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Gaucho & Bolero Hats for Women

  • Women's Lightweight Gambler Hat with Chin Cord - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats HH3581A Coral L (58 cm)
    Women's Lightweight Gambler Hat with Chin Cord - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats
    $ 43.00
    Sun N Sand Hats

    Women's Lightweight Gambler Hat with Chin Cord - Sun 'N' Sand Hats

    Stay protected and stylish with this women's gambler hat from Sun 'N' Sand. Crafted from lightweight poly-braid, it features a classic flat brim de...

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    $ 43.00
  • Straw Boater Hat with Chin Cord - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats HH3266A Beige Medium (57 cm)
    Straw Boater Hat with Chin Cord - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats HH3266B Tan Medium (57 cm)
    $ 37.00
    Sun N Sand Hats

    Straw Boater Hat with Chin Cord - Sun 'N' Sand Hats

    Elevate your summer style with this charming straw boater hat that combines vintage appeal with practical features. The compact 2.5" brim offers su...

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    $ 37.00
  • Stunning Wide Brim Ivory and Black Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats HH3158A Ivory Medium (57 cm)
    Stunning Wide Brim Ivory and Black Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats
    $ 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 ...

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    $ 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+...

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    $ 43.00
  • Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats Bolero Hat Adora Hats AD1485A Beige Medium (57 cm)
    Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats Bolero Hat Adora Hats
    $ 31.25
    Adora Hats

    Fashion Knit Gaucho Hat with Waxed Cord - Adora® Hats

    Elevate your hat collection with this striking knit gaucho design featuring a distinctive pattern that turns heads. The structured double-layer fla...

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    $ 31.25
  • Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats Bolero Hat Scala Hats LW774-CAMEL Camel Medium (57 cm)
    Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats Bolero Hat Scala Hats LW774-NAT Natural Medium (57 cm)
    $ 39.99
    Scala Hats

    Knit Wool Blend Gaucho Hat with Waxed Cord - Scala Hats

    Step into confidence with this beautifully crafted wool blend gaucho hat that adapts to your adventurous spirit. Its soft, crushable construction p...

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    $ 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 ...

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    $ 85.00
  • Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats HH2703C Natural M/L (58 cm)
    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats
    $ 36.00
    Sun N Sand Hats

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

    Take command of your sun protection with this striking gaucho-inspired hat that empowers you to stay safe without sacrificing style. The bold flat ...

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    $ 36.00
  • 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)
    $ 45.00
    Tula Hats

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

    Discover refined sun protection with this distinguished outback gambler hat, expertly crafted for smaller head sizes. Featuring a striking burnt pa...

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    $ 45.00
  • 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

    Engineered for sun-soaked adventures, this unisex outback hat delivers sophisticated style with serious protection. The distinctive flat crown and ...

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    $ 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™

    Elevate your sun style with this charming gaucho hat from Caribbean Joe™. Crafted from soft, breathable bangkok toyo, it features a distinctive sun...

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    $ 38.00
  • Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats HH2141B Toast Medium (57 cm)
    Chitre Flat Crown Summer Gaucho Hat - Sun 'N' Sand Hats Bolero Hat Sun N Sand Hats
    $ 37.00
    Sun N Sand Hats

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

    Own your outdoor adventures with this sophisticated gaucho hat, crafted for women who demand both elegance and protection. The distinctive flat cro...

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    $ 37.00
  • Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats
    Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats hh2137C mf Moss green Medium (57 cm)
    $ 37.00
    Sun N Sand Hats

    Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat

    Embrace effortless summer style with this stunning flat crown gaucho hat, designed for those who refuse to compromise on sun protection or sophisti...

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    $ 37.00
  • 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...

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    $ 77.00
  • 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...

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    $ 32.00
  • 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

    Embrace effortless elegance with this stunning organic raffia gambler hat, designed to elevate your warm-weather wardrobe. The luxurious woven cons...

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    $ 54.99

Bolero hats have Spanish origins, closely tied to traditional Andalusian styles often associated with Córdoba (commonly referenced as the sombrero cordobés / Cordovan hat)—a distinctive look known for its flat crown and broad, flat brim, traditionally made in felt and strongly linked to Spanish traditional dress and performance aesthetics. 

Gaucho hats, by contrast, are associated with the South American gauchos—the horsemen/cowboys of Argentina and Uruguay—and are similarly defined by a flat-topped crown and wide flat brim, often paired with a chin cord (wind tie) for function in open, windy landscapes. 

Today, these styles are beloved for that dramatic, fashion-forward silhouette: a wide flat brim that frames the face and elevates even simple outfits. Think Spanish romance and precision in the Bolero/Cordobés tradition, and rugged equestrian heritage in the Gaucho tradition—two distinct origins, one instantly recognizable statement shape.