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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
  • Petite Boater Hat with Gingham Band - San Diego Hat, Bolero Hat - SetarTrading Hats
    Petite Boater Hat with Gingham Band - San Diego Hat, Bolero Hat - SetarTrading Hats
    $ 25.00
    San Diego Hat Company

    Petite Boater Hat with Gingham Band - San Diego Hat

    Frayed brim boater hat for small head sizes. Flat brim, 2.5" wide. Flat crown. Blue gingham band. Small size, fits up to 54 cm, kids 8-12 years. 10...

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    $ 25.00
  • 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
  • Small Heads Outback Burnt Palm Leaf Sun Hat - Tula Hats, Gambler Hat - SetarTrading Hats
    Small Heads Outback Burnt Palm Leaf Sun Hat - Tula Hats, Gambler Hat - SetarTrading Hats
    $ 24.00
    Tula Hats

    Small Heads Outback Burnt Palm Leaf Sun Hat - Tula Hats

    Solid crown gambler style sun protection hat for small head sizes. Flat crown wall and telescope crown top. Provides excellent sun protection, UPF ...

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    $ 24.00
  • 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
    $ 39.00
    Tula Hats

    Outback Burnt Palm Leaf Sun Hat, 2XL - 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
  • Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style, Gambler Hat - SetarTrading Hats
    Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style, Gambler Hat - SetarTrading Hats
    $ 24.00
    Boardwalk Style Hats

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

    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
  • Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™, Gambler Hat - SetarTrading Hats
    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™, Gambler Hat - SetarTrading Hats
    $ 33.00
    Sun N Sand Hats

    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

    Women's gaucho hat with chin cord. Soft woven bangkok toyo hat with sunken crown. Curled up 4" wide brim with Aztec pattern ribbon trim. Leatherett...

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    $ 33.00
  • 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
  • Adora® Wool Hat - Wool Felt Gambler Hat with Braided Soft Wool Tie, Gambler Hat - SetarTrading Hats
    $ 45.00
    Adora Hats

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

    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
  • Adora® Wool Hat - Wool Felt Wide Brim Gambler Hat with Woven Band, Gambler Hat - SetarTrading Hats
    Adora® Wool Hat - Wool Felt Wide Brim Gambler Hat with Woven Band, Gambler Hat - SetarTrading Hats
    $ 45.00
    Adora Hats

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

    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
  • Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow, Bolero Hat - SetarTrading Hats
    Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow, Bolero Hat - SetarTrading Hats
    $ 46.00
    Adora Hats

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

    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 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
  • Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats, Gambler Hat - SetarTrading Hats
    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats, Gambler Hat - SetarTrading Hats
    $ 42.00
    Brooklyn Hat

    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats

    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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    $ 42.00
  • 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%
  • Organic Crochet Raffia Gambler - Sun 'N' Sand Hats, Gambler Hat - SetarTrading Hats
    Organic Crochet Raffia Gambler - Sun 'N' Sand Hats, Gambler Hat - SetarTrading Hats
    $ 61.00
    Sun N Sand Hats

    Organic Crochet Raffia Gambler - Sun 'N' Sand Hats

    Organic raffia gambler style summer hat for women. Soft crocheted raffia hat. Chiffon scarf tied into long bow knot. Turned up 3" wide brim. Sunken...

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    $ 61.00
  • Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    $ 22.00
    Sun N Sand Hats

    Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat

    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, 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
  • Trendsetter Shantung Porkpie - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Trendsetter Shantung Porkpie - Biltmore Hats, Gambler Hat - SetarTrading Hats
    $ 77.00
    Biltmore Hats

    Trendsetter Shantung Porkpie - 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
  • 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
  • Western Gambler Hat with Gold Band - Texas Gold Hats, Gambler Hat - SetarTrading Hats
    Western Gambler Hat with Gold Band - Texas Gold Hats, Gambler Hat - SetarTrading Hats
    $ 15.00
    Texas Gold Hats

    Western Gambler Hat with Gold Band - Texas Gold Hats

    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
  • 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