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The Sassy OliveThe Sassy Olive
  • Shop
    Featured Collections
    • Newest Arrivals
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    • Book Club
    • 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
    • Floral
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    • Paisley
    • Solid Colors
    • Sports
    • Tie Dye
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    Shop by Vibe
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    • 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
  • Connect
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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

  • Cranberry Christmas Blooms Stretch Headband - The Sassy Olive Cranberry Christmas Blooms Stretch Headband - The Sassy Olive
    Cranberry Christmas Blooms Stretch Headband
    Cranberry Christmas Blooms Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Color Me Frosty Wrap Headband - The Sassy Olive Color Me Frosty Wrap Headband - The Sassy Olive
    Color Me Frosty Wrap Headband
    Color Me Frosty Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Christmas Cookies Stretch Headband - The Sassy Olive Christmas Cookies Stretch Headband - The Sassy Olive
    Christmas Cookies Stretch Headband
    Christmas Cookies Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Candy Cane Lane Wrap Headband - The Sassy Olive Candy Cane Lane Wrap Headband - The Sassy Olive
    Candy Cane Lane Wrap Headband
    Candy Cane Lane Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Cabin Cutie Stretch Headband - The Sassy Olive Cabin Cutie Stretch Headband - The Sassy Olive
    Cabin Cutie Stretch Headband
    Cabin Cutie Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • BooJee Christmas Stretch Headband - The Sassy Olive BooJee Christmas Stretch Headband - The Sassy Olive
    BooJee Christmas Stretch Headband
    BooJee Christmas Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Atomic Santa Stretch Headband - The Sassy Olive Atomic Santa Stretch Headband - The Sassy Olive
    Atomic Santa Stretch Headband
    Atomic Santa Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Golden Christmas Tree Stretch Headband - The Sassy Olive Golden Christmas Tree Stretch Headband - The Sassy Olive
    Golden Christmas Tree Stretch Headband
    Golden Christmas Tree Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
    Add to cart
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  • Wildfire Paisley Top Knot Headband - The Sassy Olive Wildfire Paisley Top Knot Headband - The Sassy Olive
    Wildfire Paisley Top Knot Headband
    Wildfire Paisley Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Porcelain Paisley Top Knot Headband - The Sassy Olive Porcelain Paisley Top Knot Headband - The Sassy Olive
    Porcelain Paisley Top Knot Headband
    Porcelain Paisley Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Inkwell Paisley Stretch Headband - The Sassy Olive Inkwell Paisley Stretch Headband - The Sassy Olive
    Inkwell Paisley Stretch Headband
    Inkwell Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Henna Paisley Top Knot Headband - The Sassy Olive Henna Paisley Top Knot Headband - The Sassy Olive
    Henna Paisley Top Knot Headband
    Henna Paisley Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Blueberry Season Headband Bundle - The Sassy Olive Blueberry Lemon Squeeze Stretch Headband - The Sassy Olive
    Blueberry Season Headband Bundle
    Blueberry Season Headband Bundle
    Regular price
    $75.00
    Regular price
    Sale price
    $75.00
    Add to cart
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  • Silver Solid Top Knot Headband - The Sassy Olive Silver Solid Top Knot Headband - The Sassy Olive
    Silver Solid Top Knot Headband
    Silver Solid Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Blush Pink Solid Top Knot Headband - The Sassy Olive Blush Pink Solid Top Knot Headband - The Sassy Olive
    Blush Pink Solid Top Knot Headband
    Blush Pink Solid Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Tan Solid Top Knot Headband - The Sassy Olive Tan Solid Top Knot Headband - The Sassy Olive
    Tan Solid Top Knot Headband
