Gambler, Porkpie, Boater, Bolero, Gaucho Hats

Soft, crushable wool felt flat top bolero style hat. Slightly floppy raw edge brim, 3.5" wide. Distressed faux suede band with braided overlay. Fea...

Stunning soft wool felt flat top vintage couture hat. Slightly tapered crown sidewalls. Flat brim 2.75" wide. Grosgrain ribbon band with knot and f...

Soft wool felt flat top bolero style hat. Flat underwelt brim, 3" wide. Faux suede band with metal loop and tassel detail. Scala pin. Satin inner b...

True craftsmanship American made toyo straw gaucho hat. Elegant, lightweight hat a new addition to Biltmore's Vintage Couture. Now available for sm...

Great unisex outback gambler sun protection hat for small head sizes. Flat crown wall and telescope crown top. Provides excellent sun protection, U...

Woven raffia gambler hat. Turtle tape band with loop detail. 3" wide  brim with curled edge. Wide moisture wicking elasticized SCALA comfort sweatb...

Solid crown gambler style sun protection hat for small head sizes. Flat crown wall and telescope crown top. Provides excellent sun protection, UPF ...

Great unisex outback gambler sun protection hat. Flat crown wall and telescope crown top. Provides excellent sun protection, UPF 50+. Flat brim wit...

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. ...

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...

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...

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...

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....

Outback lattice is a gambler style sun protection hat with vented crown. Flat crown wall and telescope crown top. Provides excellent sun protection...

Classy medium brim structured felt bolero, gaucho style women's hat. Square crown with flat top and slightly tapering sidewalls. 3" wide flat brim....

Organic raffia gambler style summer hat for women. Soft crocheted raffia hat. Chiffon scarf tied into long bow knot. Turned up 3" wide brim. Sunken...

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...

Beautiful American made toyo bolero hat made by Biltmore Hats. Now available in small head sizes for petite heads. Square crown with flat top and s...

Genuine handmade shantung porkpie style hat. Open weave mid-crown design. Soft, pliable, featherweight hat. 2 3/4" brim. Grosgrain ribbon band with...

Super lightweight gambler style hat for men. Flat crown top, straight vented sidewall. Slightly curled up bround brim, 3.5". Thin studded band. Lea...

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...

Polybraid gambler style hat. 3" wide brim with turned up edge. Two tone ribbon band with embroidered center. Cotton inner band inside for comfortab...

Gondola braided laichow boater hat. Classic boater with flat crown top. Straight 2" wide brim. Red and navy striped grosgrain ribbon band and bow. ...

Beautiful lace embellished straw hat for women.  

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 (...

Flat slighlty tapered crown. Thin black band with decorative beige stitching. Bow tie between two metal studs. Frayed 2" wide flat brim. Drawstring...

Braided raffia bolero style sun hat for women. Black square crown. Natural raffia brim with frayed edge, 4" wide. Ribbon inner band with drawstring...

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 ...

Traditional flat telescope crown top gambler style hat. Double, turquoise and brown grosgrain ribbon band with side bow. Curled, 1.5" wide brim. Ad...

Organic woven raffia gambler style hat. Beautiful metallic scarf  tied into large bow knot. Turned up, 3" wide brim. Sunken crown top. Elastic Cool...

Natural straw color gambler style hat. Leather band with golf ornament. Turned up, 3" wide brim. Sunken crown top. Elastic CoolMax® comfort inner b...

Urban essentials. Braided raffia gaucho style summer hat. Colorful floral band with fuzzy pom poms. Slightly curved (front to back) brim, 4.75" wid...

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...

An absolute favorite timeless classic hat style. Small, flat brim, 2" wide.  Shallow, short crown with flat top and straight sides. Black grosgrain...

Soft toyo braid. Braided leatherette band. 3.5" wide curled brim, ribbon bound. Wide elastic band inside. 100% natural fibers.

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. ...

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 ...

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

2" wide brim. Wide black band. Large only (58cm). 100% paper straw.

2" wide brim. Round crown with dent. Black and white ribbon band with blue accent. Elastic tie in crown. One size fits most. Cotton, polyester

Adorable little bolero hat with small, 2" wide flat brim. Wool felt bow and tie band. Flat, square crown. Inner band with elastic tie to adjust siz...

Classic flat crown top, flat brim bolero style wool felt hat. Red grosgrain ribbon band with loop. Flat brim, 3" wide. Satin sweatband with adjusta...