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Gambler, Porkpie, Boater, Bolero, Gaucho Hats

Gambler Hat

These 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 Hat

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.

Boater Hat

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 Hat Styles

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.

  • $ 39.00

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

    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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    $ 39.00
  • $ 24.00

    Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style

    Boardwalk Style Hats

    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
  • $ 27.00

    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

    Sun'N'Sand Hats

    Women's gaucho and gambler style hats. Soft woven bangkok toyo hat with sunken crown. Curled up 4" wide brim with Aztec pattern ribbon trim. Leathe...

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    $ 27.00
  • $ 48.00

    Joliet Burnt Palm Leaf Asymmetrical Brim Sun Hat - Tula Hats

    Tula Hats

    Beautiful palm sun hat with extra wide grosgrain ribbon band and large bow placed uniquely on front just off center. Wide brim on front, 4" that na...

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    $ 48.00
  • ad1020a adora hats wool felt women's gambler with braided soft wool tie black
    $ 45.00

    Adora® Wool Hat - Wool Felt Gambler Hat with Braided Soft Wool Tie

    Adora Hats

    Wool felt gambler style hat for women. Sunken telescope crown. Braided multi color soft wool tie. Curved edge wide brim, 3.25" wide. Inner drawstri...

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    $ 45.00
  • ad1016 wool felt gambler with woven band women's hat by adora
    ad1016 wool felt gambler with woven band women's hat by adora
    $ 45.00

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

    Adora Hats

    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
  • ad1021 adora hats wool felt gambler with woven antique studded faux leather trim
    $ 46.00

    Adora® Wool Hat - Wool Felt Gambler Hat with Antique Studded Band

    Adora Hats

    Wool felt gambler style hat for women. Sunken telescope crown. Tribal pattern band with antique studded faux leather band and frayed trim. Slightly...

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    $ 46.00
  • ad1017 adora hatsa wool felt gambler bolero hat with grosgrain ribbon bow
    $ 46.00

    Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow

    Adora Hats

    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 fiber hat with lattice vented crown chin strap tula hats
    from $ 37.00

    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats

    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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    from $ 37.00
  • Save 33%
    translation missing: en.product.item.price.original $ 42.00
    translation missing: en.product.item.price.current $ 28.15

    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats

    Brooklyn Hat

    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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    translation missing: en.product.item.price.original $ 42.00
    translation missing: en.product.item.price.current $ 28.15
    Save 33%
  • $ 47.00

    Organic Crochet Raffia Gambler - Sun 'n' Sand

    Sun'N'Sand Hats

    Organic raffia gambler style summer hat. Chiffon scarf tied into long bow knot. Turned up, 3" wide brim. Sunken crown top. Wide elastic comfort inn...

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    $ 47.00
  • Chitre Flat Crown Summer Gaucho Hat - Sun 'n' Sand - SetarTrading Hats
    from $ 22.00

    Chitre Flat Crown Summer Gaucho Hat - Sun 'n' Sand

    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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    from $ 22.00
  • Cativa Flat Crown Floppy Hat - Sun 'n' Sand - SetarTrading Hats
    Cativa Flat Crown Floppy Hat - Sun 'n' Sand - SetarTrading Hats
    $ 22.00

    Cativa Flat Crown Floppy Hat - Sun 'n' Sand

    Sun'N'Sand Hats

    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 - SetarTrading Hats
    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats - SetarTrading Hats
    $ 82.00

    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats

    Biltmore Hats

    Genuine hand woven toyo gaucho style hat. Square crown with flat top and straight sidewalls. 4" wide flat brim. Grosgrain ribbon band with leather ...

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    $ 82.00
  • $ 77.00

    Trendsetter Shantung Porkpie - Biltmore Hats

    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
  • $ 15.00

    Western Gambler Hat with Gold Band - Texas Gold Hats

    JRPalacios

    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
  • $ 24.00

    Vintage Inspired Straw Boater Hat

    818

    Beautiful lace embellished straw hat for women.  

    $ 24.00
  • $ 33.00

    Raffia Braid Boater with Stitched Brim

    KW Fashion

    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
  • $ 32.00

    Raffia Braid Boater with Embroidered Tie

    KW Fashion

    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
  • $ 34.00

    Two Tone Raffia Bolero by Sun Styles

    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
  • $ 43.00

    Straw Sun Bolero Hat by San Diego Hat Company

    San Diego Hat Company

    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
  • $ 36.00

    Organic Raffia Gambler for Women - Scala Hats

    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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    $ 36.00
  • $ 36.00

    Wool Felt Porkpie Fedora Hat by JSA -Black

    Jeanne Simmons

    Wool felt porkpie fedora with wide ribbon band. 2" wide brim. Oval, telescope crown. Ribbon band with drawstring. One size fits most. 100% wool felt.

    $ 36.00
  • Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat - SetarTrading Hats
    $ 40.00

    Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat

    Brooklyn 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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    $ 40.00