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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

  • F-Word Stretch Headband - The Sassy Olive F-Word Stretch Headband - The Sassy Olive
    F-Word Stretch Headband
    F-Word Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Ansel Stretch - The Sassy Olive Ansel Stretch - The Sassy Olive
    Ansel Stretch Headband
    Ansel Stretch Headband
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    $15.00
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    $15.00
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  • MonsteraStretch Headband - The Sassy Olive MonsteraStretch Headband - The Sassy Olive
    Monstera Stretch Headband
    Monstera Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Cat Mom Stretch Headband - The Sassy Olive Cat Mom Stretch Headband - The Sassy Olive
    Cat Mom Stretch Headband
    Cat Mom Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Vet Clinic Stretch Headband - The Sassy Olive Vet Clinic Stretch Headband - The Sassy Olive
    Vet Clinic Stretch Headband
    Vet Clinic Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Medici Floral Wrap Headband - The Sassy Olive Medici Floral Wrap Headband - The Sassy Olive
    Medici Floral Wrap Headband
    Medici Floral Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Witchy Night Stretch Headband - The Sassy Olive Witchy Night Stretch Headband - The Sassy Olive
    Witchy Night Stretch Headband
    Witchy Night Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Blue Whimsy Cat Stretch Headband Blue Whimsy Cat Stretch Headband - The Sassy Olive
    Blue Whimsy Cat Stretch Headband
    Blue Whimsy Cat Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Madie Mushroom Stretch - The Sassy Olive Madie Mushroom Stretch - The Sassy Olive
    Madie's Mushroom Stretch Headband
    Madie's Mushroom Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Casting Spells Wrap Headband - The Sassy Olive Casting Spells Wrap Headband - The Sassy Olive
    Casting Spells Wrap Headband
    Casting Spells Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Prunella Floral Stretch Headband - The Sassy Olive Prunella Floral Stretch Headband - The Sassy Olive
    Prunella Floral Stretch Headband
    Prunella Floral Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Fresh Lee Stretch - The Sassy Olive Fresh Lee Stretch - The Sassy Olive
    Fresh Lee Stretch Headband
    Fresh Lee Stretch Headband
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    $15.00
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