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.


  • $ 39.00
    Tula Hats

    Outback Burnt Palm Leaf Sun Hat, 2XL - Tula Hats

    1 color available

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

    View full details
    $ 39.00
  • $ 24.00
    Boardwalk Style Hats

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

    1 color available

    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
  • $ 48.00
    Tula Hats

    Joliet Burnt Palm Leaf Asymmetrical Brim Sun Hat - Tula Hats

    1 color available

    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...

    View full details
    $ 48.00
  • 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

    1 color available

    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

    1 color available

    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

    1 color available

    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

    2 colors available

    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

    1 color available

    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

    1 color available

    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%
  • $ 47.00
    Sun'N'Sand Hats

    Organic Crochet Raffia Gambler - Sun 'n' Sand

    2 colors available

    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...

    View full details
    $ 47.00
  • 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

    3 colors available

    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
  • Cativa Flat Crown Floppy Hat - Sun 'n' Sand - SetarTrading Hats
    Cativa Flat Crown Floppy Hat - Sun 'n' Sand - SetarTrading Hats
    $ 22.00
    Sun'N'Sand Hats

    Cativa Flat Crown Floppy Hat - Sun 'n' Sand

    3 colors available

    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...

    View full details
    $ 22.00
  • Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats - SetarTrading Hats
    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats - SetarTrading Hats
    $ 82.00
    Biltmore Hats

    Bohemian Hand Woven Toyo Gaucho Hat - Biltmore Hats

    1 color available

    Genuine hand woven toyo gaucho style hat. Square crown with flat top and straight sidewalls. 4" wide flat brim. Grosgrain ribbon band with leather ...

    View full details
    $ 82.00
  • $ 77.00
    Biltmore Hats

    Trendsetter Shantung Porkpie - Biltmore Hats

    1 color available

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

    View full details
    $ 77.00
  • $ 15.00
    JRPalacios

    Western Gambler Hat with Gold Band - Texas Gold Hats

    3 colors available

    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
  • $ 33.00
    KW Fashion

    Raffia Braid Boater with Stitched Brim

    1 color available

    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 (...

    View full details
    $ 33.00
  • $ 32.00
    KW Fashion

    Raffia Braid Boater with Embroidered Tie

    2 colors available

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

    View full details
    $ 32.00
  • $ 34.00
    Sun Styles

    Two Tone Raffia Bolero by Sun Styles

    1 color available

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

    View full details
    $ 34.00
  • $ 43.00
    San Diego Hat Company

    Straw Sun Bolero Hat by San Diego Hat Company

    1 color available

    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 ...

    View full details
    $ 43.00
  • $ 36.00
    Scala Hats

    Organic Raffia Gambler for Women - Scala Hats

    4 colors available

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

    View full details
    $ 36.00
  • $ 36.00
    Jeanne Simmons

    Wool Felt Porkpie Fedora Hat by JSA -Black

    1 color available

    Wool felt porkpie fedora with wide ribbon band. 2" wide brim. Oval, telescope crown. Ribbon band with drawstring. One size fits most. 100% wool felt.

    $ 36.00
  • Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat - SetarTrading Hats
    $ 40.00
    Brooklyn Hat

    Brooklyn Hats - Pattaya Braided Raffia Gaucho Hat

    1 color available

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

    View full details
    $ 40.00