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    Special Offers
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    • Grab Bags
    • Bundle Deals
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    • Personalize & Pet Face
    • Custom Headbands
    • Special Request Product
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Collection: All Products

Handmade stretch headbands in every style and pattern. Sort by style or pattern type to find your perfect fit — all soft, comfy, and sewn in Michigan.
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1542 products
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1542 products

  • Joy Luxe Boho Buff - The Sassy Olive Joy Luxe Boho Buff - The Sassy Olive
    Joy Luxe Boho Buff
    Joy Luxe Boho Buff
    Regular price
    $18.00
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    Sale price
    $18.00
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  • Monarch Flights Stretch Headband - The Sassy Olive Monarch Flights Stretch Headband - The Sassy Olive
    Monarch Flights Stretch Headband
    Monarch Flights Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Monarch Flights Boho Buff - The Sassy Olive Monarch Flights Boho Buff - The Sassy Olive
    Monarch Flights Boho Buff
    Monarch Flights Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Strawberry Plant Stretch Headband - The Sassy Olive Strawberry Plant Stretch Headband - The Sassy Olive
    Strawberry Plant Stretch Headband
    Strawberry Plant Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Strawberry Plant Wrap Headband - The Sassy Olive Strawberry Plant Wrap Headband - The Sassy Olive
    Strawberry Plant Wrap Headband
    Strawberry Plant Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Strawberry Plant Boho Buff - The Sassy Olive Strawberry Plant Boho Buff - The Sassy Olive
    Strawberry Plant Boho Buff
    Strawberry Plant Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $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
    Sale price
    $15.00
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  • Witchy Night Boho Buff - The Sassy Olive Witchy Night Boho Buff - The Sassy Olive
    Witchy Night Boho Buff
    Witchy Night Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Witchy Night Wrap Headband - The Sassy Olive Witchy Night Wrap Headband - The Sassy Olive
    Witchy Night Wrap Headband
    Witchy Night Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Lotus Bloom Twist Headband - The Sassy Olive Lotus Bloom Twist Headband - The Sassy Olive
    Lotus Bloom Twist Headband
    Lotus Bloom Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Daphne Twist Headband - The Sassy Olive Daphne Twist Headband - The Sassy Olive
    Daphne Twist Headband
    Daphne Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Moroccan Summer Twist Headband - The Sassy Olive Moroccan Summer Twist Headband - The Sassy Olive
    Moroccan Summer Twist Headband
    Moroccan Summer Twist Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Tooled Leather Twist Headband - The Sassy Olive Tooled Leather Twist Headband - The Sassy Olive
    Tooled Leather Twist Headband
    Tooled Leather Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Charmeuse Stretch Satin by the Yard - The Sassy Olive Charmeuse Stretch Satin by the Yard - The Sassy Olive
    Polysatin by the Yard
    Polysatin by the Yard
    Regular price
    $24.00
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    $24.00
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  • Cotton Broadcloth by the Yard - The Sassy Olive Cotton Broadcloth by the Yard - The Sassy Olive
    Cotton Broadcloth Woven by the Yard
    Cotton Broadcloth Woven by the Yard
    Regular price
    $15.00
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    $15.00
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  • Dancing Skeletons Stretch Headband - The Sassy Olive Dancing Skeletons Stretch Headband - The Sassy Olive
    Dancing Skeletons Stretch Headband
    Dancing Skeletons Stretch Headband
    Regular price
    $15.00
    Regular price
    $12.00
    Sale price
    $15.00
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  • New Order Stretch Headband - The Sassy Olive New Order Stretch Headband - The Sassy Olive
    New Order Stretch Headband
    New Order Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • New Order Wrap Headband - The Sassy Olive New Order Wrap Headband - The Sassy Olive
    New Order Wrap Headband
    New Order Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Shelves of Spells Stretch Headband - The Sassy Olive Shelves of Spells Stretch Headband - The Sassy Olive
    Shelves of Spells Stretch Headband
    Shelves of Spells Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Acorn Boho Buff - The Sassy Olive Acorn Boho Buff - The Sassy Olive
    Acorn Boho Buff
    Acorn Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Basic Roses Boho Buff - The Sassy Olive Basic Roses Boho Buff - The Sassy Olive
    Basic Roses Boho Buff
    Basic Roses Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Basic Roses Stretch Headband - The Sassy Olive Basic Roses Stretch Headband - The Sassy Olive
    Basic Roses Stretch Headband
    Basic Roses Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Basic Roses Top Knot Headband - The Sassy Olive Basic Roses Top Knot Headband - The Sassy Olive
    Basic Roses Top Knot Headband
    Basic Roses Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Basic Roses Twist Headband - The Sassy Olive Basic Roses Twist Headband - The Sassy Olive
    Basic Roses Twist Headband
