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Collection: All Products

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

  • 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
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    $15.00
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  • Boho Punch Wrap Headband - The Sassy Olive Boho Punch Wrap Headband - The Sassy Olive
    Boho Punch Wrap Headband
    Boho Punch Wrap Headband
    Regular price
    $18.00
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    $18.00
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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
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    $15.00
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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
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    $15.00
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  • Toasty Stretch Headband - The Sassy Olive Toasty Stretch Headband - The Sassy Olive
    Toasty Stretch Headband
    Toasty Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Casting Spells Stretch Headband - The Sassy Olive Casting Spells Stretch Headband - The Sassy Olive
    Casting Spells Stretch Headband
    Casting Spells Stretch Headband
    Regular price
    $15.00
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    $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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  • Moon Hands Stretch Headband - The Sassy Olive Moon Hands Stretch Headband - The Sassy Olive
    Moon Hands Stretch Headband
    Moon Hands Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Salem Stretch Headband - The Sassy Olive Salem Stretch Headband - The Sassy Olive
    Salem Stretch Headband
    Salem Stretch Headband
    Regular price
    $15.00
    Regular price
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    $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
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    $15.00
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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
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    $15.00
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  • The Occult Wrap Headband - The Sassy Olive The Occult Wrap Headband - The Sassy Olive
    The Occult Wrap Headband
    The Occult Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Sage Camo Stretch Headband - The Sassy Olive Sage Camo Stretch Headband - The Sassy Olive
    Sage Camo Stretch Headband
    Sage Camo Stretch Headband
    Regular price
    $15.00
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    Sale price
    $15.00
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  • Mudcloth Arrow Stretch Headband - The Sassy Olive Mudcloth Arrow Stretch Headband - The Sassy Olive
    Mudcloth Arrow Stretch Headband
    Mudcloth Arrow Stretch Headband
    Regular price
    $15.00
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    $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
    Regular price
    $18.00
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    $18.00
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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
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    $18.00
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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
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    $15.00
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  • Bohoshade Sunflower Stretch Headband - The Sassy Olive Bohoshade Sunflower Stretch Headband - The Sassy Olive
    Bohoshade Sunflower Stretch Headband
    Bohoshade Sunflower Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • That 70& That 70&
    That 70's Kitchen Stretch Headband
    That 70's Kitchen Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Grey Petoskey Stretch Headband - The Sassy Olive Grey Petoskey Stretch Headband - The Sassy Olive
    Grey Petoskey Stretch Headband
    Grey Petoskey Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Australian Shepard Stretch Headband - The Sassy Olive Australian Shepard Stretch Headband - The Sassy Olive
    Australian Shepard Stretch Headband
    Australian Shepard Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Beagle Stretch Headband - The Sassy Olive Beagle Stretch Headband - The Sassy Olive
    Beagle Stretch Headband
    Beagle Stretch Headband
    Regular price
    $15.00
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    $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
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    Sale price
    $15.00
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  • Bulldog Stretch Headband - The Sassy Olive Bulldog Stretch Headband - The Sassy Olive
    Bulldog Stretch Headband
    Bulldog Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Catahoula Stretch Headband - The Sassy Olive Catahoula Stretch Headband - The Sassy Olive
    Catahoula Stretch Headband
    Catahoula Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Chihuahua Stretch Headband - The Sassy Olive Chihuahua Stretch Headband - The Sassy Olive
    Chihuahua Stretch Headband
    Chihuahua Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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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  • Corgi Stretch Headband - The Sassy Olive Corgi Stretch Headband - The Sassy Olive
    Corgi Stretch Headband
    Corgi Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
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    $15.00
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  • Dachshund Stretch Headband - The Sassy Olive Dachshund Stretch Headband - The Sassy Olive
    Dachshund Stretch Headband
    Dachshund Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Doberman Stretch Headband - The Sassy Olive Doberman Stretch Headband - The Sassy Olive
    Doberman Stretch Headband
    Doberman Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
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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
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  • Great Pyrenees Stretch Headband - The Sassy Olive Great Pyrenees Stretch Headband - The Sassy Olive
    Great Pyrenees Stretch Headband
    Great Pyrenees Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Husky Stretch Headband - The Sassy Olive Husky Stretch Headband - The Sassy Olive
    Husky Stretch Headband
    Husky Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Jack Russel Stretch Headband - The Sassy Olive Jack Russel Stretch Headband - The Sassy Olive
    Jack Russel Stretch Headband
    Jack Russel Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Labradoodle Stretch Headband - The Sassy Olive Labradoodle Stretch Headband - The Sassy Olive
    Labradoodle Stretch Headband
    Labradoodle Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pitbull Stretch Headband - The Sassy Olive Pitbull Stretch Headband - The Sassy Olive
    Pitbull Stretch Headband
    Pitbull Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Rottweiler Stretch Headband - The Sassy Olive Rottweiler Stretch Headband - The Sassy Olive
    Rottweiler Stretch Headband
    Rottweiler Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Schnauzer Stretch Headband - The Sassy Olive Schnauzer Stretch Headband - The Sassy Olive
    Schnauzer Stretch Headband
    Schnauzer Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Scottish Terrier Stretch Headband - The Sassy Olive Scottish Terrier Stretch Headband - The Sassy Olive
    Scottish Terrier Stretch Headband
