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The Sassy OliveThe Sassy Olive
  • Shop
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    • Stretch Headbands
    • Top Knot Headbands
    • Wrap Headbands
    • Twist Headbands
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    • Slouchy Beanies
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    • Minimal
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    • Whimsical Cottagecore
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    • Groovy
    Special Offers
    • The Sassy "Style Me" Box
    • Grab Bags
    • Bundle Deals
    • Gift Card
    • Sale
  • Customize
    • Personalize & Pet Face
    • Custom Headbands
    • Special Request Product
    • Custom Fabric Printing
  • Styling
    • Stretch
    • Wrap
    • Top Knot
    • Twist
    • Short Hair
    • Headbands with Bangs
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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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1590 products
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1590 products

  • Emerald Tie Dye Stretch Headband - The Sassy Olive Emerald Tie Dye Stretch Headband - The Sassy Olive
    Emerald Tie Dye Stretch Headband
    Emerald Tie Dye Stretch Headband
    Regular price
    $15.00
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    Sale price
    $15.00
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  • Mellow Blue Floral Stretch Headband - The Sassy Olive Mellow Blue Floral Stretch Headband - The Sassy Olive
    Mellow Blue Floral Stretch Headband
    Mellow Blue Floral Stretch Headband
    Regular price
    $15.00
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    Sale price
    $15.00
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  • I& I&
    I'm a Succa for You Wrap Headband
    I'm a Succa for You Wrap Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Navy Blue Solid Wrap Headband - The Sassy Olive Navy Blue Solid Wrap Headband - The Sassy Olive
    Navy Blue Solid Wrap Headband
    Navy Blue Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Fishing in Michigan Stretch Headband - The Sassy Olive Fishing in Michigan Stretch Headband - The Sassy Olive
    Fishing in Michigan Stretch Headband
    Fishing in Michigan Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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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  • Forte Stretch Headband - The Sassy Olive Forte Stretch Headband - The Sassy Olive
    Forte Stretch Headband
    Forte Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mud on my Jeep Tires Stretch Headband - The Sassy Olive Mud on my Jeep Tires Stretch Headband - The Sassy Olive
    Mud on my Jeep Tires Stretch Headband
    Mud on my Jeep Tires Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $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
    Regular price
    Sale price
    $15.00
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  • Vet Clinic Stretch Headband - The Sassy Olive Vet Clinic Stretch Headband - The Sassy Olive
    Vet Clinic Stretch Headband
    Vet Clinic Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Black Lab Stretch Headband - The Sassy Olive Black Lab Stretch Headband - The Sassy Olive
    Black Lab Stretch Headband
    Black Lab Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Airstream Stretch Headband - The Sassy Olive Airstream Stretch Headband - The Sassy Olive
    Airstream Stretch Headband
    Airstream Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Midnight Bloom Stretch Headband - The Sassy Olive Midnight Bloom Stretch Headband - The Sassy Olive
    Midnight Bloom Stretch Headband
    Midnight Bloom Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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    Sold out
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  • Dog Mom Stretch Headband - The Sassy Olive Dog Mom Stretch Headband - The Sassy Olive
    Dog Mom Stretch Headband
    Dog Mom Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Retro Pink Flower Stretch Headband - The Sassy Olive Retro Pink Flower Stretch Headband - The Sassy Olive
    Retro Pink Flower Stretch Headband
    Retro Pink Flower Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
    Regular price
    $15.00
    Regular price
    Sale price
    $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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  • Flamingling Stretch Headband - The Sassy Olive Flamingling Stretch Headband - The Sassy Olive
    Flamingling Stretch Headband
    Flamingling Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Purple and White Stretch Headband - The Sassy Olive Purple and White Stretch Headband - The Sassy Olive
    Purple and White Stretch Headband
    Purple and White Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Prunella Floral Stretch Headband - The Sassy Olive Prunella Floral Stretch Headband - The Sassy Olive
    Prunella Floral Stretch Headband
    Prunella Floral Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Shamrock Stretch Headband - The Sassy Olive Shamrock Stretch Headband - The Sassy Olive
    Shamrock Stretch Headband
    Shamrock Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Tribbiani Michigan Stretch Headband - The Sassy Olive Tribbiani Michigan Stretch Headband - The Sassy Olive
    Tribbiani Michigan Stretch Headband
    Tribbiani Michigan Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Colorful Caps Stretch Headband - The Sassy Olive Colorful Caps Stretch Headband - The Sassy Olive
    Colorful Caps Stretch Headband
