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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.

  • Two Tone Wide Brim Gambler Hat with Shells Accent - Sun 'N' Sand, Gambler Hat - SetarTrading Hats
    Sun N Sand Hats

    Two Tone Wide Brim Gambler Hat with Shells Accent - Sun 'N' Sand

    $ 33.75

    Milan woven two tone gambler style women's hat. Sunken flat crown top with straight sidewalls. Wide curled up edge brim, 4". Twisted raffia and she...

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    $ 33.75
  • Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand, Gambler Hat - SetarTrading Hats
    Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand, Gambler Hat - SetarTrading Hats
    Sun N Sand Hats

    Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand

    $ 33.25

    Women's gambler hat with contrast color inline band. Sunken crown top with straight sidewalls. Curled up 3.5" wide brim. Braided leatherette tie an...

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    $ 33.25
  • Straw Gaucho Hat with Rope Tie - Jeanne Simmons Hats, Bolero Hat - SetarTrading Hats
    Straw Gaucho Hat with Rope Tie - Jeanne Simmons Hats, Bolero Hat - SetarTrading Hats
    Sun N Sand Hats

    Straw Gaucho Hat with Rope Tie - Jeanne Simmons Hats

    $ 31.00

    Stylish gaucho hat with sunken crown top. Flat brim with slight front to back curve, 4" wide. Straight brim side walls. Crown is 3.5" deep. Multi s...

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    $ 31.00
  • Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

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

    $ 39.00

    Woven raffia gambler hat. Slightly tapered crown, telescope crown top. Pineapple and palm tree tape band with loop detail. Palm tree pin. Curled ed...

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    $ 39.00
  • Flat Crown Wide Brim Sun Protection Hat - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    Flat Crown Wide Brim Sun Protection Hat - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    Sun N Sand Hats

    Flat Crown Wide Brim Sun Protection Hat - Sun 'N' Sand Hat

    $ 35.00

    Gaucho style flat crown UV blocking sun hat. Wide brim with curled up edge, 4.5" wide. Wide black ribbon band with straw trim. UPF 50+ sun protecti...

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    $ 35.00
  • Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    Sold out
    Sun N Sand Hats

    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat

    $ 33.00

    Gaucho style flat crown sun protective summer hat. Turned up brim, 4" wide. 4-Pleat chiffon band with loop in back. UPF 50+ sun protection hat. Pac...

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    $ 33.00
  • Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat, Bolero Hat - SetarTrading Hats
    Sun N Sand Hats

    Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat

    $ 33.00

    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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    $ 33.00
  • Wool Felt Boater Hat with Tassel Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Wool Felt Boater Hat with Tassel Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Scala Hats

    Wool Felt Boater Hat with Tassel Band - Scala Hats

    $ 59.75

    Soft wool felt flat top bolero style hat. Flat underwelt brim, 3" wide. Faux suede band with metal loop and tassel detail. Scala pin. Satin inner b...

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    $ 59.75
  • Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats, Gambler Hat - SetarTrading Hats
    Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats, Gambler Hat - SetarTrading Hats
    Sun N Sand Hats

    Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats

    $ 38.00

    Elegant gambler style summer hat for women. Braided organic raffia hat. Wide chiffon scarf tied into long bow knot. Palm tree pin detail. Turned up...

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    $ 38.00
  • 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

    $ 43.00

    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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    $ 43.00
  • 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
    Scala Hats

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

    $ 39.00

    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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    $ 39.00
  • Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats, Gambler Hat - SetarTrading Hats
    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats, Gambler Hat - SetarTrading Hats
    Tula Hats

    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats

    $ 45.00

    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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    $ 45.00
  • 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
    Boardwalk Style Hats

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

    $ 24.00

    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
    Caribbean Joe

    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

    $ 38.00

    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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    $ 38.00
  • Twisted Toyo Gambler Hat with Black Band - Milani Hats, Gambler Hat - SetarTrading Hats
    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
  • 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
    Adora Hats

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

    $ 46.00

    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
    Tula Hats

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

    $ 45.00

    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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    $ 45.00
  • Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Save 39%
    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
    Save 39%
  • Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats, Bolero Hat - SetarTrading Hats
    Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats, Bolero Hat - SetarTrading Hats
    Sun N Sand Hats

    Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats

    $ 31.00

    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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    $ 31.00
  • 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
    Sun N Sand Hats

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

    $ 29.00

    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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    $ 29.00
  • Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats, Gambler Hat - SetarTrading Hats
    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
  • 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
    Texas Gold Hats

    Western Gambler Hat with Gold Band - Texas Gold Hats

    $ 15.00

    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
  • 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
  • Raffia Braid Boater with Stitched Brim, Bolero Hat - SetarTrading Hats
    KW Fashion

    Raffia Braid Boater with Stitched Brim

    $ 33.00

    Flat square crown. Wide grosgrain ribbon band. Decorative stitching. 2.5" wide floppy brim. Drawstring inside crown. One size, fits up to 58.5 cm (...

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    $ 33.00
  • Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats, Bolero Hat - SetarTrading Hats
    Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats, Bolero Hat - SetarTrading Hats
    KW Fashion

    Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats

    $ 32.00

    Flat slighlty tapered crown. Thin black band with decorative beige stitching. Bow tie between two metal studs. Frayed 2" wide flat brim. Drawstring...

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    $ 32.00
  • Two Tone Raffia Bolero by Sun Styles, Bolero Hat - SetarTrading Hats
    Two Tone Raffia Bolero by Sun Styles, Bolero Hat - SetarTrading Hats
    Sun Styles

    Two Tone Raffia Bolero by Sun Styles

    $ 34.00

    Braided raffia bolero style sun hat for women. Black square crown. Natural raffia brim with frayed edge, 4" wide. Ribbon inner band with drawstring...

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    $ 34.00
  • Organic Raffia Gambler for Women - Scala Hats, Gambler Hat - SetarTrading Hats
    Organic Raffia Gambler for Women - Scala Hats, Gambler Hat - SetarTrading Hats
    Scala Hats

    Organic Raffia Gambler for Women - Scala Hats

    $ 51.00

    Organic woven raffia gambler style hat. Beautiful metallic scarf  tied into large bow knot. Turned up, 3" wide brim. Sunken crown top. Elastic Cool...

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    $ 51.00
  • Pro Golf Woven Palm Gambler - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Pro Golf Woven Palm Gambler - Scala Hats for Men

    $ 59.99

    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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    $ 59.99
  • Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat, Bolero Hat - SetarTrading Hats
    Save 18%
    Brooklyn Hat

    Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat

    Original Price $ 40.00
    Current Price $ 32.98

    Urban essentials. Braided raffia gaucho style summer hat. Colorful floral band with fuzzy pom poms. Slightly curved (front to back) brim, 4.75" wid...

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    Original Price $ 40.00
    Current Price $ 32.98
    Save 18%
  • 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 Braid Boater Hat with Black Ribbon Band - Boardwalk Style, Bolero Hat - SetarTrading Hats
    Raffia Braid Boater Hat with Black Ribbon Band - Boardwalk Style, Bolero Hat - SetarTrading Hats
    Boardwalk Style Hats

    Raffia Braid Boater Hat with Black Ribbon Band - Boardwalk Style

    $ 28.00

    An absolute favorite timeless classic hat style. Small, flat brim, 2" wide.  Shallow, short crown with flat top and straight sides. Black grosgrain...

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    $ 28.00
  • 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