Skip to content

Gambler, Porkpie, Boater, Bolero, Gaucho Hats

Gambler 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 Hats are 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. 

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 Hats were 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.

  • $ 25.00
    San Diego Hat Company

    Petite Boater Hat with Gingham Band - San Diego Hat

    Frayed brim boater hat for small head sizes. Flat brim, 2.5" wide. Flat crown. Blue gingham band. Small size, fits up to 54 cm, kid 8-12 years. 100...

    View full details
    $ 25.00
  • $ 39.00
    Tula Hats

    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats

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

    View full details
    $ 39.00
  • $ 38.00
    Scala Hats

    Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men

    Woven raffia gambler style golf hat. Turtle tape band with loop. Flat crown. 3" wide curled brim. Wide moisture wicking elasticized SCALA sweatband...

    View full details
    $ 38.00
  • $ 24.00
    Tula Hats

    Small Heads Outback Burnt Palm Leaf Sun Hat - Tula Hats

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

    View full details
    $ 24.00
  • $ 24.00
    Boardwalk Style Hats

    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. ...

    View full details
    $ 24.00
  • $ 20.00
    Milani Hats

    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...

    View full details
    $ 20.00
  • ad1020a adora hats wool felt women's gambler with braided soft wool tie black
    $ 45.00
    Adora Hats

    Adora® Wool Hat - 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...

    View full details
    $ 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

    Adora® Wool Hat - 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...

    View full details
    $ 45.00
  • ad1021 adora hats wool felt gambler with woven antique studded faux leather trim
    $ 46.00
    Adora Hats

    Adora® Wool Hat - 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...

    View full details
    $ 46.00
  • ad1017 adora hatsa wool felt gambler bolero hat with grosgrain ribbon bow
    $ 46.00
    Adora Hats

    Adora® Wool Hat - 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....

    View full details
    $ 46.00
  • gambler burnt palm fiber hat with lattice vented crown chin strap tula hats
    from $ 37.00
    Tula Hats

    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats

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

    View full details
    from $ 37.00
  • Save 33%
    Original Price $ 42.00
    Current Price $ 28.15
    Brooklyn Hat

    Black Wool Felt Gaucho Hat - Seville by Brooklyn Hats

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

    View full details
    Original Price $ 42.00
    Current Price $ 28.15
    Save 33%
  • Save 39%
    Original Price $ 25.00
    Current Price $ 15.20
    Stacy Adams Hats

    Shiny Polybraid Porkpie Fedora Hat - 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...

    View full details
    Original Price $ 25.00
    Current Price $ 15.20
    Save 39%
  • Chitre Flat Crown Summer Gaucho Hat - Sun 'n' Sand - SetarTrading Hats
    from $ 22.00
    Sun'N'Sand Hats

    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...

    View full details
    from $ 22.00
  • $ 10.00
    Texas Gold Hats

    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...

    View full details
    $ 10.00
  • $ 15.00
    Texas Gold Hats

    Western Gambler Hat with Gold Band - Texas Gold Hats

    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...

    View full details
    $ 15.00
  • $ 28.00
    Scala Hats

    Polybraid Gambler Hat with Embroidered Band - Scala Hats

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

    View full details
    $ 28.00
  • Braided Laichow Boater with Red and Navy Band - Scala - SetarTrading Hats
    $ 64.25
    Scala Hats

    Braided Laichow Boater with Red and Navy Band - Scala Hats

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

    View full details
    $ 64.25