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Gambler, Porkpie, Boater, Bolero, Gaucho Hats

Gambler Hat

These 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 Hat

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.

Boater Hat

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 Hat Styles

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.

  • $ 132.00

    Orleans Handwoven Panama Gambler Hat - Scala Classico Mens Hats

    Scala Hats

    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

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

    Tula Hats

    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

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

    Boardwalk Style Hats

    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
  • $ 27.00

    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

    Sun'N'Sand Hats

    Women's gaucho and gambler style hats. Soft woven bangkok toyo hat with sunken crown. Curled up 4" wide brim with Aztec pattern ribbon trim. Leathe...

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    $ 27.00
  • $ 20.00

    Twisted Toyo Gambler Hat with Black Band - Milani Hats

    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
  • $ 48.00

    Joliet Burnt Palm Leaf Asymmetrical Brim Sun Hat - Tula Hats

    Tula Hats

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

    Adora Hats

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

    Adora Hats

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

    Adora Hats

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

    Adora Hats

    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

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

    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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    from $ 37.00
  • Save 33%
    translation missing: en.product.item.price.original $ 42.00
    translation missing: en.product.item.price.current $ 28.15

    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats

    Brooklyn Hat

    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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    translation missing: en.product.item.price.original $ 42.00
    translation missing: en.product.item.price.current $ 28.15
    Save 33%
  • Save 36%
    translation missing: en.product.item.price.original $ 30.00
    translation missing: en.product.item.price.current $ 19.20

    Shiny Polybraid Porkpie Hat - Stacy Adams

    Stacy Adams Hats

    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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    translation missing: en.product.item.price.original $ 30.00
    translation missing: en.product.item.price.current $ 19.20
    Save 36%
  • Save 39%
    translation missing: en.product.item.price.original $ 25.00
    translation missing: en.product.item.price.current $ 15.20

    Shiny Polybraid Porkpie Fedora - Stacy Adams

    Stacy Adams Hats

    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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    translation missing: en.product.item.price.original $ 25.00
    translation missing: en.product.item.price.current $ 15.20
    Save 39%
  • Save 41%
    translation missing: en.product.item.price.original $ 19.00
    translation missing: en.product.item.price.current $ 11.25

    Bangkok Toyo Gambler Hat - Milani Hats

    Milani Hats

    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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    translation missing: en.product.item.price.original $ 19.00
    translation missing: en.product.item.price.current $ 11.25
    Save 41%
  • $ 47.00

    Organic Crochet Raffia Gambler - Sun 'n' Sand

    Sun'N'Sand Hats

    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

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

    Sun'N'Sand Hats

    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

    Cativa Flat Crown Floppy Hat - Sun 'n' Sand

    Sun'N'Sand Hats

    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

    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats

    Biltmore Hats

    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

    Trendsetter Shantung Porkpie - Biltmore Hats

    Biltmore Hats

    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

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

    JRPalacios

    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

    Western Gambler Hat with Gold Band - Texas Gold Hats

    JRPalacios

    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

    Polybraid Gambler Hat with Embroidered Band - Scala Hats

    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 - SetarTrading Hats
    $ 50.00

    Braided Laichow Boater with Red and Navy Band - Scala Hats

    Scala Hats

    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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    $ 50.00