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.

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
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

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
Shiny Polybraid Porkpie Hat - Stacy Adams
$ 30.00

Shiny Polybraid Porkpie Hat - Stacy Adams

Soft polybraid flat crown porkpie style hat. Shapeable brim, 2.25" wide. Grosgrain band with faux leather overlay. Loop with Stacy Adams pin. Faux ...

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$ 30.00
Shiny Polybraid Porkpie Fedora - Stacy Adams
Shiny Polybraid Porkpie Fedora - Stacy Adams
$ 25.00

Shiny Polybraid Porkpie Fedora - Stacy Adams

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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$ 25.00
Bangkok Toyo Gambler Hat - Milani Hats
Bangkok Toyo Gambler Hat - Milani Hats
$ 19.00

Bangkok Toyo Gambler Hat - Milani Hats

Two tone woven bangkok toyo gambler style hat for men. Brim is curled up, 3" wide. Sunken crown with slighty tapered sidewall. Decorative vented de...

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$ 19.00
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

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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
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
Scala Polybraid Gambler with Embroidered Band
$ 28.00

Scala Polybraid Gambler with Embroidered Band

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

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
Gambler - Wool Felt Porkpie Hat by JSA for Men - Brown
$ 37.00

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

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
Pro Golf Vented Crown Gambler by Scala for Men
$ 48.00

Pro Golf Vented Crown Gambler by Scala 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 by Scala for Men
$ 48.00

Pro Golf Woven Palm Gambler by Scala 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

Three-pleat cotton band with TB golf coconut button. Handwoven, fine grade. Brim is  3" wide, with curved up edge. Flat, set in crown top. Wide ela...

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$ 51.00
Brooklyn Hats - Ida Wool Felt Telescope - SetarTrading Hats
Brooklyn Hats - Ida Wool Felt Telescope - SetarTrading Hats
$ 55.00

Brooklyn Hats - Ida Wool Felt Telescope

A beautifully made hat is a timeless tribute to the days when you tipped your brim with a smile before walking out the door. Brooklyn Hat Co. This ...

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$ 55.00
Sea Grass Gambler Hat - SetarTrading Hats
Sea Grass Gambler Hat - SetarTrading Hats
$ 25.00

Sea Grass Gambler Hat - Milani Hats

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 Gambler with Bound Brim - SetarTrading Hats
Raffia Gambler with Bound Brim - SetarTrading Hats
$ 27.00

Raffia Gambler with Bound Brim

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
$ 29.00

Raffia Gambler with Braided Jute Band by Kenny Keith

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 - SetarTrading Hats
White Toyo Gambler Golf Hat by Kenny Keith
$ 25.00

White Toyo Gambler Golf Hat by Kenny Keith

1

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
Scala Organic Raffia Gambler with Palm Tree Pin - SetarTrading Hats
Scala Organic Raffia Gambler with Palm Tree Pin - SetarTrading Hats
$ 30.00

Scala Organic Raffia Gambler with Palm Tree Pin

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

$ 30.00