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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.

  • Crushable Wool Felt Bolero Hat with Suede Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Crushable Wool Felt Bolero Hat with Suede Band - Scala Hats, Bolero Hat - SetarTrading Hats
    Scala Hats

    Crushable Wool Felt Bolero Hat with Suede Band - Scala Hats

    $ 59.75

    Soft, crushable wool felt flat top bolero style hat. Slightly floppy raw edge brim, 3.5" wide. Distressed faux suede band with braided overlay. Fea...

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    $ 59.75
  • Wool Felt Flat Top Boater Hat - Biltmore Made in USA, Gambler Hat - SetarTrading Hats
    Biltmore Hats

    Wool Felt Flat Top Boater Hat - Biltmore Made in USA

    $ 125.00

    Stunning soft wool felt flat top vintage couture hat. Slightly tapered crown sidewalls. Flat brim 2.75" wide. Grosgrain ribbon band with knot and f...

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    $ 125.00
  • 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
  • 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

    $ 39.00

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

    Outback Burnt Palm Leaf Sun Hat, 2XL - Tula Hats

    2 reviews
    $ 39.00

    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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    $ 39.00
  • 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
  • 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 Wide Brim Gambler Hat with Woven Band, Gambler Hat - SetarTrading Hats
    Adora® Wool Hat - Wool Felt Wide Brim Gambler Hat with Woven Band, Gambler Hat - SetarTrading Hats
    Adora Hats

    Adora® Wool Hat - Wool Felt Wide Brim Gambler Hat with Woven Band

    $ 45.00

    Wool felt gambler style hat for women. Flat crown. Woven two tone band. Curved edge wide brim, 3.5" wide. Inner drawstring to adjust fit. Wool hats...

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    $ 45.00
  • 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
  • Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats, Gambler Hat - SetarTrading Hats
    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats, Gambler Hat - SetarTrading Hats
    Brooklyn Hat

    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats

    $ 42.00

    Classy medium brim structured felt bolero, gaucho style women's hat. Square crown with flat top and slightly tapering sidewalls. 3" wide flat brim....

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    $ 42.00
  • Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Sale
    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
    Sale
  • Organic Crochet Raffia Gambler - Sun 'N' Sand Hats, Gambler Hat - SetarTrading Hats
    Organic Crochet Raffia Gambler - Sun 'N' Sand Hats, Gambler Hat - SetarTrading Hats
    Sun N Sand Hats

    Organic Crochet Raffia Gambler - Sun 'N' Sand Hats

    1 review
    $ 61.00

    Organic raffia gambler style summer hat for women. Soft crocheted raffia hat. Chiffon scarf tied into long bow knot. Turned up 3" wide brim. Sunken...

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    $ 61.00
  • 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

    $ 22.00

    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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    $ 22.00
  • 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

    1 review
    $ 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

    1 review
    $ 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
  • Polybraid Gambler Hat with Embroidered Band - Scala Hats, Gambler Hat - SetarTrading Hats
    Scala Hats

    Polybraid Gambler Hat with Embroidered Band - Scala Hats

    $ 28.00

    Polybraid gambler style hat. 3" wide brim with turned up edge. Two tone ribbon band with embroidered center. Cotton inner band inside for comfortab...

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    $ 28.00
  • 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
  • Vintage Inspired Straw Boater Hat, Bolero Hat - SetarTrading Hats
    Vintage Inspired Straw Boater Hat, Bolero Hat - SetarTrading Hats
    818

    Vintage Inspired Straw Boater Hat

    $ 24.00

    Beautiful lace embellished straw hat for women.  

    $ 24.00
  • 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
  • Straw Sun Bolero Hat by San Diego Hat Company, Bolero Hat - SetarTrading Hats
    Straw Sun Bolero Hat by San Diego Hat Company, Bolero Hat - SetarTrading Hats
    San Diego Hat Company

    Straw Sun Bolero Hat by San Diego Hat Company

    $ 43.00

    Woven straw sun hat with black stitching detail. Slightly floppy flat, 5" wide brim. Straight crown wall, with flat sunk-in crown top.  Black jute ...

