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.

Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™
Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™
$ 27.00

Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

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
Twisted Toyo Gambler Hat with Black Band - Milani Hats
$ 20.00

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
Joliet Burnt Palm Leaf Asymmetrical Brim Sun Hat - Tula Hats
Joliet Burnt Palm Leaf Asymmetrical Brim Sun Hat - Tula Hats
$ 48.00

Joliet Burnt Palm Leaf Asymmetrical Brim Sun Hat - 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
gambler burnt palm fiber hat with lattice vented crown chin strap tula hats
$ 36.00

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

1 review

Gambler style sun protection hat with lattice vented crown. Flat crown wall and telescope crown top. Provides excellent sun protection, UPF 50+. Fl...

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$ 36.00
Organic Crochet Raffia Gambler - Sun 'n' Sand
Organic Crochet Raffia Gambler - Sun 'n' Sand
$ 47.00

Organic Crochet Raffia Gambler - Sun 'n' Sand

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

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

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
Trendsetter Shantung Porkpie - Biltmore Hats
Trendsetter Shantung Porkpie - Biltmore Hats
$ 77.00

Trendsetter Shantung Porkpie - Biltmore Hats

Genuine hand woven shantung porkpie style hat. Openweave midcrown 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
Woven Palm Gambler Hat with Studded Band - P.L. Gallera
$ 10.00

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
Polybraid Gambler Hat with Embroidered Band - Scala Hats
$ 28.00

Polybraid Gambler Hat with Embroidered Band - Scala Hats

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 - SetarTrading Hats
$ 50.00

Braided Laichow Boater with Red and Navy Band - Scala Hats

Stiff braided laichow boater style hat. Square, flat crown. Straight 2" wide brim. Red and navy striped grosgrain ribbon band and bow. Cotton inner...

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$ 50.00
Vintage Inspired Straw Boater Hat
Vintage Inspired Straw Boater Hat
$ 24.00

Vintage Inspired Straw Boater Hat

Beautiful lace embellished straw hat for women.  

$ 24.00
Raffia Braid Boater with Stitched Brim
$ 33.00

Raffia Braid Boater with Stitched Brim

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
Raffia Braid Boater with Embroidered Tie
$ 32.00

Raffia Braid Boater with Embroidered Tie

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
Two Tone Raffia Bolero by Sun Styles
$ 34.00

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
Straw Sun Bolero Hat by San Diego Hat Company
Straw Sun Bolero Hat by San Diego Hat Company
$ 43.00

Straw Sun Bolero Hat by 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
Organic Raffia Gambler for Women - Scala Hats
Organic Raffia Gambler for Women - Scala Hats
$ 36.00

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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$ 36.00
Pro Golf Vented Crown Gambler - Scala Hats for Men
$ 48.00

Pro Golf Vented Crown Gambler - Scala Hats for Men

Natural straw color gambler style hat. Three pleat linen band with golf ornament. Turned up, 3" wide brim. Vented sides, sunken crown top. Elastic ...

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$ 48.00
Pro Golf Woven Palm Gambler - Scala Hats for Men
$ 48.00

Pro Golf Woven Palm Gambler - Scala Hats for Men

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
Tommy Bahama Palm Gambler Hat with 3-Pleat Cotton Band - SetarTrading Hats
Tommy Bahama Palm Gambler Hat with 3-Pleat Cotton Band - SetarTrading Hats
$ 51.00

Tommy Bahama Palm Gambler Hat with 3-Pleat Cotton Band

Men's gambler golf hat. Three-pleat cotton band with Tommy Bahama golf coconut button. Handwoven, fine grade. Brim is  3" wide, with curved up edge...

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$ 51.00