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The Sassy OliveThe Sassy Olive
  • Shop
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    Shop by Type
    • Stretch Headbands
    • Top Knot Headbands
    • Wrap Headbands
    • Twist Headbands
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    • Slouchy Beanies
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    • All Styles
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    • Athletic
    • Minimal
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    • 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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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

  • Wasiliewski Paisley Stretch Headband - The Sassy Olive Wasiliewski Paisley Stretch Headband - The Sassy Olive
    Wasiliewski Paisley Stretch Headband
    Wasiliewski Paisley Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Ultrasound Tech Stretch Headband - The Sassy Olive Ultrasound Tech Stretch Headband - The Sassy Olive
    Ultrasound Tech Stretch Headband
    Ultrasound Tech Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Wardrobe Stretch Headband - The Sassy Olive Wardrobe Stretch Headband - The Sassy Olive
    Wardrobe Stretch Headband
    Wardrobe Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • PacMan Stretch Headband - The Sassy Olive PacMan Stretch Headband - The Sassy Olive
    PacMan Stretch Headband
    PacMan Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Balance Paisley Stretch Headband - The Sassy Olive Balance Paisley Stretch Headband - The Sassy Olive
    Balance Paisley Stretch Headband
    Balance Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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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  • Colleen Floral Stretch Headband - The Sassy Olive Colleen Floral Stretch Headband - The Sassy Olive
    Colleen Floral Stretch Headband
    Colleen Floral Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sssnake Stretch Headband - The Sassy Olive Sssnake Stretch Headband - The Sassy Olive
    Sssnake Stretch Headband
    Sssnake Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Piles of Smiles Stretch Headband - The Sassy Olive Piles of Smiles Stretch Headband - The Sassy Olive
    Piles of Smiles Stretch Headband
    Piles of Smiles Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sunny Jeeps Stretch Headband - The Sassy Olive Sunny Jeeps Stretch Headband - The Sassy Olive
    Sunny Jeeps Stretch Headband
    Sunny Jeeps Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Black Cats Stretch Headband - The Sassy Olive Black Cats Stretch Headband - The Sassy Olive
    Black Cats Stretch Headband
    Black Cats Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Moroccan Summer Stretch Headband - The Sassy Olive Moroccan Summer Stretch Headband - The Sassy Olive
    Moroccan Summer Stretch Headband
    Moroccan Summer Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Kalamazoo River Stretch Headband - The Sassy Olive Kalamazoo River Stretch Headband - The Sassy Olive
    Kalamazoo River Stretch Headband
    Kalamazoo River Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Couch Green Solid Stretch Headband - The Sassy Olive Couch Green Solid Stretch Headband - The Sassy Olive
    Couch Green Solid Stretch Headband
    Couch Green Solid Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Yellow Bell Floral Stretch Headband - The Sassy Olive Yellow Bell Floral Stretch Headband - The Sassy Olive
    Yellow Bell Floral Stretch Headband
    Yellow Bell Floral Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Beetles Stretch Headband - The Sassy Olive Beetles Stretch Headband - The Sassy Olive
    Beetles Stretch Headband
    Beetles Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Turtle Club Stretch Headband - The Sassy Olive Turtle Club Stretch Headband - The Sassy Olive
    Turtle Club Stretch Headband
    Turtle Club Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Toe Beans Stretch Headband - The Sassy Olive Toe Beans Stretch Headband - The Sassy Olive
    Toe Beans Stretch Headband
    Toe Beans Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Lions Football Fan Stretch Headband - The Sassy Olive Lions Football Fan Stretch Headband - The Sassy Olive
    Lions Football Fan Stretch Headband
    Lions Football Fan Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • High Freq Vibes Stretch Headband - The Sassy Olive High Freq Vibes Stretch Headband - The Sassy Olive
    High Freq Vibes Stretch Headband
    High Freq Vibes Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Detroit Red Wings Stretch Headband - The Sassy Olive Detroit Red Wings Stretch Headband - The Sassy Olive
    Detroit Red Wings Stretch Headband
    Detroit Red Wings Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Medici Floral Wrap Headband - The Sassy Olive Medici Floral Wrap Headband - The Sassy Olive
    Medici Floral Wrap Headband
    Medici Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Scan Till It Hurtz Stretch Headband - The Sassy Olive Scan Till It Hurtz Stretch Headband - The Sassy Olive
    Scan Till It Hurtz Stretch Headband
    Scan Till It Hurtz Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Dark Splatter Stretch Headband - The Sassy Olive Dark Splatter Stretch Headband - The Sassy Olive
    Dark Splatter Stretch Headband
    Dark Splatter Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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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  • A Heart is a Heart is a Heart Stretch Headband - The Sassy Olive A Heart is a Heart is a Heart Stretch Headband - The Sassy Olive
