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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
  • Vegan Leather Flat Brim Boater - Scala Hats Bolero Hat Scala Hats    Vegan Leather Flat Brim Boater - Scala Hats Bolero Hat Scala Hats LW752-BRN Brown Medium (57 cm)
    $ 39.99
    Scala Hats

    Vegan Leather Flat Brim Boater - Scala Hats

    Vegan leather boater hat. Flat crown top with tapering side walls. Bound flat brim, 3" wide. Braided leatherette band. Inner band with drawstring t...

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    $ 39.99
  • Orbit Twisted Toyo Flat Top Bolero Hat - Biltmore Hats Bolero Hat Biltmore Hats BSTPBLORBT6508LG Brown Large (59 cm)
    $ 85.00
    Biltmore Hats

    Orbit Twisted Toyo Flat Top Bolero Hat - Biltmore Hats

    Beautiful twisted toyo bolero hat made in the USA. Square crown with flat top and straight sidewalls. Flat brim, 3.25" wide. Grosgrain ribbon band ...

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    $ 85.00
  • Two Tone Wide Brim Gambler Hat with Shells Accent - Sun 'N' Sand Gambler Hat Sun N Sand Hats HH2935 Natural Medium (57 cm)
    $ 33.75
    Sun N Sand Hats

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

    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
  • Straw Gaucho Hat with Rope Tie - Jeanne Simmons Hats Bolero Hat Jeanne Simmons JS8082TT Toast Medium (57 cm) Straw Gaucho Hat with Rope Tie - Jeanne Simmons Hats Bolero Hat Jeanne Simmons JS8082BKT Black Tweed Medium (57 cm)
    $ 31.00
    Jeanne Simmons

    Straw Gaucho Hat with Rope Tie - Jeanne Simmons Hats

    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 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 HH2703B Black Tweed 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
  • Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats HH2533B Black Medium (57 cm) Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats
    $ 33.00
    Sun N Sand Hats

    Flat Crown Gaucho Hat with Chin Strap - 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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    $ 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
  • Vintage Couture Ivory Toyo Gaucho Hat - Biltmore Hats Bolero Hat Biltmore Hats BS88BLOHE40SM Ivory Small (55 cm)
    $ 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
  • 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-15000S 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
  • Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style Gambler Hat Boardwalk Style Hats    Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style Gambler Hat Boardwalk Style Hats da1851wh White Medium (57 cm)
    $ 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 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
    $ 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 Bolero Hat with Wide Ribbon Side Bow Bolero Hat Adora Hats    Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow Bolero Hat Adora Hats ad1017c Light Grey Medium (57 cm)
    $ 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 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 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
  • Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats hh2137B nv Navy Medium (57 cm) Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats hh2137C mf Moss green Medium (57 cm)
    $ 29.00
    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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    $ 29.00
  • 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 Embroidered Tie - Large Size Women's Hats Bolero Hat KW Fashion lch135bg Natural M/L (58.5 cm) Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats Bolero Hat KW Fashion lch135bk Black M/L (58.5 cm)
    $ 32.00
    KW Fashion

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

    Narrow brim flat crown top boater hat made of raffia straw. Thin black band with decorative beige stitching. Two metal studs detail in the back aro...

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    $ 32.00
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.