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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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  • Hidden Owl Stretch Headband - The Sassy Olive Hidden Owl Stretch Headband - The Sassy Olive
    Hidden Owl Stretch Headband
    Hidden Owl Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Stevie Floral Wrap Headband - The Sassy Olive Stevie Floral Wrap Headband - The Sassy Olive
    Stevie Floral Wrap Headband
    Stevie Floral Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Lucille Leopard Stretch - The Sassy Olive Lucille Leopard Stretch - The Sassy Olive
    Lucille Leopard Stretch Headband
    Lucille Leopard Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Pot It Like Its Hot Stretch Headband - The Sassy Olive Pot It Like Its Hot Stretch Headband - The Sassy Olive
    Pot It Like Its Hot Stretch Headband
    Pot It Like Its Hot Stretch Headband
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    $15.00
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    $15.00
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  • Happy Pills Stretch Headband - The Sassy Olive Happy Pills Stretch Headband - The Sassy Olive
    Happy Pills Stretch Headband
    Happy Pills Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Butterflies Wrap - The Sassy Olive Butterflies Wrap - The Sassy Olive
    Butterflies Wrap Headband
    Butterflies Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Mushroom Foraging Stretch Headband - The Sassy Olive Mushroom Foraging Stretch Headband - The Sassy Olive
    Mushroom Foraging Stretch Headband
    Mushroom Foraging Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Where& Where&
    Where's My Coffee Stretch Headband
    Where's My Coffee Stretch Headband
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    $15.00
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    $15.00
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  • Ocean Gray Stretch Headband - The Sassy Olive Ocean Gray Stretch Headband - The Sassy Olive
    Ocean Gray Stretch Headband
    Ocean Gray Stretch Headband
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    $15.00
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    $15.00
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  • Tranquil Tie Dye Stretch Headband - The Sassy Olive Tranquil Tie Dye Stretch Headband - The Sassy Olive
    Tranquil Tie Dye Stretch Headband
    Tranquil Tie Dye Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Toasty Stretch Headband - The Sassy Olive Toasty Stretch Headband - The Sassy Olive
    Toasty Stretch Headband
    Toasty Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Funky Fresh Paisley Stretch Headband - The Sassy Olive Funky Fresh Paisley Stretch Headband - The Sassy Olive
    Funky Fresh Paisley Stretch Headband
    Funky Fresh Paisley Stretch Headband
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    $15.00
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