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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
  • 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
  • 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
  • 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

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.