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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

  • Brain Daisies Stretch Headband - The Sassy Olive Brain Daisies Stretch Headband - The Sassy Olive
    Brain Daisies Stretch Headband
    Brain Daisies Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Geolinda Stretch - The Sassy Olive Geolinda Stretch - The Sassy Olive
    Geolinda Stretch Headband
    Geolinda Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Geolinda Wrap Headband - The Sassy Olive Geolinda Wrap Headband - The Sassy Olive
    Geolinda Wrap Headband
    Geolinda Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Mermaid Mavens Stretch Headband - The Sassy Olive Mermaid Mavens Stretch Headband - The Sassy Olive
    Mermaid Mavens Stretch Headband
    Mermaid Mavens Stretch Headband
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    $15.00
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    $15.00
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  • Hippie Tree Stretch Headband - The Sassy Olive Hippie Tree Stretch Headband - The Sassy Olive
    Hippie Tree Stretch Headband
    Hippie Tree Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Tube Socks Tie Dye Stretch Headband - The Sassy Olive Tube Socks Tie Dye Stretch Headband - The Sassy Olive
    Tube Socks Tie Dye Stretch Headband
    Tube Socks Tie Dye Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • AYSO Stretch Headband - The Sassy Olive AYSO Stretch Headband - The Sassy Olive
    AYSO Stretch Headband
    AYSO Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • First Base Stretch - The Sassy Olive First Base Stretch - The Sassy Olive
    First Base Stretch Headband
    First Base Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Dusk in Autumn Wrap Headband - The Sassy Olive Dusk in Autumn Wrap Headband - The Sassy Olive
    Dusk in Autumn Wrap Headband
    Dusk in Autumn Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Moroccan Summer Wrap Headband - The Sassy Olive Moroccan Summer Wrap Headband - The Sassy Olive
    Moroccan Summer Wrap Headband
    Moroccan Summer Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Live, Laugh, Leopard Stretch Headband - The Sassy Olive Live, Laugh, Leopard Stretch - The Sassy Olive
    Live, Laugh, Leopard Stretch Headband
    Live, Laugh, Leopard Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • 60& 60&
    60's Picnic Blanket Stretch Headband
    60's Picnic Blanket Stretch Headband
    Regular price
    $15.00
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    $15.00
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