Skip to content

Filters

Gambler, Porkpie, Boater, Bolero, Gaucho Hats

  • Stunning Wide Brim Ivory and Black Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats HH3158A Ivory Medium (57 cm)
    $ 43.50
    Sun N Sand Hats

    Stunning Wide Brim Ivory and Black Gaucho Hat - Sun 'N' Sand Hats

    This stylish wide-brimmed hat will become your favorite for both casual and formal summer events.  Two-tone, ivory and black, woven pattern. Ivory ...

    View full details
    $ 43.50
  • 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
  • Orbit Twisted Toyo Flat Top Bolero Hat - Biltmore Hats Bolero Hat Biltmore Hats BSTPBLORBT6508LG Brown Large (59 cm)
    $ 85.00
    Biltmore Hats

    Orbit Twisted Toyo Flat Top Bolero Hat - Biltmore Hats

    Beautiful twisted toyo bolero hat made in the USA. Square crown with flat top and straight sidewalls. Flat brim, 3.25" wide. Grosgrain ribbon band ...

    View full details
    $ 85.00
  • 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
  • Vintage Couture Ivory Toyo Gaucho Hat - Biltmore Hats Bolero Hat Biltmore Hats BS88BLOHE40SM Ivory Small (55 cm)
    $ 99.00
    Biltmore Hats

    Vintage Couture Ivory Toyo Gaucho Hat - Biltmore Hats

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

    View full details
    $ 99.00
  • 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
  • Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow Bolero Hat Adora Hats
    Adora® Wool Hat - Wool Felt Bolero Hat with Wide Ribbon Side Bow Bolero Hat Adora Hats ad1017c Light Grey Medium (57 cm)
    $ 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
  • 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
  • Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats hh2137B nv Navy Medium (57 cm)
    Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats hh2137C mf Moss green Medium (57 cm)
    $ 29.00
    Sun N Sand Hats

    Cativa Flat Crown Floppy Hat - 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
    $ 29.00
  • 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
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.