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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

  • E&E Stretch Headband - The Sassy Olive E&E Stretch Headband - The Sassy Olive
    E&E Stretch Headband
    E&E Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Stargazing with Vincent Wrap Headband - The Sassy Olive Stargazing with Vincent Wrap Headband - The Sassy Olive
    Stargazing with Vincent Wrap Headband
    Stargazing with Vincent Wrap Headband
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    $18.00
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    $18.00
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  • Hop to It Stretch Headband - The Sassy Olive Hop to It Stretch Headband - The Sassy Olive
    Hop to It Stretch Headband
    Hop to It Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Fur Friends Stretch Headband - The Sassy Olive Fur Friends Stretch Headband - The Sassy Olive
    Fur Friends Stretch Headband
    Fur Friends Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Galaxy Gamer Stretch Headband - The Sassy Olive Galaxy Gamer Stretch Headband - The Sassy Olive
    Galaxy Gamer Stretch Headband
    Galaxy Gamer Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Breaker Bandana Wrap Headband - The Sassy Olive Breaker Bandana Wrap Headband - The Sassy Olive
    Breaker Bandana Paisley Wrap Headband
    Breaker Bandana Paisley Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Basic Roses Wrap Headband - The Sassy Olive Basic Roses Wrap Headband - The Sassy Olive
    Basic Roses Wrap Headband
    Basic Roses Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Hidden Owl Wrap Headband - The Sassy Olive Hidden Owl Wrap Headband - The Sassy Olive
    Hidden Owl Wrap Headband
    Hidden Owl Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • NuKaci Wrap Headband - The Sassy Olive NuKaci Wrap Headband - The Sassy Olive
    NuKaci Wrap Headband
    NuKaci Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Dino Nuggies Stretch Headband - The Sassy Olive Dino Nuggies Stretch Headband - The Sassy Olive
    Dino Nuggies Stretch Headband
    Dino Nuggies Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Pickleball Everyday Stretch Headband - The Sassy Olive Pickleball Everyday Stretch Headband - The Sassy Olive
    Pickleball Everyday Stretch Headband
    Pickleball Everyday Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Pateast Paisley Top Knot Headband - The Sassy Olive Pateast Paisley Top Knot Headband - The Sassy Olive
    Pateast Paisley Top Knot Headband
    Pateast Paisley Top Knot Headband
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    $15.00
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    $15.00
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