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The Sassy OliveThe Sassy Olive
  • Shop
    Featured Collections
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    • Shop All Collections
    Shop by Type
    • Stretch Headbands
    • Top Knot Headbands
    • Wrap Headbands
    • Twist Headbands
    • Boho Buff
    • Slouchy Beanies
    • Benzie Caps
    • Scrunchie Packs
    • All Styles
    Shop by Pattern
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    • Paisley
    • Solid Colors
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    • Tie Dye
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    Shop by Vibe
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    • Outdoorsy
    • Trendy
    • Y2K
    • Athletic
    • Minimal
    • Girly
    • Whimsical Cottagecore
    • Punk
    • Spooky
    • 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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Cart

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

  • Inkwell Paisley Wrap Headband - The Sassy Olive Inkwell Paisley Wrap Headband - The Sassy Olive
    Inkwell Paisley Wrap Headband
    Inkwell Paisley Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Dollhouse Paisley Stretch Headband - The Sassy Olive Dollhouse Paisley Stretch Headband - The Sassy Olive
    Dollhouse Paisley Stretch Headband
    Dollhouse Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Blush Pink Solid Stretch Headband - The Sassy Olive Blush Pink Solid Stretch Headband - The Sassy Olive
    Blush Pink Solid Stretch Headband
    Blush Pink Solid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Hawaiian Blue Solid Wrap Headband - The Sassy Olive Hawaiian Blue Solid Wrap Headband - The Sassy Olive
    Hawaiian Blue Solid Wrap Headband
    Hawaiian Blue Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Boot Scootin Stretch Headband - The Sassy Olive Boot Scootin Stretch Headband - The Sassy Olive
    Boot Scootin Stretch Headband
    Boot Scootin Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Red Mandala Love Wrap Headband - The Sassy Olive Red Mandala Love Wrap Headband - The Sassy Olive
    Red Mandala Love Wrap Headband
    Red Mandala Love Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Mod Pastel Flowers Wrap Headband - The Sassy Olive Mod Pastel Flowers Wrap Headband - The Sassy Olive
    Mod Pastel Flowers Wrap Headband
    Mod Pastel Flowers Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Violet Veins Wrap Headband - The Sassy Olive Violet Veins Wrap Headband - The Sassy Olive
    Violet Veins Wrap Headband
    Violet Veins Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Garnet Grove Stretch Headband - The Sassy Olive Garnet Grove Stretch Headband - The Sassy Olive
    Garnet Grove Stretch Headband
    Garnet Grove Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sea Garden Blue Stretch Headband - The Sassy Olive Sea Garden Blue Stretch Headband - The Sassy Olive
    Sea Garden Blue Stretch Headband
    Sea Garden Blue Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Victoria’s Pink Polka Dot Stretch Headband - The Sassy Olive Victoria’s Pink Polka Dot Stretch Headband - The Sassy Olive
    Victoria’s Pink Polka Dot Stretch Headband
    Victoria’s Pink Polka Dot Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Classic Black Polka Dot Top Knot Headband Classic Black Polka Dot Top Knot Headband - The Sassy Olive
    Classic Black Polka Dot Top Knot Headband
    Classic Black Polka Dot Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Miss Piggy Scrunchie Pack - The Sassy Olive Miss Piggy Scrunchie Pack - The Sassy Olive
    Miss Piggy Scrunchie Pack
    Miss Piggy Scrunchie Pack
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Bram Plaid Wrap Headband - The Sassy Olive Bram Plaid Wrap Headband - The Sassy Olive
    Bram Plaid Wrap Headband
    Bram Plaid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Hello Henna Wrap Headband - The Sassy Olive Hello Henna Wrap Headband - The Sassy Olive
    Hello Henna Wrap Headband
    Hello Henna Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Monarch Garden Wrap Headband - The Sassy Olive Monarch Garden Wrap Headband - The Sassy Olive
    Monarch Garden Wrap Headband
    Monarch Garden Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Cow Print Black and White Wrap Headband - The Sassy Olive Cow Print Black and White Wrap Headband - The Sassy Olive
    Cow Print Black and White Wrap Headband
