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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.


  • $ 38.00
    Scala Hats

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

    2 colors available

    Woven raffia gambler style golf hat. Turtle tape band with loop. Flat crown. 3" wide curled brim. Wide moisture wicking elasticized SCALA sweatband...

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    $ 38.00
  • $ 132.00
    Scala Hats

    Orleans Handwoven Panama Gambler Hat - Scala Classico Mens Hats

    1 color available

    Handwoven Ecuadorian gambler style Panama hat. Shaped and detailed in the USA. Curled edge brim, 3" wide. Crown 4". 12-Ligne grosgrain;band with si...

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    $ 132.00
  • $ 39.00
    Tula Hats

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

    1 color available

    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
  • $ 20.00
    Milani Hats

    Twisted Toyo Gambler Hat with Black Band - Milani Hats

    1 color available

    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 fiber hat with lattice vented crown chin strap tula hats
    from $ 37.00
    Tula Hats

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

    1 color available

    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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    from $ 37.00
  • Save 36%
    Original Price $ 30.00
    Current Price $ 19.20
    Stacy Adams Hats

    Shiny Polybraid Porkpie Hat - Stacy Adams

    1 color available

    Soft polybraid flat crown porkpie style hat. Shapeable brim, 2.25" wide. Grosgrain band with faux leather overlay. Loop with Stacy Adams pin. Faux ...

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    Original Price $ 30.00
    Current Price $ 19.20
    Save 36%
  • Save 39%
    Original Price $ 25.00
    Current Price $ 15.20
    Stacy Adams Hats

    Shiny Polybraid Porkpie Fedora - Stacy Adams

    2 colors available

    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%
  • Save 41%
    Original Price $ 19.00
    Current Price $ 11.25
    Milani Hats

    Bangkok Toyo Gambler Hat - Milani Hats

    1 color available

    Two tone woven bangkok toyo gambler style hat for men. Brim is curled up, 3" wide. Sunken crown with slighty tapered sidewall. Decorative vented de...

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    Original Price $ 19.00
    Current Price $ 11.25
    Save 41%
  • Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats - SetarTrading Hats
    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats - SetarTrading Hats
    $ 82.00
    Biltmore Hats

    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats

    1 color available

    Genuine hand woven toyo gaucho style hat. Square crown with flat top and straight sidewalls. 4" wide flat brim. Grosgrain ribbon band with leather ...

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    $ 82.00
  • $ 77.00
    Biltmore Hats

    Trendsetter Shantung Porkpie - Biltmore Hats

    1 color available

    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
  • $ 10.00
    JRPalacios

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

    1 color available

    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
  • $ 28.00
    Scala Hats

    Polybraid Gambler Hat with Embroidered Band - Scala Hats

    1 color available

    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 - SetarTrading Hats
    $ 64.25
    Scala Hats

    Braided Laichow Boater with Red and Navy Band - Scala Hats

    1 color available

    Stiff braided laichow boater style hat. Square, flat crown. Straight 2" wide brim. Red and navy striped grosgrain ribbon band and bow. Cotton inner...

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    $ 64.25
  • $ 37.00
    Jeanne Simmons

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

    1 color available

    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
  • $ 48.00
    Scala Hats

    Pro Golf Woven Palm Gambler - Scala Hats for Men

    1 color available

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

    Tommy Bahama Palm Gambler Hat with 3-Pleat Cotton Band

    2 colors available

    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
  • Brooklyn Hats - Ida Wool Felt Telescope - SetarTrading Hats
    Brooklyn Hats - Ida Wool Felt Telescope - SetarTrading Hats
    Save 57%
    Original Price $ 55.00
    Current Price $ 23.55
    Brooklyn Hat

    Brooklyn Hats - Ida Wool Felt Telescope

    1 color available

    A beautifully made hat by Brooklyn Hat Company. Gently curled up grosgrain ribbon bound, 2" brim. Grosgrain ribbon band with side bow and water tow...

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    Original Price $ 55.00
    Current Price $ 23.55
    Save 57%
  • Sea Grass Gambler Hat - SetarTrading Hats
    Sea Grass Gambler Hat - SetarTrading Hats
    $ 25.00
    Milani Hats

    Sea Grass Gambler Hat - Milani Hats

    1 color available

    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 - SetarTrading Hats
    Raffia Gambler with Bound Brim - SetarTrading Hats
    $ 27.00
    Great hats by Karen Keith

    Raffia Gambler with Bound Brim

    1 color available

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

    $ 27.00
  • $ 29.00
    Great hats by Karen Keith

    Raffia Gambler with Braided Jute Band by Kenny Keith

    1 color available

    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 - SetarTrading Hats
    $ 25.00
    Great hats by Karen Keith

    White Toyo Gambler Golf Hat by Kenny Keith

    1 color available

    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
  • Summer Gambler Hat - SetarTrading Hats
    Summer Gambler Hat - SetarTrading Hats
    $ 20.00
    Jeanne Simmons

    Summer Gambler Hat

    2 colors available

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

    $ 20.00