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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
  • $ 24.00
    Boardwalk Style Hats

    Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style

    1 color available

    Classic flat brim boater style hat. UPF 50+ sun protection hat. 3-Pleat black cotton band. 2.75" wide flat brim. Drawstring inside to reduce size. ...

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    $ 24.00
  • $ 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
  • $ 48.00
    Tula Hats

    Joliet Burnt Palm Leaf Asymmetrical Brim Sun Hat - Tula Hats

    1 color available

    Beautiful palm sun hat with extra wide grosgrain ribbon band and large bow placed uniquely on front just off center. Wide brim on front, 4" that na...

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    $ 48.00
  • ad1020a adora hats wool felt women's gambler with braided soft wool tie black
    $ 45.00
    Adora Hats

    Adora® Wool Hat - Wool Felt Gambler Hat with Braided Soft Wool Tie

    1 color available

    Wool felt gambler style hat for women. Sunken telescope crown. Braided multi color soft wool tie. Curved edge wide brim, 3.25" wide. Inner drawstri...

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    $ 45.00
  • ad1016 wool felt gambler with woven band women's hat by adora
    ad1016 wool felt gambler with woven band women's hat by adora
    $ 45.00
    Adora Hats

    Adora® Wool Hat - Wool Felt Wide Brim Gambler Hat with Woven Band

    1 color available

    Wool felt gambler style hat for women. Flat crown. Woven two tone band. Curved edge wide brim, 3.5" wide. Inner drawstring to adjust fit. Wool hats...

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    $ 45.00
  • ad1021 adora hats wool felt gambler with woven antique studded faux leather trim
    $ 46.00
    Adora Hats

    Adora® Wool Hat - Wool Felt Gambler Hat with Antique Studded Band

    1 color available

    Wool felt gambler style hat for women. Sunken telescope crown. Tribal pattern band with antique studded faux leather band and frayed trim. Slightly...

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    $ 46.00
  • ad1017 adora hatsa wool felt gambler bolero hat with grosgrain ribbon bow
    $ 46.00
    Adora Hats

    Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow

    2 colors available

    Stylish wool felt bolero hat. Telescope crown. Wide grosgrain ribbon band and side bow. Flat, wide brim 3.25" wide. Inner drawstring to adjust fit....

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    $ 46.00
  • 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 33%
    Original Price $ 42.00
    Current Price $ 28.15
    Brooklyn Hat

    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats

    1 color available

    Classy medium brim structured felt bolero, gaucho style women's hat. Square crown with flat top and slightly tapering sidewalls. 3" wide flat brim....

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    Original Price $ 42.00
    Current Price $ 28.15
    Save 33%
  • 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%
  • $ 47.00
    Sun'N'Sand Hats

    Organic Crochet Raffia Gambler - Sun 'n' Sand

    2 colors available

    Organic raffia gambler style summer hat. Chiffon scarf tied into long bow knot. Turned up, 3" wide brim. Sunken crown top. Wide elastic comfort inn...

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    $ 47.00
  • Chitre Flat Crown Summer Gaucho Hat - Sun 'n' Sand - SetarTrading Hats
    from $ 22.00
    Sun'N'Sand Hats

    Chitre Flat Crown Summer Gaucho Hat - Sun 'n' Sand

    3 colors available

    Ladies' gaucho style sun hat. Wide brim gaucho style flat crown sun hat. Flat brim, 4" wide. Wide ribbon band with side bow. UPF 50+ sun protection...

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    from $ 22.00
  • Cativa Flat Crown Floppy Hat - Sun 'n' Sand - SetarTrading Hats
    Cativa Flat Crown Floppy Hat - Sun 'n' Sand - SetarTrading Hats
    $ 22.00
    Sun'N'Sand Hats

    Cativa Flat Crown Floppy Hat - Sun 'n' Sand

    3 colors available

    Wide brim gaucho style flat crown summer hat. Floppy brim, 4" wide. Braided faux suede tie. UPF 50+ sun protection. Packable. Inner drawstring to a...

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    $ 22.00
  • 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
  • $ 15.00
    JRPalacios

    Western Gambler Hat with Gold Band - Texas Gold Hats

    3 colors available

    Stiff gambler style hat for women. Curled brim edge. 3" wide. Narrow decorative gold band. Elastic comfort inner band. Medium, fits up to 58 cm. Im...

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    $ 15.00
  • $ 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