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Gambler, Porkpie, Boater, Bolero, Gaucho Hats

  • Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats Bolero Hat Scala Hats LW774-BLK Black Medium (57 cm)
    Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats Bolero Hat Scala Hats LW774-CAMEL Camel Medium (57 cm)
    $ 39.99
    Scala Hats

    Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats

    Soft, crushable wool blend bolero gaucho hat. Flat brim, 3.25" wide. Waxed cord band with tails. Scala pin. Ribbon inner band with drawstring to ad...

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    $ 39.99
  • Twisted Seagrass Gambler Hat with Animal Print Bow - Scala Hats Gambler Hat Scala Hats
    Twisted Seagrass Gambler Hat with Animal Print Bow - Scala Hats Gambler Hat Scala Hats LS106 Natural Medium (57 cm)
    $ 54.00
    Scala Hats

    Twisted Seagrass Gambler Hat with Animal Print Bow - Scala Hats

    Classic twisted seagrass gambler style hat for women. Animal print sheer scarf with long bow.. Straight sidewalls with sunken crown. Up turned brim...

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    $ 54.00
  • Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand Gambler Hat Sun N Sand Hats
    Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand Gambler Hat Sun N Sand Hats HH2933A Ivory Medium (57 cm)
    $ 33.25
    Sun N Sand Hats

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

    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
  • Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR73 Khaki L (59 cm)
    Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR73 Khaki M (57 cm)
    $ 44.99
    Scala Hats

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

    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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    $ 44.99
  • Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats
    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats HH2703A Tan M/L (58 cm)
    $ 33.00
    Sun N Sand Hats

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

    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
  • Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats Gambler Hat Sun N Sand Hats
    Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats Gambler Hat Sun N Sand Hats HH2603C Black Medium (57 cm)
    $ 38.00
    Sun N Sand Hats

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

    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
  • Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats
    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats TU-15000 Burnt Palm Small (55-56 cm)
    $ 43.00
    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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    $ 43.00
  • Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR96-BLK1 Black S/M (21 1/2"-22 1/8")
    Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR96-NAT1 Khaki S/M (21 1/2"-22 1/8")
    $ 44.99
    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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    $ 44.99
  • Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats Gambler Hat Tula Hats
    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats Gambler Hat Tula Hats TU5900 Burnt Palm XXL (62 cm)
    $ 45.00
    Tula Hats

    Outback Burnt Palm Leaf Sun Hat up to 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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    $ 45.00
  • Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242B Tan Medium (57 cm)
    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242S Natural Medium (57 cm)
    $ 38.00
    Caribbean Joe

    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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    $ 38.00
  • Twisted Toyo Gambler Hat with Black Band - Milani Hats Gambler Hat Milani Hats
    Twisted Toyo Gambler Hat with Black Band - Milani Hats Gambler Hat Milani Hats S14BK Natural
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    $ 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
  • Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats Gambler Hat Tula Hats
    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats Gambler Hat Tula Hats TU1-6000 Burnt Palm Small (55 - 56 cm)
    $ 45.00
    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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    $ 45.00
  • Shiny Polybraid Porkpie Fedora Hat - Stacy Adams Fedora Hat Stacy Adams Hats sa609gys Grey Small (21 5/8")
    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams Fedora Hat Stacy Adams Hats sa609bgs Beige Small (21 5/8")
    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%
  • Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats
    Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats hh2141A nt Natural Medium (57 cm)
    $ 31.00
    Sun N Sand Hats

    Chitre Flat Crown Summer Gaucho Hat - 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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    $ 31.00
  • Trendsetter Shantung Porkpie - Biltmore Hats Gambler Hat Biltmore Hats
    Trendsetter Shantung Porkpie - Biltmore Hats Gambler Hat Biltmore Hats bs3npgtrenM Ivory Medium ((22-22 3/8")
    $ 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 Texas Gold Hats
    Woven Palm Gambler Hat with Studded Band - P.L. Gallera Gambler Hat Texas Gold Hats jr7039 Natural Medium
    $ 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
  • Raffia Braid Boater with Stitched Brim Bolero Hat KW Fashion lch125bg Natural
    $ 33.00
    KW Fashion

    Raffia Braid Boater with Stitched Brim

    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 KW Fashion lch135bg Natural
    Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats Bolero Hat KW Fashion lch135bk Black
    $ 32.00
    KW Fashion

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

    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 Sun Styles
    Two Tone Raffia Bolero by Sun Styles Bolero Hat Sun Styles AH391bk Black/Natural
    $ 34.00
    Sun Styles

    Two Tone Raffia Bolero by Sun Styles

    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 Scala Hats
    Organic Raffia Gambler for Women - Scala Hats Gambler Hat Scala Hats
    $ 54.99
    Scala Hats

    Organic Raffia Gambler for Women - Scala Hats

    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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    $ 54.99
  • Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat Bolero Hat Brooklyn Hat bkn1518NT Natural Medium (57 cm)
    Save 18%
    Original Price $ 40.00
    Current Price $ 32.98
    Brooklyn Hat

    Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat

    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%
  • Raffia Braid Boater Hat with Black Ribbon Band - Boardwalk Style Bolero Hat Boardwalk Style Hats
    Raffia Braid Boater Hat with Black Ribbon Band - Boardwalk Style Bolero Hat Boardwalk Style Hats da652nt Natural Medium (57 cm)
    $ 28.00
    Boardwalk Style Hats

    Raffia Braid Boater Hat with Black Ribbon Band - Boardwalk Style

    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 Great hats by Karen Keith rm20cm Natural M
    $ 29.00
    Great hats by Karen Keith

    Raffia Gambler with Braided Jute Band by Kenny Keith

    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
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.

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