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.

Bohemian Hand Crafted Wool Felt Gaucho Hat - Biltmore Hats
Bohemian Hand Crafted Wool Felt Gaucho Hat - Biltmore Hats
$ 119.00

Bohemian Hand Crafted Wool Felt Gaucho Hat - Biltmore Hats

Stunning distressed wool felt gaucho style hat. Telescope crown with flat top and straight sidewalls. 4" wide stiff flat brim. Grosgrain ribbon ban...

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$ 119.00
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
Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats
$ 42.00

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

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

Wide brim gaucho style flat crown sun hat. Flat brim, 4" wide. Wide ribbon band with side bow. UPF 50+ sun protection. Inner drawstring to adjust s...

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$ 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

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

Brooklyn Hats - Pattaya Braided Raffia Gaucho 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
Raffia Braid Boater - SetarTrading Hats
Raffia Braid Boater - SetarTrading Hats
$ 28.00

Raffia Braid Boater Hat with Black Ribbon Band - Boardwalk Style

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
Small Brim Bolero Style Wool Felt Hat by JSA for Women - SetarTrading Hats
Small Brim Bolero Style Wool Felt Hat by JSA for Women - SetarTrading Hats
$ 37.00

Small Brim Bolero Style Wool Felt Hat by JSA for Women

Adorable little bolero hat with small, 2" wide flat brim. Wool felt bow and tie band. Flat, square crown. Satin inner band with elastic tie. One si...

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$ 37.00