Skip to content

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
  • Wide Brim Gambler Hat with Animal Print Scarf - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats HH2523A Natural Medium (57 cm)
    $ 43.00
    Sun N Sand Hats

    Wide Brim Gambler Hat with Animal Print Scarf - Sun 'N' Sand Hats

    Elegant wide-brim flat crown hat for ladies. Flat brim, 3.5" wide, plus 1" turned-up edge. Animal print chiffon scarf with a long tail bow. UPF 50+...

    View full details
    $ 43.00
  • 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
  • Vegan Leather Flat Brim Boater - Scala Hats Bolero Hat Scala Hats
    Vegan Leather Flat Brim Boater - Scala Hats Bolero Hat Scala Hats LW752-BRN Brown Medium (57 cm)
    $ 39.99
    Scala Hats

    Vegan Leather Flat Brim Boater - Scala Hats

    Vegan leather boater hat. Flat crown top with tapering side walls. Bound flat brim, 3" wide. Braided leatherette band. Inner band with drawstring t...

    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
  • Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand Gambler Hat Sun N Sand Hats
    Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand Gambler Hat Sun N Sand Hats HH2933A Ivory Medium (57 cm)
    $ 33.25
    Sun N Sand Hats

    Maslin Straw Gambler Hat with Braided Chin Cord - Sun 'N' Sand

    Women's gambler hat with contrast color inline band. Sunken crown top with straight sidewalls. Curled up 3.5" wide brim. Braided leatherette tie an...

    View full details
    $ 33.25
  • 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
  • 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
  • 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
  • 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
  • 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
    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
    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
  • 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
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.