    Cow Print Black and White Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Live, Laugh, Leopard Print Wrap Headband - The Sassy Olive Live, Laugh, Leopard Print Wrap Headband - The Sassy Olive
    Live, Laugh, Leopard Print Wrap Headband
    Live, Laugh, Leopard Print Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Lilac Purple Solid Wrap Headband - The Sassy Olive Lilac Purple Solid Wrap Headband - The Sassy Olive
    Lilac Purple Solid Wrap Headband
    Lilac Purple Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • The Queen’s Garden Olive Twist Headband - The Sassy Olive The Queen’s Garden Olive Twist Headband - The Sassy Olive
    The Queen’s Garden Olive Twist Headband
    The Queen’s Garden Olive Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Little White Flowers Twist Headband - The Sassy Olive Little White Flowers Twist Headband - The Sassy Olive
    Little White Flowers Twist Headband
    Little White Flowers Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Eva Floral Twist Headband - The Sassy Olive Eva Floral Twist Headband - The Sassy Olive
    Eva Floral Twist Headband
    Eva Floral Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Chocolate Garden Topknot Headband - The Sassy Olive Chocolate Garden Topknot Headband - The Sassy Olive
    Chocolate Garden Topknot Headband
    Chocolate Garden Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Daisy Delight Topknot Headband - The Sassy Olive Daisy Delight Topknot Headband - The Sassy Olive
    Daisy Delight Topknot Headband
    Daisy Delight Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Eggplant Purple Top Knot Headband - The Sassy Olive Eggplant Purple Top Knot Headband - The Sassy Olive
    Eggplant Purple Top Knot Headband
    Eggplant Purple Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Strawberry Milk Pink Solid Top Knot Headband Strawberry Milk Pink Solid Top Knot Headband
    Strawberry Milk Pink Solid Top Knot Headband
    Strawberry Milk Pink Solid Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Calathea Twist Headband - The Sassy Olive Calathea Twist Headband - The Sassy Olive
    Calathea Twist Headband
    Calathea Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Pinecone Party Stretch Headband - The Sassy Olive Pinecone Party Stretch Headband - The Sassy Olive
    Pinecone Party Stretch Headband
    Pinecone Party Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Starlit Woods Stretch Headband - The Sassy Olive Starlit Woods Stretch Headband - The Sassy Olive
    Starlit Woods Stretch Headband
    Starlit Woods Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • T - rexmas Cookies Stretch Headband - The Sassy Olive T - rexmas Cookies Stretch Headband - The Sassy Olive
    T-rexmas Cookies Stretch Headband
    T-rexmas Cookies Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
    Add to cart
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  • X - rays Stretch Headband - The Sassy Olive X - rays Stretch Headband - The Sassy Olive
    X-rays Stretch Headband
    X-rays Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Monstera Top Knot Headband - The Sassy Olive Monstera Top Knot Headband - The Sassy Olive
    Monstera Top Knot Headband
    Monstera Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Woolly Worm Stretch Headband - The Sassy Olive Woolly Worm Stretch Headband - The Sassy Olive
    Woolly Worm Stretch Headband
    Woolly Worm Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
    Add to cart
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  • Domestic Violence Awareness Stretch Headband - The Sassy Olive Domestic Violence Awareness Stretch Headband - The Sassy Olive
    Purple Ribbon Stretch Headband
    Purple Ribbon Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Reynolds Stretch Headband - The Sassy Olive Reynolds Stretch Headband - The Sassy Olive
    Reynolds Stretch Headband
    Reynolds Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Cocktail Shrimp Stretch Headband - The Sassy Olive Cocktail Shrimp Stretch Headband - The Sassy Olive
    Cocktail Shrimp Stretch Headband
    Cocktail Shrimp Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Blueberry Lemon Squeeze Stretch Headband - The Sassy Olive Blueberry Lemon Squeeze Stretch Headband - The Sassy Olive
    Blueberry Lemon Squeeze Stretch Headband
    Blueberry Lemon Squeeze Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Spirits of Spring Stretch Headband - The Sassy Olive Midnight Bloom Stretch Headband - The Sassy Olive
