Skip to content

Filters

Gambler, Porkpie, Boater, Bolero, Gaucho Hats

  • Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats Bolero Hat Adora Hats
    Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats Bolero Hat Adora Hats AD1485A Beige Medium (57 cm)
    $ 31.25
    Adora Hats

    Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats

    Unique pattern knit gaucho hat. Double layer flat brim, 3.5" wide. Straight sidewall crown with sunken crown top. Faux suede cord band with tails. ...

    View full details
    $ 31.25
  • Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats Bolero Hat Scala Hats LW774-BLK Black Medium (57 cm)
    Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats Bolero Hat Scala Hats LW774-CAMEL Camel Medium (57 cm)
    $ 39.99
    Scala Hats

    Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats

    Soft, crushable wool blend bolero gaucho hat. Flat brim, 3.25" wide. Waxed cord band with tails. Scala pin. Ribbon inner band with drawstring to ad...

    View full details
    $ 39.99
  • Two Tone Wide Brim Gambler Hat with Shells Accent - Sun 'N' Sand Gambler Hat Sun N Sand Hats HH2935 Natural Medium (57 cm)
    $ 33.75
    Sun N Sand Hats

    Two Tone Wide Brim Gambler Hat with Shells Accent - Sun 'N' Sand

    Milan woven two tone gambler style women's hat. Sunken flat crown top with straight sidewalls. Wide curled up edge brim, 4". Twisted raffia and she...

    View full details
    $ 33.75
  • Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats
    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats HH2703A Tan M/L (58 cm)
    $ 36.00
    Sun N Sand Hats

    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat

    Gaucho style flat crown sun protective summer hat. Turned up brim, 4" wide. 4-Pleat chiffon band with loop in back. UPF 50+ sun protection hat. Pac...

    View full details
    $ 36.00
  • Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats HH2533B Black Medium (57 cm)
    Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats
    $ 33.00
    Sun N Sand Hats

    Flat Crown Gaucho Hat with Chin Strap - Sun 'N' Sand Hat

    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
    $ 33.00
  • Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats Gambler Hat Sun N Sand Hats HH2603B Olive Medium (57 cm)
    Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats Gambler Hat Sun N Sand Hats HH2603A Ivory Medium (57 cm)
    $ 39.50
    Sun N Sand Hats

    Organic Braided Raffia Up Brim Hat with Sash - Sun 'N' Sand Hats

    Elegant gambler style summer hat for women. Braided organic raffia hat. Wide chiffon scarf tied into long bow knot. Palm tree pin detail. Turned up...

    View full details
    $ 39.50
  • Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats
    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats TU-15000S Burnt Palm Small (56-57 cm)
    $ 43.00
    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
    $ 43.00
  • Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats Gambler Hat Tula Hats
    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats Gambler Hat Tula Hats TU1-5200 Burnt Palm Large (58.5cm)
    $ 45.00
    Tula Hats

    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats

    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
    $ 45.00
  • Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242B Tan Medium (57 cm)
    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242S Natural Medium (57 cm)
    $ 38.00
    Caribbean Joe

    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

    Women's gaucho hat with chin cord. Soft woven bangkok toyo hat with sunken crown. Curled up 4" wide brim with Aztec pattern ribbon trim. Leatherett...

    View full details
    $ 38.00
  • Twisted Toyo Gambler Hat with Black Band - Milani Hats Gambler Hat Milani Hats
    Twisted Toyo Gambler Hat with Black Band - Milani Hats Gambler Hat Milani Hats S14BK Natural
    $ 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
  • Shiny Polybraid Porkpie Fedora Hat - Stacy Adams Fedora Hat Stacy Adams Hats sa609gys Grey Small (21 5/8")
    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams Fedora Hat Stacy Adams Hats sa609bgs Beige Small (21 5/8")
    Sale
    $ 25.00
    $ 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
    $ 25.00
    $ 15.20
    Sale
  • Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats
    Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats hh2141A nt Natural Medium (57 cm)
    $ 31.00
    Sun N Sand Hats

    Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats

    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
    $ 31.00
  • Trendsetter Shantung Porkpie - Biltmore Hats Gambler Hat Biltmore Hats
    Trendsetter Shantung Porkpie - Biltmore Hats Gambler Hat Biltmore Hats bs3npgtrenM Ivory Medium ((22-22 3/8")
    $ 77.00
    Biltmore Hats

    Trendsetter Shantung Porkpie - Biltmore Hats

    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
  • Woven Palm Gambler Hat with Studded Band - P.L. Gallera Gambler Hat Texas Gold Hats
    Woven Palm Gambler Hat with Studded Band - P.L. Gallera Gambler Hat Texas Gold Hats jr7039 Natural Medium
    $ 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
  • Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats Bolero Hat KW Fashion lch135bg Natural M/L (58.5 cm)
    Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats Bolero Hat KW Fashion lch135bk Black M/L (58.5 cm)
    $ 32.00
    KW Fashion

    Raffia Braid Boater with Embroidered Tie - Large Size Women's Hats

    Narrow brim flat crown top boater hat made of raffia straw. Thin black band with decorative beige stitching. Two metal studs detail in the back aro...

    View full details
    $ 32.00
  • Two Tone Raffia Bolero by Sun Styles Bolero Hat Sun Styles
    Two Tone Raffia Bolero by Sun Styles Bolero Hat Sun Styles AH391bk Black/Natural
    $ 34.00
    Sun Styles

    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...

    View full details
    $ 34.00
  • Organic Raffia Gambler for Women - Scala Hats Gambler Hat Scala Hats
    Organic Raffia Gambler for Women - Scala Hats Gambler Hat Scala Hats
    $ 54.99
    Scala Hats

    Organic Raffia Gambler for Women - Scala Hats

    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
    $ 54.99
  • Raffia Gambler with Braided Jute Band by Kenny Keith Gambler Hat Great hats by Karen Keith rm20cm Natural M
    $ 29.00
    Great hats by Karen Keith

    Raffia Gambler with Braided Jute Band by Kenny Keith

    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. ...

    View full details
    $ 29.00
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.