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Collection: Preppy Summer Collection

Coastal cool meets everyday cute in the Preppy Summer Collection. These clean, crisp prints bring major beach club energy — think Hamptons chic with handmade flair. Classic bows, lemon tiles, coral reef vibes? Yes please. They’re fresh, fun, and ready to pop with every ponytail and side part.

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  • Sweet Cherry Pie Stretch Headband - The Sassy Olive Sweet Cherry Pie Stretch Headband - The Sassy Olive
    Sweet Cherry Pie Stretch Headband
    Sweet Cherry Pie Stretch Headband
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    $15.00
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  • Watermelon Twist Headband - The Sassy Olive Watermelon Twist Headband - The Sassy Olive
    Watermelon Twist Headband
    Watermelon Twist Headband
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    $18.00
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  • Patch Made in Heaven Stretch Headband - The Sassy Olive Patch Made in Heaven Stretch Headband - The Sassy Olive
    Patch Made in Heaven Stretch Headband
    Patch Made in Heaven Stretch Headband
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  • Garden Finds Stretch Headband - The Sassy Olive Garden Finds Stretch Headband - The Sassy Olive
    Garden Finds Stretch Headband
    Garden Finds Stretch Headband
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  • Watermelon Seeds Stretch Headband - The Sassy Olive Watermelon Seeds Stretch Headband - The Sassy Olive
    Watermelon Seeds Stretch Headband
    Watermelon Seeds Stretch Headband
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    $15.00
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  • Just Peachy Stretch Headband - The Sassy Olive Just Peachy Stretch Headband - The Sassy Olive
    Just Peachy Stretch Headband
    Just Peachy Stretch Headband
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  • Strawberry Garden Stretch Headband - The Sassy Olive Strawberry Garden Stretch Headband - The Sassy Olive
    Strawberry Garden Stretch Headband
    Strawberry Garden Stretch Headband
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  • Spilled Berries Stretch Headband - The Sassy Olive Spilled Berries Stretch Headband - The Sassy Olive
    Spilled Berries Stretch Headband
    Spilled Berries Stretch Headband
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  • Strawberry Babies Stretch Headband - The Sassy Olive Strawberry Babies Stretch Headband - The Sassy Olive
    Strawberry Babies Stretch Headband
    Strawberry Babies Stretch Headband
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    $15.00
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  • Pink Drink Stretch - The Sassy Olive Pink Drink Stretch - The Sassy Olive
    Pink Drink Stretch Headband
    Pink Drink Stretch Headband
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    $15.00
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  • Cherries Blossoms Stretch Headband - The Sassy Olive Cherries Blossoms Stretch - The Sassy Olive
    Cherries Blossoms Stretch Headband
    Cherries Blossoms Stretch Headband
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    $15.00
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  • I Cherry-ish You Stretch Headband - The Sassy Olive I Cherry-ish You Stretch - The Sassy Olive
    I Cherry-ish You Stretch Headband
    I Cherry-ish You Stretch Headband
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