    Spirits of Spring Stretch Headband
    Spirits of Spring Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Oh Whale Stretch Headband - The Sassy Olive Oh Whale Stretch Headband - The Sassy Olive
    Oh Whale Stretch Headband
    Oh Whale Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Silhouette Stretch Headband - The Sassy Olive Silhouette Stretch Headband - The Sassy Olive
    Silhouette Stretch Headband
    Silhouette Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • French Bulldog Stretch Headband - The Sassy Olive French Bulldog Stretch Headband - The Sassy Olive
    French Bulldog Stretch Headband
    French Bulldog Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Alphabet Scramble Stretch Headband - The Sassy Olive Alphabet Scramble Stretch Headband - The Sassy Olive
    Alphabet Scramble Stretch Headband
    Alphabet Scramble Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Border Collie Stretch Headband - The Sassy Olive Border Collie Stretch Headband - The Sassy Olive
    Border Collie Stretch Headband
    Border Collie Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Lead Jammer Stretch Headband - The Sassy Olive Lead Jammer Stretch Headband - The Sassy Olive
    Lead Jammer Stretch Headband
    Lead Jammer Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Climb Red Stretch Headband - The Sassy Olive Climb Red Stretch Headband - The Sassy Olive
    Climb Red Stretch Headband
    Climb Red Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Gaston Stretch Headband - The Sassy Olive Gaston Stretch Headband - The Sassy Olive
    Gaston Stretch Headband
    Gaston Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Downhill Stretch Headband - The Sassy Olive Downhill Stretch Headband - The Sassy Olive
    Downhill Stretch Headband
    Downhill Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Dalmatian Stretch Headband - The Sassy Olive Dalmatian Stretch Headband - The Sassy Olive
    Dalmatian Stretch Headband
    Dalmatian Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Cocker Spaniel Stretch Headband - The Sassy Olive Cocker Spaniel Stretch Headband - The Sassy Olive
    Cocker Spaniel Stretch Headband
    Cocker Spaniel Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Seaside Blooms Boho Buff - The Sassy Olive Seaside Blooms Boho Buff - The Sassy Olive
    Seaside Blooms Boho Buff
    Seaside Blooms Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Smiley Daisies Boho Buff - The Sassy Olive Smiley Daisies Boho Buff - The Sassy Olive
    Smiley Daisies Boho Buff
    Smiley Daisies Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Monarch Garden Boho Buff - The Sassy Olive Monarch Garden Boho Buff - The Sassy Olive
    Monarch Garden Boho Buff
    Monarch Garden Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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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
    Add to cart
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  • Stevie Floral Benzie Cap - The Sassy Olive Stevie Floral Benzie Cap - The Sassy Olive
    Stevie Floral Sassy Cap
    Stevie Floral Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Stargazing with Vincent Benzie Cap - The Sassy Olive Stargazing with Vincent Benzie Cap - The Sassy Olive
    Stargazing with Vincent Sassy Cap
    Stargazing with Vincent Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Flower Glade Benzie Cap - The Sassy Olive Flower Glade Benzie Cap - The Sassy Olive
    Flower Glade Sassy Cap
    Flower Glade Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Cats by CloudKBD Slouchy Beanie - The Sassy Olive Cats by CloudKBD Slouchy Beanie
    Cats by CloudKBD Slouchy Beanie
    Cats by CloudKBD Slouchy Beanie
    Regular price
    $25.00
    Regular price
    Sale price
    $25.00
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  • Lodge Life Slouchy Beanie - The Sassy Olive Lodge Life Slouchy Beanie - The Sassy Olive
    Lodge Life Slouchy Beanie
    Lodge Life Slouchy Beanie
    Regular price
    $25.00
    Regular price
    Sale price
    $25.00
    Add to cart
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  • Mini Pink Polka Dots Topknot Headband - The Sassy Olive Mini Pink Polka Dots Topknot Headband - The Sassy Olive
    Mini Pink Polka Dots Topknot Headband
    Mini Pink Polka Dots Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Country Club Stretch Headband - The Sassy Olive Country Club Stretch Headband - The Sassy Olive