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    $ 43.00
  • Gambler - Wool Felt Porkpie Hat by JSA for Men - Brown, Gambler Hat - SetarTrading Hats
    Jeanne Simmons

    Gambler - Wool Felt Porkpie Hat by JSA for Men - Brown

    $ 37.00

    Traditional flat telescope crown top gambler style hat. Double, turquoise and brown grosgrain ribbon band with side bow. Curled, 1.5" wide brim. Ad...

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    $ 37.00
  • 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

    $ 36.00

    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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    $ 36.00
  • Pro Golf Woven Palm Gambler - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Pro Golf Woven Palm Gambler - Scala Hats for Men

    $ 48.00

    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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    $ 48.00
  • Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat, Bolero Hat - SetarTrading Hats
    Brooklyn Hat

    Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat

    $ 40.00

    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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    $ 40.00
  • 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 Bound Brim, Gambler Hat - SetarTrading Hats
    Raffia Gambler with Bound Brim, Gambler Hat - SetarTrading Hats
    Great hats by Karen Keith

    Raffia Gambler with Bound Brim

    $ 27.00

    Soft toyo braid. Braided leatherette band. 3.5" wide curled brim, ribbon bound. Wide elastic band inside. 100% natural fibers.

    $ 27.00
  • 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
  • White Toyo Gambler Golf Hat by Kenny Keith, Gambler Hat - SetarTrading Hats
    White Toyo Gambler Golf Hat by Kenny Keith, Gambler Hat - SetarTrading Hats
    Great hats by Karen Keith

    White Toyo Gambler Golf Hat by Kenny Keith

    1 review
    $ 25.00

    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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    $ 25.00
  • Organic Raffia Gambler with Palm Tree Pin - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Organic Raffia Gambler with Palm Tree Pin - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Organic Raffia Gambler with Palm Tree Pin - Scala Hats for Men

    $ 30.00

    Organic woven raffia gambler hat. Jute band with palm tree pin and leather loops. 3" wide curled brim. 100% natural raffia.

    $ 30.00
  • Summer Gambler Hat, Gambler Hat - SetarTrading Hats
    Summer Gambler Hat, Gambler Hat - SetarTrading Hats
    Jeanne Simmons

    Summer Gambler Hat

    $ 20.00

    2" wide brim. Wide black band. Large only (58cm). 100% paper straw.

    $ 20.00
  • Summer Porkpie Hat, Gambler Hat - SetarTrading Hats
    Summer Porkpie Hat, Gambler Hat - SetarTrading Hats
    Jeanne Simmons

    Summer Porkpie Hat

    $ 24.00

    2" wide brim. Round crown with dent. Black and white ribbon band with blue accent. Elastic tie in crown. One size fits most. Cotton, polyester

    $ 24.00
  • Small Brim Bolero Style Wool Felt Hat - JSA for Women, Bolero Hat - SetarTrading Hats
    Small Brim Bolero Style Wool Felt Hat - JSA for Women, Bolero Hat - SetarTrading Hats
    Jeanne Simmons

    Small Brim Bolero Style Wool Felt Hat - JSA for Women

    $ 37.00

    Adorable little bolero hat with small, 2" wide flat brim. Wool felt bow and tie band. Flat, square crown. Inner band with elastic tie to adjust siz...

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    $ 37.00
  • Red Wool Felt Bolero Hat - JSA for Women, Bolero Hat - SetarTrading Hats
    Red Wool Felt Bolero Hat - JSA for Women, Bolero Hat - SetarTrading Hats
    Jeanne Simmons

    Red Wool Felt Bolero Hat - JSA for Women

    $ 42.00

    Classic flat crown top, flat brim bolero style wool felt hat. Red grosgrain ribbon band with loop. Flat brim, 3" wide. Satin sweatband with adjusta...

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    $ 42.00

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