    Colorful Caps Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Daisy Delight Stretch Headband - The Sassy Olive Daisy Delight Stretch Headband - The Sassy Olive
    Daisy Delight Stretch Headband
    Daisy Delight Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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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
    Add to cart
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  • Classic Tie Dye Stretch Headband - The Sassy Olive Classic Tie Dye Stretch Headband - The Sassy Olive
    Classic Tie Dye Stretch Headband
    Classic Tie Dye Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Tuns of Suns Stretch Headband - The Sassy Olive Tuns of Suns Stretch Headband - The Sassy Olive
    Tuns of Suns Stretch Headband
    Tuns of Suns Stretch Headband
    Regular price
    $15.00
    Regular price
    $12.00
    Sale price
    $15.00
    Add to cart
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  • Canna Clinic OG Stretch Headband - The Sassy Olive Canna Clinic OG Stretch Headband - The Sassy Olive
    Canna Clinic OG Stretch Headband
    Canna Clinic OG Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Bright Boho Spring Stretch Headband - The Sassy Olive Bright Boho Spring Stretch Headband - The Sassy Olive
    Bright Boho Spring Stretch Headband
    Bright Boho Spring Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Breaker Bandana Paisley Stretch Headband - The Sassy Olive Breaker Bandana Paisley Stretch Headband - The Sassy Olive
    Breaker Bandana Paisley Stretch Headband
    Breaker Bandana Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Deadtist Appointment Stretch Headband - The Sassy Olive Deadtist Appointment Stretch Headband - The Sassy Olive
    Deadtist Appointment Stretch Headband
    Deadtist Appointment Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Pink Leopard Stretch Headband - The Sassy Olive Pink Leopard Stretch Headband - The Sassy Olive
    Pink Leopard Stretch Headband
    Pink Leopard Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • The Occult Stretch Headband - The Sassy Olive The Occult Stretch Headband - The Sassy Olive
    The Occult Stretch Headband
    The Occult Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Cactus Cuervo Stretch Headband - The Sassy Olive Cactus Cuervo Stretch Headband - The Sassy Olive
    Cactus Cuervo Stretch Headband
    Cactus Cuervo Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Ultrasound Tech Top Knot Headband - The Sassy Olive Ultrasound Tech Top Knot Headband - The Sassy Olive
    Ultrasound Tech Top Knot Headband
    Ultrasound Tech Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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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
    Sale price
    $18.00
    Add to cart
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  • Medici Floral Twist Headband - The Sassy Olive Medici Floral Twist Headband - The Sassy Olive
    Medici Floral Twist Headband
    Medici Floral Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Bait Shop Stretch Headband - The Sassy Olive Bait Shop Stretch Headband - The Sassy Olive
    Bait Shop Stretch Headband
    Bait Shop Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Simple Suns Stretch Headband - The Sassy Olive Simple Suns Stretch Headband - The Sassy Olive
    Simple Suns Stretch Headband
    Simple Suns Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Floofs Stretch Headband - The Sassy Olive Floofs Stretch Headband - The Sassy Olive
    Floofs Stretch Headband
    Floofs Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Afternoon with Ethel Stretch Headband - The Sassy Olive Afternoon with Ethel Stretch Headband - The Sassy Olive
    Afternoon with Ethel Stretch Headband
    Afternoon with Ethel Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Mushroom Love Scrunchie Pack - The Sassy Olive Mushroom Love Scrunchie Pack - The Sassy Olive
    Mushroom Love Scrunchie Pack
    Mushroom Love Scrunchie Pack
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • I Don& I Don&
    I Don't Carrot All Stretch Headband
    I Don't Carrot All Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Happy Camper Stretch Headband - The Sassy Olive Happy Camper Stretch Headband - The Sassy Olive
    Happy Camper Stretch Headband
    Happy Camper Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Moroccan Summer Wrap Headband - The Sassy Olive Moroccan Summer Wrap Headband - The Sassy Olive
    Moroccan Summer Wrap Headband
    Moroccan Summer Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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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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  • All the Cell Things Stretch Headband - The Sassy Olive All the Cell Things Stretch Headband - The Sassy Olive
    All the Cell Things Stretch Headband
    All the Cell Things Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Prison Mike Stretch Headband - The Sassy Olive Prison Mike Stretch Headband - The Sassy Olive
    Prison Mike Stretch Headband
    Prison Mike Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Tooled Leather Stretch Headband - The Sassy Olive Tooled Leather Stretch Headband - The Sassy Olive
    Tooled Leather Stretch Headband
    Tooled Leather Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Bohemian at Heart Stretch Headband - The Sassy Olive Bohemian at Heart Stretch Headband - The Sassy Olive
    Bohemian at Heart Stretch Headband
