Men's Headwear

Straw porkpie hat with diamond shape crown top. Narrow shapeable brim, 1.5". Multicolor print and solid midnight blue two pleat band. Guitar pin ac...

Waxed bangora straw wide brim gambler hat by Biltmore Vintage Couture. Vertically woven two tone hat with double diamond shape crown top. Open weav...

Woven raffia gambler hat. Slightly tapered crown, telescope crown top. Pineapple and palm tree tape band with loop detail. Palm tree pin. Curled ed...

Structured, water repellent cotton blend hat. Shapeable, stitched and bound brim, 3" wide. Triple Stetson metal eyelets on both side for airflow. W...

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...

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

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

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...

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

Braided toyo pork pie style hats. Recessed flat crown top.  Multicolor striped band with leatherette loop. Up turned, narrow brim, 1.5" wide. Leath...

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

Organic woven raffia gambler style golf hat. Faux leather band with SCALA pin. 3" wide curled brim. Wide moisture wicking elastic sweatband. 100% n...

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

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

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

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...

Classic gamgler style men's hat.  Matching color grosgrain ribbon band with tie print bow. Curled, 1.5" wide brim. Adjustable drawstring in satin b...

Beautifully woven palm fiber gambler style hat. 3" wide brim with turned up edge. 3-pleat tropical print band. Wide elastic band inside for comfort...

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

Soft toyo braid. Tie print 3-pleated band. 3.5" wide curled brim. 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. ...

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

Natural straw color gambler style hat. Black 3-pleat band with golf ornament. 8/10 mm raffia braid. 3" wide brim. Elastic band inside. 100% raffia.

Traditional flat crown top gambler style hat. Black grosgrain ribbon band with tie print bow. Curled, 1.5" wide brim. Adjustable drawstring in sati...