    Scottish Terrier Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Shitzu Stretch Headband - The Sassy Olive Shitzu Stretch Headband - The Sassy Olive
    Shitzu Stretch Headband
    Shitzu Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • AYSO Stretch Headband - The Sassy Olive AYSO Stretch Headband - The Sassy Olive
    AYSO Stretch Headband
    AYSO Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Bittersweet Stretch Headband - The Sassy Olive Bittersweet Stretch Headband - The Sassy Olive
    Bittersweet Stretch Headband
    Bittersweet Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • MTB Stretch Headband - The Sassy Olive MTB Stretch Headband - The Sassy Olive
    MTB Stretch Headband
    MTB Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Cheshire Hills Stretch Headband - The Sassy Olive Cheshire Hills Stretch Headband - The Sassy Olive
    Cheshire Hills Stretch Headband
    Cheshire Hills Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Detroit Lions Stretch Headband - The Sassy Olive Detroit Lions Stretch Headband - The Sassy Olive
    Detroit Lions Stretch Headband
    Detroit Lions Stretch Headband
    Regular price
    $15.00
    Regular price
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    $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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  • Detroit Tigers Stretch Headband - The Sassy Olive Detroit Tigers Stretch Headband - The Sassy Olive
    Detroit Tigers Stretch Headband
    Detroit Tigers Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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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
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    $15.00
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  • Fastpitch Stretch Headband - The Sassy Olive Fastpitch Stretch Headband - The Sassy Olive
    Fastpitch Stretch Headband
    Fastpitch Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • First Base Stretch Headband - The Sassy Olive First Base Stretch Headband - The Sassy Olive
    First Base Stretch Headband
    First Base Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Game, Set, Match Stretch Headband - The Sassy Olive Game, Set, Match Stretch Headband - The Sassy Olive
    Game, Set, Match Stretch Headband
    Game, Set, Match Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Harlem Globetrotters Stretch Headband - The Sassy Olive Harlem Globetrotters Stretch Headband - The Sassy Olive
    Harlem Globetrotters Stretch Headband
    Harlem Globetrotters Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Heavyweight Stretch Headband - The Sassy Olive Heavyweight Stretch Headband - The Sassy Olive
    Heavyweight Stretch Headband
    Heavyweight Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Ice, Ice, Skate Stretch Headband - The Sassy Olive Ice, Ice, Skate Stretch Headband - The Sassy Olive
    Ice, Ice, Skate Stretch Headband
    Ice, Ice, Skate Stretch Headband
    Regular price
    $15.00
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    $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
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    $15.00
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  • Pickle Pals Stretch Headband - The Sassy Olive Pickle Pals Stretch Headband - The Sassy Olive
    Pickle Pals Stretch Headband
    Pickle Pals Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Wet n& Wet n&
    Wet n' Wild Stretch Headband
    Wet n' Wild Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Mystery Headband Bag – 5 for $25 - The Sassy Olive Mystery Headband Bag – 5 for $25 - The Sassy Olive
    Mystery Bag 5 Headband Grab Bag
    Mystery Bag 5 Headband Grab Bag
    Regular price
    $25.00
    Regular price
    Sale price
    $25.00
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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
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    $15.00
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  • Bohemian Terrain Stretch Headband - The Sassy Olive Bohemian Terrain Stretch Headband - The Sassy Olive
    Bohemian Terrain Stretch Headband
    Bohemian Terrain Stretch Headband
    Regular price
    $15.00
    Regular price
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    $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
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    $15.00
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  • Dusk in Autumn Stretch Headband - The Sassy Olive Dusk in Autumn Stretch Headband - The Sassy Olive
    Dusk in Autumn Stretch Headband
    Dusk in Autumn Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Dusk in Autumn Wrap Headband - The Sassy Olive Dusk in Autumn Wrap Headband - The Sassy Olive
    Dusk in Autumn Wrap Headband
    Dusk in Autumn Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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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
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    $15.00
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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
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    $18.00
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  • Classy Bitch Stretch Headband - The Sassy Olive Classy Bitch Stretch Headband - The Sassy Olive
    Classy Bitch Stretch Headband
    Classy Bitch Stretch Headband
    Regular price
    $15.00
    Regular price
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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
    Regular price
    $15.00
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    $15.00
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  • Fuck Directly Off Stretch Headband - The Sassy Olive Fuck Directly Off Stretch Headband - The Sassy Olive
    Fuck Directly Off Stretch Headband
    Fuck Directly Off Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Sage that Shit Stretch Headband - The Sassy Olive Sage that Shit Stretch Headband - The Sassy Olive
    Sage that Shit Stretch Headband
    Sage that Shit Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Popcorn! Stretch Headband - The Sassy Olive Popcorn! Stretch Headband - The Sassy Olive
    Popcorn! Stretch Headband
    Popcorn! Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $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
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  • Balance Paisley Wrap Headband - The Sassy Olive Balance Paisley Wrap Headband - The Sassy Olive
    Balance Paisley Wrap Headband
    Balance Paisley Wrap Headband
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  • Funky Fresh Paisley Stretch Headband - The Sassy Olive Funky Fresh Paisley Stretch Headband - The Sassy Olive
    Funky Fresh Paisley Stretch Headband
    Funky Fresh Paisley Stretch Headband
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  • Funky Fresh Paisley Wrap Headband - The Sassy Olive Funky Fresh Paisley Wrap Headband - The Sassy Olive
    Funky Fresh Paisley Wrap Headband
    Funky Fresh Paisley Wrap Headband
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  • Merzouga Paisley Stretch Headband - The Sassy Olive Merzouga Paisley Stretch Headband - The Sassy Olive
    Merzouga Paisley Stretch Headband
    Merzouga Paisley Stretch Headband
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  • Merzouga Paisley Wrap Headband - The Sassy Olive Merzouga Paisley Wrap Headband - The Sassy Olive
    Merzouga Paisley Wrap Headband
    Merzouga Paisley Wrap Headband
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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
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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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