    Bohemian at Heart Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Joy Luxe Stretch Headband - The Sassy Olive Joy Luxe Stretch Headband - The Sassy Olive
    Joy Luxe Stretch Headband
    Joy Luxe Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Skulls n Roses Stretch Headband - The Sassy Olive Skulls n Roses Stretch Headband - The Sassy Olive
    Skulls n Roses Stretch Headband
    Skulls n Roses Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • It& It&
    It's Just a Phase Stretch Headband
    It's Just a Phase Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • PIVOT Stretch Headband - The Sassy Olive PIVOT Stretch Headband - The Sassy Olive
    PIVOT Stretch Headband
    PIVOT Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Piggy Pig Stretch Headband - The Sassy Olive Piggy Pig Stretch Headband - The Sassy Olive
    Piggy Pig Stretch Headband
    Piggy Pig Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Butterflies Wrap Headband - The Sassy Olive Butterflies Wrap Headband - The Sassy Olive
    Butterflies Wrap Headband
    Butterflies Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Sandworm Stretch Headband - The Sassy Olive Sandworm Stretch Headband - The Sassy Olive
    Sandworm Stretch Headband
    Sandworm 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
    Regular price
    Sale price
    $15.00
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  • What& What&
    What's On the Inside Stretch Headband
    What's On the Inside Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Breezy Boho Floral Wrap Headband - The Sassy Olive Breezy Boho Floral Wrap Headband - The Sassy Olive
    Breezy Boho Floral Wrap Headband
    Breezy Boho Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Stevie Floral Wrap Headband - The Sassy Olive Stevie Floral Wrap Headband - The Sassy Olive
    Stevie Floral Wrap Headband
    Stevie Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Tranquil Tie Dye Stretch Headband - The Sassy Olive Tranquil Tie Dye Stretch Headband - The Sassy Olive
    Tranquil Tie Dye Stretch Headband
    Tranquil Tie Dye Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Dragonfly Stretch Headband - The Sassy Olive Dragonfly Stretch Headband - The Sassy Olive
    Dragonfly Stretch Headband
    Dragonfly Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Atrium Stretch Headband - The Sassy Olive Atrium Stretch Headband - The Sassy Olive
    Atrium Stretch Headband
    Atrium Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Maybe It& Maybe It&
    Maybe It's Neighbelline Stretch Headband
    Maybe It's Neighbelline Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Owls Give a Hoot Stretch Headband - The Sassy Olive Owls Give a Hoot Stretch Headband - The Sassy Olive
    Owls Give a Hoot Stretch Headband
    Owls Give a Hoot Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Black and Red Stretch Headband - The Sassy Olive Black and Red Stretch Headband - The Sassy Olive
    Black and Red Stretch Headband
    Black and Red Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Call the WAAambulance Stretch Headband - The Sassy Olive Call the WAAambulance Stretch Headband - The Sassy Olive
    Call the WAAambulance Stretch Headband
    Call the WAAambulance Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Tia Mauve Solid Wrap Headband Tia Mauve Solid Wrap Headband
    Tia Mauve Solid Wrap Headband
    Tia Mauve Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Izzo Michigan State Stretch Headband - The Sassy Olive Izzo Michigan State Stretch Headband - The Sassy Olive
    Izzo Michigan State Stretch Headband
    Izzo Michigan State Stretch Headband
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  • Vintage Detroit Football Stretch Headband - The Sassy Olive Vintage Detroit Football Stretch Headband - The Sassy Olive
    Vintage Detroit Football Stretch Headband
    Vintage Detroit Football Stretch Headband
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  • Red Bandana Stretch Headband - The Sassy Olive Red Bandana Stretch Headband - The Sassy Olive
    Red Bandana Stretch Headband
    Red Bandana Stretch Headband
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  • Cassieopia Stretch Headband - The Sassy Olive Cassieopia Stretch Headband - The Sassy Olive
    Cassieopia Stretch Headband
    Cassieopia Stretch Headband
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  • Muddy Jeep Wave Stretch Headband - The Sassy Olive Muddy Jeep Wave Stretch Headband - The Sassy Olive
    Muddy Jeep Wave Stretch Headband
    Muddy Jeep Wave Stretch Headband
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  • Stinging Shores Stretch Headband - The Sassy Olive Stinging Shores Stretch Headband - The Sassy Olive
    Stinging Shores Stretch Headband
    Stinging Shores Stretch Headband
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  • Happy Teeth Stretch Headband - The Sassy Olive Happy Teeth Stretch Headband - The Sassy Olive
    Happy Teeth Stretch Headband
    Happy Teeth Stretch Headband
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  • Heather Grey Solid Stretch Headband - The Sassy Olive Heather Grey Solid Stretch Headband - The Sassy Olive
    Heather Grey Solid Stretch Headband
    Heather Grey Solid Stretch Headband
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  • Barbie& Barbie&
    Barbie's Bandana Paisley Stretch Headband
    Barbie's Bandana Paisley Stretch Headband
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  • Ocean Gray Stretch Headband - The Sassy Olive Ocean Gray Stretch Headband - The Sassy Olive
    Ocean Gray Stretch Headband
    Ocean Gray Stretch Headband
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