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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.

  • Wool Felt Flat Top Boater Hat - Biltmore Made in USA, Gambler Hat - SetarTrading Hats
    Biltmore Hats

    Wool Felt Flat Top Boater Hat - Biltmore Made in USA

    $ 125.00

    Stunning soft wool felt flat top vintage couture hat. Slightly tapered crown sidewalls. Flat brim 2.75" wide. Grosgrain ribbon band with knot and f...

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    $ 125.00
  • Vintage Couture Ivory Toyo Gaucho Hat - Biltmore Hats, Bolero Hat - SetarTrading Hats
    Biltmore Hats

    Vintage Couture Ivory Toyo Gaucho Hat - Biltmore Hats

    $ 99.00

    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
    Tula Hats

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

    $ 39.00

    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
  • Outback Burnt Palm Leaf Sun Hat, 2XL - Tula Hats, Gambler Hat - SetarTrading Hats
    Outback Burnt Palm Leaf Sun Hat, 2XL - Tula Hats, Gambler Hat - SetarTrading Hats
    Tula Hats

    Outback Burnt Palm Leaf Sun Hat, 2XL - Tula Hats

    $ 39.00

    Great unisex outback gambler sun protection hat. Flat crown wall and telescope crown top. Provides excellent sun protection, UPF 50+. Flat brim wit...

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    $ 39.00
  • Twisted Toyo Gambler Hat with Black Band - Milani Hats, Gambler Hat - SetarTrading Hats
    Milani Hats

    Twisted Toyo Gambler Hat with Black Band - Milani Hats

    $ 20.00

    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
  • Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Sale
    Stacy Adams Hats

    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams

    Original Price $ 25.00
    Current Price $ 15.20

    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
    Sale
  • Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Biltmore Hats

    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats

    $ 99.00

    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
  • Trendsetter Shantung Porkpie - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Trendsetter Shantung Porkpie - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Biltmore Hats

    Trendsetter Shantung Porkpie - Biltmore Hats

    $ 77.00

    Genuine handmade shantung porkpie style hat. Open weave mid-crown design. Soft, pliable, featherweight hat. 2 3/4" brim. Grosgrain ribbon band with...

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    $ 77.00
  • 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
    Texas Gold Hats

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

    $ 10.00

    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
    Scala Hats

    Polybraid Gambler Hat with Embroidered Band - Scala Hats

    $ 28.00

    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
    Scala Hats

    Braided Laichow Boater with Red and Navy Band - Scala Hats

    $ 64.25

    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
    Jeanne Simmons

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

    $ 37.00

    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
  • Pro Golf Woven Palm Gambler - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Pro Golf Woven Palm Gambler - Scala Hats for Men

    $ 48.00

    Natural straw color gambler style hat. Leather band with golf ornament. Turned up, 3" wide brim. Sunken crown top. Elastic CoolMax® comfort inner b...

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    $ 48.00
  • Sea Grass Gambler Hat - Milani Hats, Gambler Hat - SetarTrading Hats
    Sea Grass Gambler Hat - Milani Hats, Gambler Hat - SetarTrading Hats
    Milani Hats

    Sea Grass Gambler Hat - Milani Hats

    $ 25.00

    Thick sea grass strands weaved loosely. Airy, cool. Underside of brim and top of the crown is lined for good sun protection. Brim 3" wide. Black ba...

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    $ 25.00
  • Raffia Gambler with Bound Brim, Gambler Hat - SetarTrading Hats
    Raffia Gambler with Bound Brim, Gambler Hat - SetarTrading Hats
    Great hats by Karen Keith

    Raffia Gambler with Bound Brim

    $ 27.00

    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
    Great hats by Karen Keith

    Raffia Gambler with Braided Jute Band by Kenny Keith

    $ 29.00

    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
    Great hats by Karen Keith

    White Toyo Gambler Golf Hat by Kenny Keith

    $ 25.00

    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
  • Organic Raffia Gambler with Palm Tree Pin - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Organic Raffia Gambler with Palm Tree Pin - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Organic Raffia Gambler with Palm Tree Pin - Scala Hats for Men

    $ 30.00

    Organic woven raffia gambler hat. Jute band with palm tree pin and leather loops. 3" wide curled brim. 100% natural raffia.

    $ 30.00
  • Summer Gambler Hat, Gambler Hat - SetarTrading Hats
    Summer Gambler Hat, Gambler Hat - SetarTrading Hats
    Jeanne Simmons

    Summer Gambler Hat

    $ 20.00

    2" wide brim. Wide black band. Large only (58cm). 100% paper straw.

    $ 20.00

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