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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.

  • Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats Bolero Hat Adora Hats
    Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats Bolero Hat Adora Hats AD1485A Beige Medium (57 cm)
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    Adora Hats

    Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats

    $ 31.25

    Unique pattern knit gaucho hat. Double layer flat brim, 3.5" wide. Straight sidewall crown with sunken crown top. Faux suede cord band with tails. ...

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    $ 31.25
  • 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)
    Scala Hats

    Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats

    $ 39.99

    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
  • Wool Felt Gaucho Hat with Beads Tassel - Scala Hats Bolero Hat Scala Hats LF259 Black Medium (57 cm)
    Scala Hats

    Wool Felt Gaucho Hat with Beads Tassel - Scala Hats

    $ 62.00

    Telescope crown gaucho hat for women. Under welt brim, 3.75" wide. Braided faux leather band with beads tassel. Scala pin. Satin inner band with dr...

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    $ 62.00
  • 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)
    Scala Hats

    Vegan Leather Flat Brim Boater - Scala Hats

    $ 39.99

    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)
    Biltmore Hats

    Orbit Twisted Toyo Flat Top Bolero Hat - Biltmore Hats

    $ 85.00

    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
  • 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)
    Scala Hats

    Twisted Seagrass Gambler Hat with Animal Print Bow - Scala Hats

    $ 54.00

    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)
    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 Sun N Sand Hats JS8082TT Toast Medium (57 cm)
    Straw Gaucho Hat with Rope Tie - Jeanne Simmons Hats Bolero Hat Sun N Sand Hats JS8082BKT Black Tweed Medium (57 cm)
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    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 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)
    Scala Hats

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

    $ 44.99

    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 Wide Brim Sun Protection Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats HH2644B Tan OS (57 cm)
    Flat Crown Wide Brim Sun Protection Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats HH2644A Ivory OS (57 cm)
    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 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)
    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 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
    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
  • Aphrodite Wool Felt Gaucho Hat with Celestial Charms - Scala Hats Bolero Hat Scala Hats
    Aphrodite Wool Felt Gaucho Hat with Celestial Charms - Scala Hats Bolero Hat Scala Hats LF283-BLK Black Medium (57 cm)
    Scala Hats

    Aphrodite Wool Felt Gaucho Hat with Celestial Charms - Scala Hats

    $ 69.99

    Black wool felt gaucho hat. Slightly floppy raw edge brim, 4" wide. Telescope crown top. Celestial charms over ribbon band. Ribbon inner band with ...

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    $ 69.99
  • Wool Felt Boater Hat with Tassel Band - Scala Hats Bolero Hat Scala Hats LF268 Mink Medium (57 cm)
    Wool Felt Boater Hat with Tassel Band - Scala Hats Bolero Hat Scala Hats LF268 Blush Medium (57 cm)
    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 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)
    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 Biltmore Hats BS88BLOHE40SM Ivory Small (55 cm)
    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 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)
    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 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")
    Scala Hats

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

    $ 44.99

    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
  • Small Heads Outback Burnt Palm Leaf Sun Hat - Tula Hats Gambler Hat Tula Hats
    Small Heads Outback Burnt Palm Leaf Sun Hat - Tula Hats Gambler Hat Tula Hats TU9250 Burnt Palm XXS (50 - 51 cm)
    Tula Hats

    Small Heads Outback Burnt Palm Leaf Sun Hat - Tula Hats

    $ 27.45

    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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    $ 27.45
  • 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)
    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 Boardwalk Style Hats
    Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style Gambler Hat Boardwalk Style Hats da1851wh White Medium (57 cm)
    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 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)
    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 Milani Hats
    Twisted Toyo Gambler Hat with Black Band - Milani Hats Gambler Hat Milani Hats S14BK Natural
    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 Adora Hats
    Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow Bolero Hat Adora Hats ad1017c Light Grey Medium (57 cm)
    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 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)
    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 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%
    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 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)
    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 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)
    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
  • 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")
    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 Texas Gold Hats
    Woven Palm Gambler Hat with Studded Band - P.L. Gallera Gambler Hat Texas Gold Hats jr7039 Natural Medium
    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
  • Raffia Braid Boater with Stitched Brim Bolero Hat KW Fashion lch125bg Natural
    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 KW Fashion lch135bg Natural
    Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats Bolero Hat KW Fashion lch135bk Black
    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 Sun Styles
    Two Tone Raffia Bolero by Sun Styles Bolero Hat Sun Styles AH391bk Black/Natural
    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 Scala Hats
    Organic Raffia Gambler for Women - Scala Hats Gambler Hat Scala Hats
    Scala Hats

    Organic Raffia Gambler for Women - Scala Hats

    $ 54.99

    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
  • Pro Golf Woven Palm Gambler - Scala Hats for Men Gambler Hat Scala Hats 350GOS-NAT2 S/M Natural Palm
    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