    Tan Solid Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Hawaiian Blue Solid Top Knot Headband - The Sassy Olive Hawaiian Blue Solid Top Knot Headband - The Sassy Olive
    Hawaiian Blue Solid Top Knot Headband
    Hawaiian Blue Solid Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Horses F1 Casino Random Ass Sass Stretch Headband - The Sassy Olive Horses F1 Casino Random Ass Sass Stretch Headband - The Sassy Olive
    Horses F1 Casino Random Ass Sass Stretch Headband
    Horses F1 Casino Random Ass Sass Stretch Headband
    Regular price
    $10.00
    Regular price
    Sale price
    $10.00
    Add to cart
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  • Ballerina Stretch Headband - The Sassy Olive Ballerina Stretch Headband - The Sassy Olive
    Ballerina Stretch Headband
    Ballerina Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • MSU Tie Dye Stretch Headband - The Sassy Olive MSU Tie Dye Stretch Headband - The Sassy Olive
    MSU Tie Dye Stretch Headband
    MSU Tie Dye Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Green Mandala MSU Stretch Headband - The Sassy Olive Green Mandala MSU Stretch Headband - The Sassy Olive
    Green Mandala MSU Stretch Headband
    Green Mandala MSU Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Wasabi Weave Wrap Headband - The Sassy Olive Wasabi Weave Wrap Headband - The Sassy Olive
    Wasabi Weave Wrap Headband
    Wasabi Weave Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Season’s Diamond Stretch Headband - The Sassy Olive Season’s Diamond Stretch Headband - The Sassy Olive
    Season’s Diamond Stretch Headband
    Season’s Diamond Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Masquerade Stretch Headband - The Sassy Olive Masquerade Stretch Headband - The Sassy Olive
    Masquerade Stretch Headband
    Masquerade Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Getaway Stretch Headband - The Sassy Olive Getaway Stretch Headband - The Sassy Olive
    Getaway Stretch Headband
    Getaway Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Y2K Blue & Brown Polka Dot Top Knot Headband Y2K Blue & Brown Polka Dot Top Knot Headband
    Y2K Blue & Brown Polka Dot Top Knot Headband
    Y2K Blue & Brown Polka Dot Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Victoria’s Pink Polka Dot Top Knot Headband Victoria’s Pink Polka Dot Top Knot Headband
    Victoria’s Pink Polka Dot Top Knot Headband
    Victoria’s Pink Polka Dot Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Activist Headband Bundle – Set of 5 Stretch Headbands - The Sassy Olive
    Activist Headband Bundle – Set of 5 Stretch Headbands
    Activist Headband Bundle – Set of 5 Stretch Headbands
    Regular price
    $70.00
    Regular price
    Sale price
    $70.00
    Add to cart
    Quick view
  • Hiking & Outdoors Headband Bundle (5 - Pack) - The Sassy Olive
    Hiking & Outdoors Headband Bundle (5-Pack)
    Hiking & Outdoors Headband Bundle (5-Pack)
    Regular price
    $65.00
    Regular price
    $75.00
    Sale price
    $65.00
    Similar products
    Sold out
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  • Nursing Workday Headband Bundle (5 - Pack) - The Sassy Olive
    Nursing Workday Headband Bundle (5-Pack)
    Nursing Workday Headband Bundle (5-Pack)
    Regular price
    $69.00
    Regular price
    $75.00
    Sale price
    $69.00
    Add to cart
    –$6.00
    Quick view
  • Everyday Sassy Essentials Bundle (6-Piece Set) - The Sassy Olive Wildfire Paisley Stretch Headband - The Sassy Olive
    Everyday Sassy Essentials Bundle (6-Piece Set)
    Everyday Sassy Essentials Bundle (6-Piece Set)
    Regular price
    $54.00
    Regular price
    $63.00
    Sale price
    $54.00
    Add to cart
    –$9.00
    Quick view
  • FRIENDS Headband Bundle (5 - Pack) - The Sassy Olive
    FRIENDS Headband Bundle (5-Pack)
    FRIENDS Headband Bundle (5-Pack)
    Regular price
    $50.00
    Regular price
    $60.00
    Sale price
    $50.00
    Add to cart
    –$10.00
    Quick view
  • Cat Mom Headband Bundle (5 - Pack) - The Sassy Olive
    Cat Mom Headband Bundle (5-Pack)
    Cat Mom Headband Bundle (5-Pack)
    Regular price
    $50.00
    Regular price
