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The Sassy OliveThe Sassy Olive
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Collection: Bestsellers

Our most-loved headbands, chosen by thousands of happy customers. Shop the bestselling styles and patterns everyone keeps coming back for — soft, comfy, and handmade in Michigan.

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289 products

  • Barbie& Barbie&
    Barbie's Bandana Paisley Wrap Headband
    Barbie's Bandana Paisley Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Madie& Madie&
    Madie's Mushrooms Wrap Headband
    Madie's Mushrooms Wrap Headband
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    $18.00
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    $18.00
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  • Pencil Bows Stretch Headband - The Sassy Olive Pencil Bows Stretch Headband - The Sassy Olive
    Pencil Bows Stretch Headband
    Pencil Bows Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Medusa Wrap Headband - The Sassy Olive Medusa Wrap Headband - The Sassy Olive
    Medusa Wrap Headband
    Medusa Wrap Headband
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    $18.00
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    $18.00
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  • Classic Leopard Print Wrap Headband - The Sassy Olive Classic Leopard Print Wrap Headband - The Sassy Olive
    Classic Leopard Print Wrap Headband
    Classic Leopard Print Wrap Headband
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    $18.00
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    $18.00
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  • Live, Laugh, Leopard Print Wrap Headband - The Sassy Olive Live, Laugh, Leopard Print Wrap Headband - The Sassy Olive
    Live, Laugh, Leopard Print Wrap Headband
    Live, Laugh, Leopard Print Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Moon Landing Wrap Headband - The Sassy Olive Moon Landing Wrap Headband - The Sassy Olive
    Moon Landing Wrap Headband
    Moon Landing Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Colleen Floral Wrap Headband - The Sassy Olive Colleen Floral Wrap Headband - The Sassy Olive
    Colleen Floral Wrap Headband
    Colleen Floral Wrap Headband
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    $18.00
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    $18.00
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  • Snakeskin Wrap Headband - The Sassy Olive Snakeskin Wrap Headband - The Sassy Olive
    Snakeskin Wrap Headband
    Snakeskin Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Yellow Bell Floral Wrap Headband - The Sassy Olive Yellow Bell Floral Wrap Headband - The Sassy Olive
    Yellow Bell Floral Wrap Headband
    Yellow Bell Floral Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Arizona Blue Floral Wrap Headband - The Sassy Olive Arizona Blue Floral Wrap Headband - The Sassy Olive
    Arizona Blue Floral Wrap Headband
    Arizona Blue Floral Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Sun Bleached Splatter Tie Dye Stretch Headband - The Sassy Olive Sun Bleached Splatter Tie Dye Stretch Headband - The Sassy Olive
    Sun Bleached Splatter Tie Dye Stretch Headband
    Sun Bleached Splatter Tie Dye Stretch Headband
    Regular price
    $15.00
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