    A Heart is a Heart is a Heart Stretch Headband
    A Heart is a Heart is a Heart Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Out of this World Stretch Headband - The Sassy Olive Out of this World Stretch Headband - The Sassy Olive
    Out of this World Stretch Headband
    Out of this World Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Moonlight Morels Stretch Headband - The Sassy Olive Moonlight Morels Stretch Headband - The Sassy Olive
    Moonlight Morels Stretch Headband
    Moonlight Morels Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Bulldogger Stretch Headband - The Sassy Olive Bulldogger Stretch Headband - The Sassy Olive
    Bulldogger Stretch Headband
    Bulldogger Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Adventure Stretch Headband - The Sassy Olive Adventure Stretch Headband - The Sassy Olive
    Adventure Stretch Headband
    Adventure Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Marshmallow White Solid Stretch Headband - The Sassy Olive Marshmallow White Solid Stretch Headband - The Sassy Olive
    Marshmallow White Solid Stretch Headband
    Marshmallow White Solid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Madie& Madie&
    Madie's Mushroom Stretch Headband
    Madie's Mushroom Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Patricia Paisley Stretch Headband - The Sassy Olive Patricia Paisley Stretch Headband - The Sassy Olive
    Patricia Paisley Stretch Headband
    Patricia Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • What the Cluck Stretch Headband - The Sassy Olive What the Cluck Stretch Headband - The Sassy Olive
    What the Cluck Stretch Headband
    What the Cluck Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Spilled Vibe Stretch Headband - The Sassy Olive Spilled Vibe Stretch Headband - The Sassy Olive
    Spilled Vibe Stretch Headband
    Spilled Vibe Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Cat Mom Stretch Headband - The Sassy Olive Cat Mom Stretch Headband - The Sassy Olive
    Cat Mom Stretch Headband
    Cat Mom Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pretty Purple Nurse Stretch Headband - The Sassy Olive Pretty Purple Nurse Stretch Headband - The Sassy Olive
    Pretty Purple Nurse Stretch Headband
    Pretty Purple Nurse Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Garden Scribe Stretch Headband - The Sassy Olive Garden Scribe Stretch Headband - The Sassy Olive
    Garden Scribe Stretch Headband
    Garden Scribe Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • National Park Pass Stretch Headband - The Sassy Olive National Park Pass Stretch Headband - The Sassy Olive
    National Park Pass Stretch Headband
    National Park Pass Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Similar products
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  • Golden Retriever Stretch Headband - The Sassy Olive Golden Retriever Stretch Headband - The Sassy Olive
    Golden Retriever Stretch Headband
    Golden Retriever Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Berry Red Solid Stretch Headband - The Sassy Olive Berry Red Solid Stretch Headband - The Sassy Olive
    Berry Red Solid Stretch Headband
    Berry Red Solid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Townsend Tie Dye Stretch Headband - The Sassy Olive Townsend Tie Dye Stretch Headband - The Sassy Olive
    Townsend Tie Dye Stretch Headband
    Townsend Tie Dye Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Lungs Of Love Stretch Headband - The Sassy Olive Lungs Of Love Stretch Headband - The Sassy Olive
    Lungs Of Love Stretch Headband
    Lungs Of Love 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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  • Ew, David Stretch Headband - The Sassy Olive Ew, David Stretch Headband - The Sassy Olive
    Ew, David Stretch Headband
    Ew, David Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Casting Spells Wrap Headband - The Sassy Olive Casting Spells Wrap Headband - The Sassy Olive
    Casting Spells Wrap Headband
    Casting Spells Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • German Shepard Green Stretch Headband - The Sassy Olive German Shepard Green Stretch Headband - The Sassy Olive
    German Shepard Green Stretch Headband
    German Shepard Green Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Benzie& Benzie&
    Benzie's Friends Stretch Headband
    Benzie's Friends Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • L - O - V - EKG Stretch Headband - The Sassy Olive L - O - V - EKG Stretch Headband - The Sassy Olive
    L-O-V-EKG Stretch Headband
    L-O-V-EKG Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Puppy Garden Stretch Headband - The Sassy Olive Puppy Garden Stretch Headband - The Sassy Olive
    Puppy Garden Stretch Headband
    Puppy Garden Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Beach Glass Stretch Headband - The Sassy Olive Beach Glass Stretch Headband - The Sassy Olive
    Beach Glass Stretch Headband
    Beach Glass Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Blue Whimsy Cat Stretch Headband - The Sassy Olive Blue Whimsy Cat Stretch Headband - The Sassy Olive
    Blue Whimsy Cat Stretch Headband
    Blue Whimsy Cat Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mermaid Tails Stretch Headband - The Sassy Olive Mermaid Tails Stretch Headband - The Sassy Olive
    Mermaid Tails Stretch Headband
