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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

  • Flower Glade Wrap Headband - The Sassy Olive Flower Glade Wrap Headband - The Sassy Olive
    Flower Glade Wrap Headband
    Flower Glade Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Fire Fighter Stretch - The Sassy Olive Fire Fighter Stretch - The Sassy Olive
    Firefighter Stretch Headband
    Firefighter Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Women of History Stretch Headband - The Sassy Olive Women of History Stretch Headband - The Sassy Olive
    Women of History Stretch Headband
    Women of History Stretch Headband
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    $15.00
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    $15.00
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  • Classic Leopard Print Stretch Headband - The Sassy Olive Classic Leopard Print Stretch Headband - The Sassy Olive
    Classic Leopard Print Stretch Headband
    Classic Leopard Print Stretch Headband
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    $15.00
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    $15.00
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  • Tommy& Tommy&
    Tommy's Donuts Stretch Headband
    Tommy's Donuts Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • D&D Dice Stretch Headband - The Sassy Olive D&D Dice Stretch Headband - The Sassy Olive
    D&D Dice Stretch Headband
    D&D Dice Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Limited Edition Stretch Headband - The Sassy Olive Limited Edition Stretch Headband - The Sassy Olive
    Limited Edition Stretch Headband
    Limited Edition Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Special Delivery Stretch Headband - The Sassy Olive Special Delivery Stretch Headband - The Sassy Olive
    Special Delivery Stretch Headband
    Special Delivery Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Breezy Boho Floral Wrap - The Sassy Olive Breezy Boho Floral Wrap - The Sassy Olive
    Breezy Boho Floral Wrap Headband
    Breezy Boho Floral Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Bell Bottoms Retro Floral Stretch Headband - The Sassy Olive Bell Bottoms Retro Floral Stretch Headband - The Sassy Olive
    Bell Bottoms Retro Floral Stretch Headband
    Bell Bottoms Retro Floral Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Arizona Blue Floral Stretch Headband - The Sassy Olive Arizona Blue Floral Stretch Headband - The Sassy Olive
    Arizona Blue Floral Stretch Headband
    Arizona Blue Floral Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Leighton Wrap Headband - The Sassy Olive Leighton Wrap Headband - The Sassy Olive
    Leighton Wrap Headband
    Leighton Wrap Headband
    Regular price
    $18.00
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    $18.00
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