    Country Club Stretch Headband
    Country Club Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Rainbow Cattle Ranch Stretch Headband - The Sassy Olive Rainbow Cattle Ranch Stretch Headband - The Sassy Olive
    Rainbow Cattle Ranch Stretch Headband
    Rainbow Cattle Ranch Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Skull Lights Wrap Headband - The Sassy Olive Skull Lights Wrap Headband - The Sassy Olive
    Skull Lights Wrap Headband
    Skull Lights Wrap Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Cute Spooky Cats Stretch Headband - The Sassy Olive Cute Spooky Cats Stretch Headband - The Sassy Olive
    Cute Spooky Cats Stretch Headband
    Cute Spooky Cats Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Smoke Paisley Top Knot Headband Smoke Paisley Top Knot Headband
    Smoke Paisley Top Knot Headband
    Smoke Paisley Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sahara Paisley Wrap Headband - The Sassy Olive Sahara Paisley Wrap Headband - The Sassy Olive
    Sahara Paisley Wrap Headband
    Sahara Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Sugar Cones Stretch Headband - The Sassy Olive Sugar Cones Stretch Headband - The Sassy Olive
    Sugar Cones Stretch Headband
    Sugar Cones Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Blush Pink Solid Wrap Headband - The Sassy Olive Blush Pink Solid Wrap Headband - The Sassy Olive
    Blush Pink Solid Wrap Headband
    Blush Pink Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Prickly Pear Cactus Stretch Headband - The Sassy Olive Prickly Pear Cactus Stretch Headband - The Sassy Olive
    Prickly Pear Cactus Stretch Headband
    Prickly Pear Cactus Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Dive Bar Stretch Headband - The Sassy Olive Dive Bar Stretch Headband - The Sassy Olive
    Dive Bar Stretch Headband
    Dive Bar Stretch Headband
    Regular price
    $15.00
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  • Mandala U of M Stretch Headband - The Sassy Olive Mandala U of M Stretch Headband - The Sassy Olive
    Mandala U of M Stretch Headband
    Mandala U of M Stretch Headband
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  • Pure Paws Wrap Headband - The Sassy Olive Pure Paws Wrap Headband - The Sassy Olive
    Pure Paws Wrap Headband
    Pure Paws Wrap Headband
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  • Ditzy Pink Floral Stretch Headband - The Sassy Olive Ditzy Pink Floral Stretch Headband - The Sassy Olive
    Ditzy Pink Floral Stretch Headband
    Ditzy Pink Floral Stretch Headband
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  • Saltwater Sketch Stretch Headband - The Sassy Olive Saltwater Sketch Stretch Headband - The Sassy Olive
    Saltwater Sketch Stretch Headband
    Saltwater Sketch Stretch Headband
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  • Palm Party Stretch Headband - The Sassy Olive Palm Party Stretch Headband - The Sassy Olive
    Palm Party Stretch Headband
    Palm Party Stretch Headband
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  • Queen C Stretch Headband - The Sassy Olive Queen C Stretch Headband - The Sassy Olive
    Queen C Stretch Headband
    Queen C Stretch Headband
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  • Y2K Confetti Polka Dot Stretch Headband - The Sassy Olive Y2K Confetti Polka Dot Stretch Headband - The Sassy Olive
    Y2K Confetti Polka Dot Stretch Headband
    Y2K Confetti Polka Dot Stretch Headband
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  • Navy Polka Dot Top Knot Headband Navy Polka Dot Top Knot Headband - The Sassy Olive
    Navy Polka Dot Top Knot Headband
    Navy Polka Dot Top Knot Headband
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  • Classic Black Polka Dot Stretch Headband - The Sassy Olive Classic Black Polka Dot Stretch Headband - The Sassy Olive
    Classic Black Polka Dot Stretch Headband
    Classic Black Polka Dot Stretch Headband
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  • Wine and Dine Scrunchie Pack - The Sassy Olive Wine and Dine Scrunchie Pack - The Sassy Olive
    Wine and Dine Scrunchie Pack
    Wine and Dine Scrunchie Pack
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    $18.00
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  • Whispering Vine Wrap Headband - The Sassy Olive Whispering Vine Wrap Headband - The Sassy Olive
    Whispering Vine Wrap Headband
    Whispering Vine Wrap Headband
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