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.

Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style
Elegant Straw Boater Hat with 3-Pleat Band - Boardwalk Style
$ 24.00

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

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

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® Hats Wool Felt Wide Brim Gambler Hat with Woven Band

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® Hats Wool Felt Gambler Hat with Antique Studded Band

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
Adora® Hats Wool Felt Bolero Hat with Wide Ribbon Side Bow
$ 46.00

Adora® Hats 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 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
Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats
Save $ 13.85
$ 42.00
$ 28.15

Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats

Classy medium brim stiff bolero / gaucho style women's hat. Square crown with flat top and slightly tapering sidewalls. 3" wide flat brim. White le...

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$ 42.00
$ 28.15
Save $ 13.85
Shiny Polybraid Porkpie Hat - Stacy Adams
Save $ 10.80
$ 30.00
$ 19.20

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
$ 19.20
Save $ 10.80
Shiny Polybraid Porkpie Fedora - Stacy Adams
Shiny Polybraid Porkpie Fedora - Stacy Adams
Save $ 9.80
$ 25.00
$ 15.20

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
$ 15.20
Save $ 9.80
Bangkok Toyo Gambler Hat - Milani Hats
Bangkok Toyo Gambler Hat - Milani Hats
Save $ 7.75
$ 19.00
$ 11.25

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
$ 11.25
Save $ 7.75
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
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
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

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

1 review

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 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