    $60.00
    Sale price
    $50.00
    Add to cart
    –$10.00
    Quick view
  • Fishing Headband Bundle (3 - Pack) - The Sassy Olive
    Fishing Headband Bundle (3-Pack)
    Fishing Headband Bundle (3-Pack)
    Regular price
    $30.00
    Regular price
    $36.00
    Sale price
    $30.00
    Add to cart
    –$6.00
    Quick view
  • Jeep Headband Bundle (3 - Pack) - The Sassy Olive
    Jeep Headband Bundle (3-Pack)
    Jeep Headband Bundle (3-Pack)
    Regular price
    $30.00
    Regular price
    $36.00
    Sale price
    $30.00
    Similar products
    Sold out
    Quick view
  • Michigan Wildflowers Wrap Headband - The Sassy Olive Michigan Wildflowers Wrap Headband - The Sassy Olive
    Michigan Wildflowers Wrap Headband
    Michigan Wildflowers Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Cherry Picnic Wrap Headband - The Sassy Olive Cherry Picnic Wrap Headband - The Sassy Olive
    Cherry Picnic Wrap Headband
    Cherry Picnic Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Spirits of Spring Wrap Headband - The Sassy Olive Spirits of Spring Wrap Headband - The Sassy Olive
    Spirits of Spring Wrap Headband
    Spirits of Spring Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Love Buds Topknot Headband - The Sassy Olive Love Buds Topknot Headband - The Sassy Olive
    Love Buds Topknot Headband
    Love Buds Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Blueberry Donuts Top Knot Headband Blueberry Donuts Top Knot Headband - The Sassy Olive
    Blueberry Donuts Top Knot Headband
    Blueberry Donuts Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Sassy Sardines Topknot Headband - The Sassy Olive Sassy Sardines Topknot Headband - The Sassy Olive
    Sassy Sardines Topknot Headband
    Sassy Sardines Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Cherry Martini Topknot Headband - The Sassy Olive Cherry Martini Topknot Headband - The Sassy Olive
    Cherry Martini Topknot Headband
    Cherry Martini Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Wildflower Wander Topknot Headband - The Sassy Olive Wildflower Wander Topknot Headband - The Sassy Olive
    Wildflower Wander Topknot Headband
    Wildflower Wander Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Petal Patch Topknot Headband - The Sassy Olive Petal Patch Topknot Headband - The Sassy Olive
    Petal Patch Topknot Headband
    Petal Patch Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Blossom Breeze Topknot Headband - The Sassy Olive Blossom Breeze Topknot Headband - The Sassy Olive
    Blossom Breeze Topknot Headband
    Blossom Breeze Topknot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Yellow Bell Floral Top Knot Headband - The Sassy Olive Yellow Bell Floral Top Knot Headband - The Sassy Olive
    Yellow Bell Floral Top Knot Headband
    Yellow Bell Floral Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Lucky Horseshoes Top Knot Headband - The Sassy Olive Lucky Horseshoes Top Knot Headband - The Sassy Olive
    Lucky Horseshoes Top Knot Headband
    Lucky Horseshoes Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Orange Couch Top Knot Headband - The Sassy Olive Orange Couch Top Knot Headband - The Sassy Olive
    Orange Couch Top Knot Headband
    Orange Couch Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Reputation Top Knot Headband - The Sassy Olive Reputation Top Knot Headband - The Sassy Olive
    Reputation Top Knot Headband
    Reputation Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Red Cassette Top Knot Headband - The Sassy Olive Red Cassette Top Knot Headband - The Sassy Olive
    Red Cassette Top Knot Headband
    Red Cassette Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Autumn Curtain Stretch Headband - The Sassy Olive Autumn Curtain Stretch Headband - The Sassy Olive
    Autumn Curtain Stretch Headband
    Autumn Curtain Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Sassy - Cuterie Stretch Headband - The Sassy Olive Sassy - Cuterie Stretch Headband - The Sassy Olive
    Sassy-Cuterie Stretch Headband
    Sassy-Cuterie Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
    Add to cart
    Quick view
  • Rubber Plant Top Knot Headband - The Sassy Olive Rubber Plant Top Knot Headband - The Sassy Olive
