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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

  • Goodnight Garden Wrap Headband - The Sassy Olive Goodnight Garden Wrap Headband - The Sassy Olive
    Goodnight Garden Wrap Headband
    Goodnight Garden Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Feel the Fern Wrap Headband - The Sassy Olive Feel the Fern Wrap Headband - The Sassy Olive
    Feel the Fern Wrap Headband
    Feel the Fern Wrap Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Daphne Floral Wrap Headband - The Sassy Olive Daphne Floral Wrap Headband - The Sassy Olive
    Daphne Floral Wrap Headband
    Daphne Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • It& It&
    It's Just a Phase Stretch Headband
    It's Just a Phase Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Aunt Gatie Floral Stretch - The Sassy Olive Aunt Gatie Floral Stretch - The Sassy Olive
    Aunt Gatie Floral Stretch Headband
    Aunt Gatie Floral Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Simple Suns Stretch - The Sassy Olive Simple Suns Stretch - The Sassy Olive
    Simple Suns Stretch Headband
    Simple Suns Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Breaker Bandana Stretch Headband - The Sassy Olive Breaker Bandana Stretch Headband - The Sassy Olive
    Breaker Bandana Paisley Stretch Headband
    Breaker Bandana Paisley Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Monarch Garden Stretch Headband - The Sassy Olive Monarch Garden Stretch Headband - The Sassy Olive
    Monarch Garden Stretch Headband
    Monarch Garden Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Lucy& Lucy&
    Lucy's Pals Stretch Headband
    Lucy's Pals Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Camo Camo Camo Stretch Headband - The Sassy Olive Camo Camo Camo Stretch - The Sassy Olive
    Woodland Camo Stretch Headband
    Woodland Camo Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Anais Floral Stretch Headband - The Sassy Olive Anais Floral Stretch Headband - The Sassy Olive
    Anais Floral Stretch Headband
    Anais Floral Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Maiden Mauve Stretch Headband - The Sassy Olive Maiden Mauve Stretch Headband - The Sassy Olive
    Maiden Mauve Stretch Headband
    Maiden Mauve Stretch Headband
    Regular price
    $15.00
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    $15.00
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