    Basic Roses Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $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
    Regular price
    Sale price
    $18.00
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  • Flower Glade Boho Buff - The Sassy Olive Flower Glade Boho Buff - The Sassy Olive
    Flower Glade Boho Buff
    Flower Glade Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Flower Glade Stretch Headband - The Sassy Olive Flower Glade Stretch Headband - The Sassy Olive
    Flower Glade Stretch Headband
    Flower Glade Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • 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
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Hidden Owl Boho Buff - The Sassy Olive Hidden Owl Boho Buff - The Sassy Olive
    Hidden Owl Boho Buff
    Hidden Owl Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Hidden Owl Stretch Headband - The Sassy Olive Hidden Owl Stretch Headband - The Sassy Olive
    Hidden Owl Stretch Headband
    Hidden Owl Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Hidden Owl Twist Headband - The Sassy Olive Hidden Owl Twist Headband - The Sassy Olive
    Hidden Owl Twist Headband
    Hidden Owl Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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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
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Mushroom Foraging Boho Buff - The Sassy Olive Mushroom Foraging Boho Buff - The Sassy Olive
    Mushroom Foraging Boho Buff
    Mushroom Foraging Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Mushroom Foraging Stretch Headband - The Sassy Olive Mushroom Foraging Stretch Headband - The Sassy Olive
    Mushroom Foraging Stretch Headband
    Mushroom Foraging Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mushroom Foraging Top Knot Headband - The Sassy Olive Mushroom Foraging Top Knot Headband - The Sassy Olive
    Mushroom Foraging Top Knot Headband
    Mushroom Foraging Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Mushroom Foraging Twist Headband - The Sassy Olive Mushroom Foraging Twist Headband - The Sassy Olive
    Mushroom Foraging Twist Headband
    Mushroom Foraging Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Mushroom Foraging Wrap Headband - The Sassy Olive Mushroom Foraging Wrap Headband - The Sassy Olive
    Mushroom Foraging Wrap Headband
    Mushroom Foraging Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • NuKaci Boho Buff - The Sassy Olive NuKaci Boho Buff - The Sassy Olive
    NuKaci Boho Buff
    NuKaci Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • NuKaci Stretch Headband - The Sassy Olive NuKaci Stretch Headband - The Sassy Olive
    NuKaci Stretch Headband
    NuKaci Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • NuKaci Top Knot Headband - The Sassy Olive NuKaci Top Knot Headband - The Sassy Olive
    NuKaci Top Knot Headband
    NuKaci Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Silas Plaid Boho Buff - The Sassy Olive Silas Plaid Boho Buff - The Sassy Olive
    Silas Plaid Boho Buff
    Silas Plaid Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Silas Plaid Stretch Headband - The Sassy Olive Silas Plaid Stretch Headband - The Sassy Olive
    Silas Plaid Stretch Headband
    Silas Plaid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Twiggy Flowers Boho Buff - The Sassy Olive Twiggy Flowers Boho Buff - The Sassy Olive
    Twiggy Flowers Boho Buff
    Twiggy Flowers Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Corn Penguid Sasshole Random Ass Stretch - The Sassy Olive Corn Penguid Sasshole Random Ass Stretch - The Sassy Olive
    Corn Penguid Sasshole Random Ass Stretch Headband
    Corn Penguid Sasshole Random Ass Stretch Headband
    Regular price
    $10.00
    Regular price
    Sale price
    $10.00
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  • Crocs Stretch Headband - The Sassy Olive Crocs Stretch Headband - The Sassy Olive
    Crocs Stretch Headband
    Crocs Stretch Headband
    Regular price
    $10.00
    Regular price
    Sale price
    $10.00
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  • Bernese Mountain Dog Stretch Headband - The Sassy Olive Bernese Mountain Dog Stretch Headband - The Sassy Olive
    Bernese Mountain Dog Stretch Headband
    Bernese Mountain Dog Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Springer Spaniel Stretch Headband - The Sassy Olive Springer Spaniel Stretch Headband - The Sassy Olive
    Springer Spaniel Stretch Headband
    Springer Spaniel Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Wheaten Terrier Stretch Headband - The Sassy Olive Wheaten Terrier Stretch Headband - The Sassy Olive
    Wheaten Terrier Stretch Headband
    Wheaten Terrier Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • ASL Stretch Headband - The Sassy Olive ASL Stretch Headband - The Sassy Olive
    ASL Stretch Headband
    ASL Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Bloody Mary Stretch Headband - The Sassy Olive Bloody Mary Stretch Headband - The Sassy Olive
    Bloody Mary Stretch Headband
    Bloody Mary Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $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
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Goatin& Goatin&
    Goatin' Around Stretch Headband
    Goatin' Around Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Dairy Cow Stretch Headband - The Sassy Olive Dairy Cow Stretch Headband - The Sassy Olive
    Dairy Cow Stretch Headband
    Dairy Cow Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • I Hate People Stretch Headband - The Sassy Olive I Hate People Stretch Headband - The Sassy Olive