    Mermaid Tails Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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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
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    $15.00
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  • Bird Nerd Stretch Headband - The Sassy Olive Bird Nerd Stretch Headband - The Sassy Olive
    Bird Nerd Stretch Headband
    Bird Nerd Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Similar products
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  • Monstera Stretch Headband - The Sassy Olive Monstera Stretch Headband - The Sassy Olive
    Monstera Stretch Headband
    Monstera Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Abalone Stretch Headband - The Sassy Olive Abalone Stretch Headband - The Sassy Olive
    Abalone Stretch Headband
    Abalone Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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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
    Regular price
    Sale price
    $15.00
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  • Goodnight Garden Wrap Headband - The Sassy Olive Goodnight Garden Wrap Headband - The Sassy Olive
    Goodnight Garden Wrap Headband
    Goodnight Garden Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Michigan Beach Glass Stretch Headband - The Sassy Olive Michigan Beach Glass Stretch Headband - The Sassy Olive
    Michigan Beach Glass Stretch Headband
    Michigan Beach Glass Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Gel Yeah Stretch Headband - The Sassy Olive Gel Yeah Stretch Headband - The Sassy Olive
    Gel Yeah Stretch Headband
    Gel Yeah Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Ansel Stretch Headband - The Sassy Olive Ansel Stretch Headband - The Sassy Olive
    Ansel Stretch Headband
    Ansel Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Lillian Harper Tie Dye Stretch Headband - The Sassy Olive Lillian Harper Tie Dye Stretch Headband - The Sassy Olive
    Lillian Harper Tie Dye Stretch Headband
    Lillian Harper Tie Dye Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Heeler Stretch Headband - The Sassy Olive Heeler Stretch Headband - The Sassy Olive
    Heeler Stretch Headband
    Heeler Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Daphne Floral Wrap Headband - The Sassy Olive Daphne Floral Wrap Headband - The Sassy Olive
    Daphne Floral Wrap Headband
    Daphne Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Midnight Mandala Paisley Stretch Headband - The Sassy Olive Midnight Mandala Paisley Stretch Headband - The Sassy Olive
    Midnight Mandala Paisley Stretch Headband
    Midnight Mandala Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
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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
    Add to cart
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  • Good Morning Stretch Headband - The Sassy Olive Good Morning Stretch Headband - The Sassy Olive
    Good Morning Stretch Headband
    Good Morning Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mudcloth Arrow Wrap Headband - The Sassy Olive Mudcloth Arrow Wrap Headband - The Sassy Olive
    Mudcloth Arrow Wrap Headband
    Mudcloth Arrow Wrap Headband
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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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  • Fresh Lee Stretch Headband Fresh Lee Stretch Headband - The Sassy Olive
    Fresh Lee Stretch Headband
    Fresh Lee Stretch Headband
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    $15.00
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    $15.00
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  • Pateast Paisley Stretch Headband - The Sassy Olive Pateast Paisley Stretch Headband - The Sassy Olive
    Pateast Paisley Stretch Headband
    Pateast Paisley Stretch Headband
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  • Tim& Tim&
    Tim's Ladies Stretch Headband
    Tim's Ladies Stretch Headband
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  • Alaric Floral Wrap Headband - The Sassy Olive Alaric Floral Wrap Headband - The Sassy Olive
    Alaric Floral Wrap Headband
    Alaric Floral Wrap Headband
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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
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    $15.00
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    $15.00
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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
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    $15.00
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  • Succulent Crystals Stretch Headband - The Sassy Olive Succulent Crystals Stretch Headband
    Succulent Crystals Stretch Headband
    Succulent Crystals Stretch Headband
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    $15.00
    Regular price
    $12.00
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    $15.00
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  • Woodland Camo Stretch Headband - The Sassy Olive Woodland Camo Stretch Headband - The Sassy Olive
    Woodland Camo Stretch Headband
    Woodland Camo Stretch Headband
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    $15.00
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    $15.00
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  • F - Word Stretch Headband - The Sassy Olive F - Word Stretch Headband - The Sassy Olive
    F-Word Stretch Headband
    F-Word Stretch Headband
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