    Rubber Plant Top Knot Headband
    Rubber Plant Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Plaque Attack Stretch Headband - The Sassy Olive Plaque Attack Stretch Headband - The Sassy Olive
    Plaque Attack Stretch Headband
    Plaque Attack Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Contact Lens Stretch Headband - The Sassy Olive Contact Lens Stretch Headband - The Sassy Olive
    Contact Lens Stretch Headband
    Contact Lens Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Brace Face Stretch Headband - The Sassy Olive Brace Face Stretch Headband - The Sassy Olive
    Brace Face Stretch Headband
    Brace Face Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Game On Stretch Headband - The Sassy Olive Game On Stretch Headband - The Sassy Olive
    Game On Stretch Headband
    Game On Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
    Add to cart
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  • Blueberry Donuts Stretch Headband - The Sassy Olive Blueberry Donuts Stretch Headband - The Sassy Olive
    Blueberry Donuts Stretch Headband
    Blueberry Donuts Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Fuji Apple Stretch Headband - The Sassy Olive Fuji Apple Stretch Headband - The Sassy Olive
    Fuji Apple Stretch Headband
    Fuji Apple Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Crystal Chiweenie Water Bottle Random Ass Stretch - The Sassy Olive Crystal Chiweenie Water Bottle Random Ass Stretch - The Sassy Olive
    Crystal Chiweenie Water Bottle Random Ass Stretch Headband
    Crystal Chiweenie Water Bottle Random Ass Stretch Headband
    Regular price
    $10.00
    Regular price
    Sale price
    $10.00
    Add to cart
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  • KVCC Stretch Headband - The Sassy Olive KVCC Stretch Headband - The Sassy Olive
    KVCC Stretch Headband
    KVCC Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Kalamazoo College Stretch Headband - The Sassy Olive Kalamazoo College Stretch Headband - The Sassy Olive
    Kalamazoo College Stretch Headband
    Kalamazoo College Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Ask Me Pronouns Stretch Headband - The Sassy Olive Ask Me Pronouns Stretch Headband - The Sassy Olive
    Ask Me Pronouns Stretch Headband
    Ask Me Pronouns Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • He/Him Pronouns Stretch Headband - The Sassy Olive He/Him Pronouns Stretch Headband - The Sassy Olive
    He/Him Pronouns Stretch Headband
    He/Him Pronouns Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Corn Penguid Sasshole Random Ass Stretch - The Sassy Olive Corn Penguid Sasshole Random Ass Stretch - The Sassy Olive
    Corn Penguin Sasshole Random Ass Stretch Headband
    Corn Penguin Sasshole Random Ass Stretch Headband
    Regular price
    $10.00
    Regular price
    Sale price
    $10.00
    Add to cart
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  • International Climbers Stretch Headband - The Sassy Olive International Climbers Stretch Headband - The Sassy Olive
    International Climbers Stretch Headband
    International Climbers Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Autumn Curtain Boho Buff - The Sassy Olive Autumn Curtain Boho Buff - The Sassy Olive
    Autumn Curtain Boho Buff
    Autumn Curtain Boho Buff
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  • Happy Kelly Solid Green Boho Buff - The Sassy Olive Happy Kelly Solid Green Boho Buff - The Sassy Olive
    Happy Kelly Green Solid Boho Buff
    Happy Kelly Green Solid Boho Buff
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  • Gingerbread Solid Brown Boho Buff - The Sassy Olive Gingerbread Solid Brown Boho Buff - The Sassy Olive
    Caramel Brown Solid Boho Buff
    Caramel Brown Solid Boho Buff
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    $18.00
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  • Sunlit Meadow Boho Buff - The Sassy Olive Sunlit Meadow Boho Buff - The Sassy Olive
    Sunlit Meadow Boho Buff
    Sunlit Meadow Boho Buff
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    $18.00
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