    I Hate People Stretch Headband
    I Hate People Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Avocado Stretch Headband - The Sassy Olive Avocado Stretch Headband - The Sassy Olive
    Avocado Stretch Headband
    Avocado Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • October Third Stretch Headband - The Sassy Olive October Third Stretch Headband - The Sassy Olive
    October Third Stretch Headband
    October Third Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Cactus Stretch Headband - The Sassy Olive Cactus Stretch Headband - The Sassy Olive
    Cactus Stretch Headband
    Cactus Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $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
    Regular price
    Sale price
    $15.00
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  • Purple Galaxy Stretch Headband - The Sassy Olive Purple Galaxy Stretch Headband - The Sassy Olive
    Purple Galaxy Stretch Headband
    Purple Galaxy Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Walter Stretch Headband - The Sassy Olive Walter Stretch Headband - The Sassy Olive
    Walter Stretch Headband
    Walter Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Why So Sheepish Stretch Headband - The Sassy Olive Why So Sheepish Stretch Headband - The Sassy Olive
    Why So Sheepish Stretch Headband
    Why So Sheepish Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Dragon Croissant Pumpkin Toadlet Random Ass Stretch - The Sassy Olive Dragon Croissant Pumpkin Toadlet Random Ass Stretch - The Sassy Olive
    Dragon Croissant Pumpkin Toadlet Random Ass Stretch Headband
    Dragon Croissant Pumpkin Toadlet Random Ass Stretch Headband
    Regular price
    $10.00
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    $10.00
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  • Wishbone 4 Stretch Headband - The Sassy Olive Wishbone 4 Stretch Headband - The Sassy Olive
    Wishbone 4 Stretch Headband
    Wishbone 4 Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • 60& 60&
    60's Picnic Blanket Boho Buff
    60's Picnic Blanket Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • 60& 60&
    60's Picnic Blanket Stretch Headband
    60's Picnic Blanket Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • 60& 60&
    60's Picnic Blanket Wrap Headband
    60's Picnic Blanket Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Bell Bottoms Retro Floral Boho Buff - The Sassy Olive Bell Bottoms Retro Floral Boho Buff - The Sassy Olive
    Bell Bottoms Retro Floral Boho Buff
    Bell Bottoms Retro Floral Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $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
    Regular price
    Sale price
    $15.00
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  • Bell Bottoms Retro Floral Wrap Headband - The Sassy Olive Bell Bottoms Retro Floral Wrap Headband - The Sassy Olive
    Bell Bottoms Retro Floral Wrap Headband
    Bell Bottoms Retro Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Chatty Cathy Stretch Headband - The Sassy Olive Chatty Cathy Stretch Headband - The Sassy Olive
    Chatty Cathy Stretch Headband
    Chatty Cathy Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mod Girl Vintage Floral Boho Buff - The Sassy Olive Mod Girl Vintage Floral Boho Buff - The Sassy Olive
    Mod Girl Vintage Floral Boho Buff
    Mod Girl Vintage Floral Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Mod Girl Vintage Floral Stretch Headband - The Sassy Olive Mod Girl Vintage Floral Stretch Headband - The Sassy Olive
    Mod Girl Vintage Floral Stretch Headband
    Mod Girl Vintage Floral Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mod Girl Vintage Floral Wrap Headband - The Sassy Olive Mod Girl Vintage Floral Wrap Headband - The Sassy Olive
    Mod Girl Vintage Floral Wrap Headband
    Mod Girl Vintage Floral Wrap Headband
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  • Sixties Gardens Boho Buff - The Sassy Olive Sixties Gardens Boho Buff - The Sassy Olive
    Sixties Gardens Boho Buff
    Sixties Gardens Boho Buff
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  • Sixties Gardens Stretch Headband - The Sassy Olive Sixties Gardens Stretch Headband - The Sassy Olive
    Sixties Gardens Stretch Headband
    Sixties Gardens Stretch Headband
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  • The Beatles Boho Buff - The Sassy Olive The Beatles Boho Buff - The Sassy Olive
    The Beatles Boho Buff
    The Beatles Boho Buff
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  • The Beatles Stretch Headband - The Sassy Olive The Beatles Stretch Headband - The Sassy Olive
    The Beatles Stretch Headband
    The Beatles Stretch Headband
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  • The Beatles Wrap Headband - The Sassy Olive The Beatles Wrap Headband - The Sassy Olive
    The Beatles Wrap Headband
    The Beatles Wrap Headband
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  • Pothole Dinosaur Marshmallow Random Ass Stretch - The Sassy Olive Pothole Dinosaur Marshmallow Random Ass Stretch - The Sassy Olive
    Pothole Dinosaur Marshmallow Random Ass Stretch Headband
    Pothole Dinosaur Marshmallow Random Ass Stretch Headband
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    $10.00
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  • Banana Yellow Solid Stretch Headband - The Sassy Olive Banana Yellow Solid Stretch Headband - The Sassy Olive
    Banana Yellow Solid Stretch Headband
    Banana Yellow Solid Stretch Headband
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