, Gambler Hat - SetarTrading Hats
    Woven Palm Gambler Hat with Studded Band - P.L. Gallera, Gambler Hat - SetarTrading Hats
    $ 10.00
    Texas Gold Hats

    Woven Palm Gambler Hat with Studded Band - P.L. Gallera

    Super lightweight gambler style hat for men. Flat crown top, straight vented sidewall. Slightly curled up bround brim, 3.5". Thin studded band. Lea...

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    $ 10.00
  • Polybraid Gambler Hat with Embroidered Band - Scala Hats, Gambler Hat - SetarTrading Hats
    $ 28.00
    Scala Hats

    Polybraid Gambler Hat with Embroidered Band - Scala Hats

    Polybraid gambler style hat. 3" wide brim with turned up edge. Two tone ribbon band with embroidered center. Cotton inner band inside for comfortab...

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    $ 28.00
  • Braided Laichow Boater with Red and Navy Band - Scala Hats, Gambler Hat - SetarTrading Hats
    Braided Laichow Boater with Red and Navy Band - Scala Hats, Gambler Hat - SetarTrading Hats
    $ 64.25
    Scala Hats

    Braided Laichow Boater with Red and Navy Band - Scala Hats

    Gondola braided laichow boater hat. Classic boater with flat crown top. Straight 2" wide brim. Red and navy striped grosgrain ribbon band and bow. ...

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    $ 64.25
  • Gambler - Wool Felt Porkpie Hat by JSA for Men - Brown, Gambler Hat - SetarTrading Hats
    $ 37.00
    Jeanne Simmons

    Gambler - Wool Felt Porkpie Hat by JSA for Men - Brown

    Traditional flat telescope crown top gambler style hat. Double, turquoise and brown grosgrain ribbon band with side bow. Curled, 1.5" wide brim. Ad...

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    $ 37.00
  • Tommy Bahama Palm Gambler Hat with 3-Pleat Cotton Band, Gambler Hat - SetarTrading Hats
    Tommy Bahama Palm Gambler Hat with 3-Pleat Cotton Band, Gambler Hat - SetarTrading Hats
    $ 51.00
    Tommy Bahama Hats

    Tommy Bahama Palm Gambler Hat with 3-Pleat Cotton Band

    Men's gambler golf hat. Three-pleat cotton band with Tommy Bahama golf coconut button. Handwoven, fine grade. Brim is  3" wide, with curved up edge...

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    $ 51.00
  • Raffia Gambler with Bound Brim, Gambler Hat - SetarTrading Hats
    Raffia Gambler with Bound Brim, Gambler Hat - SetarTrading Hats
    $ 27.00
    Great hats by Karen Keith

    Raffia Gambler with Bound Brim

    Soft toyo braid. Braided leatherette band. 3.5" wide curled brim, ribbon bound. Wide elastic band inside. 100% natural fibers.

    $ 27.00
  • Raffia Gambler with Braided Jute Band by Kenny Keith, Gambler Hat - SetarTrading Hats
    $ 29.00
    Great hats by Karen Keith

    Raffia Gambler with Braided Jute Band by Kenny Keith

    Soft braided raffia gambler style golf hat for men. Jute band with loop. Ribbon bound, 3.5" wide curled brim. Wide elasticized comfort inner band. ...

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    $ 29.00
  • White Toyo Gambler Golf Hat by Kenny Keith, Gambler Hat - SetarTrading Hats
    White Toyo Gambler Golf Hat by Kenny Keith, Gambler Hat - SetarTrading Hats
    $ 25.00
    Great hats by Karen Keith

    White Toyo Gambler Golf Hat by Kenny Keith

    White woven toyo gambler style summer hat for men.  Black band with side bow. Gently up turning brim, 3.5" wide. Soft cotton inner band. 100% toyo ...

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    $ 25.00