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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
  • 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
  • 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
  • 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) Sold out
    $ 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) Sold out
    $ 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
  • 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
  • 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
  • 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
  • White Toyo Gambler Golf Hat by Kenny Keith Gambler Hat Great hats by Karen Keith    White Toyo Gambler Golf Hat by Kenny Keith Gambler Hat Great hats by Karen Keith TM44m Medium (57 cm) White Sold out
    $ 34.00
    Great hats by Karen Keith

    White Toyo Gambler Golf Hat by Kenny Keith

    White woven toyo gambler style summer hat for men.  Black band with side bow. Gently up turning brim, 3.5" wide. Soft cotton inner band. 100% toyo ...

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    $ 34.00
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.