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    Special Offers
    • The Sassy "Style Me" Box
    • Grab Bags
    • Bundle Deals
    • Gift Card
    • Sale
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    • Personalize & Pet Face
    • Custom Headbands
    • Special Request Product
    • Custom Fabric Printing
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    • Stretch
    • Wrap
    • Top Knot
    • Twist
    • Short Hair
    • Headbands with Bangs
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Collection: All Headbands

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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1486 products
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1486 products

  • 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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  • Backbone Baddie Stretch Headband - The Sassy Olive Backbone Baddie Stretch Headband - The Sassy Olive
    Backbone Baddie Stretch Headband
    Backbone Baddie Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Blazey Susan Stretch Headband - The Sassy Olive Blazey Susan Stretch Headband - The Sassy Olive
    Blazey Susan Stretch Headband
    Blazey Susan Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Prop 18 - 1 Stretch Headband - The Sassy Olive Prop 18 - 1 Stretch Headband - The Sassy Olive
    Prop 18-1 Stretch Headband
    Prop 18-1 Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Strawberry Babies Stretch Headband - The Sassy Olive Strawberry Babies Stretch Headband - The Sassy Olive
    Strawberry Babies Stretch Headband
    Strawberry Babies Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pink Checkered Twist Headband - The Sassy Olive Pink Checkered Twist Headband - The Sassy Olive
    Pink Checkered Twist Headband
    Pink Checkered Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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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
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  • She/Her Pronouns Stretch Headband - The Sassy Olive She/Her Pronouns Stretch Headband - The Sassy Olive
    She/Her Pronouns Stretch Headband
    She/Her Pronouns Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • They/Them Pronouns Stretch Headband - The Sassy Olive They/Them Pronouns Stretch Headband
    They/Them Pronouns Stretch Headband
    They/Them Pronouns Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
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  • Proud Ally Stretch Headband - The Sassy Olive Proud Ally Stretch Headband - The Sassy Olive
    Proud Ally Stretch Headband
    Proud Ally Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • 1989 Stretch Headband - The Sassy Olive 1989 Stretch Headband - The Sassy Olive
    1989 Stretch Headband
    1989 Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • 1989 Top Knot Headband - The Sassy Olive 1989 Top Knot Headband - The Sassy Olive
    1989 Top Knot Headband
    1989 Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Fearless Stretch Headband - The Sassy Olive Fearless Stretch Headband - The Sassy Olive
    Fearless Stretch Headband
    Fearless Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Fearless Top Knot Headband - The Sassy Olive Fearless Top Knot Headband - The Sassy Olive
    Fearless Top Knot Headband
    Fearless Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Lover Stretch Headband - The Sassy Olive Lover Stretch Headband - The Sassy Olive
    Lover Stretch Headband
    Lover Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Lover Top Knot Headband - The Sassy Olive Lover Top Knot Headband - The Sassy Olive
    Lover Top Knot Headband
    Lover Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Red Cassette Stretch Headband - The Sassy Olive Red Cassette Stretch Headband - The Sassy Olive
    Red Cassette Stretch Headband
    Red Cassette Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
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  • Reputation Stretch Headband - The Sassy Olive Reputation Stretch Headband - The Sassy Olive
    Reputation Stretch Headband
    Reputation Stretch 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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  • Speak Now Stretch Headband - The Sassy Olive Speak Now Stretch Headband - The Sassy Olive
    Speak Now Stretch Headband
    Speak Now Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Speak Now Top Knot Headband - The Sassy Olive Speak Now Top Knot Headband - The Sassy Olive
    Speak Now Top Knot Headband
    Speak Now Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pickleball Everyday Stretch Headband - The Sassy Olive Pickleball Everyday Stretch Headband - The Sassy Olive
    Pickleball Everyday Stretch Headband
    Pickleball Everyday Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Olive Branch Stretch Headband - The Sassy Olive Olive Branch Stretch Headband - The Sassy Olive
    Olive Branch Stretch Headband
    Olive Branch Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Annotation Station Stretch Headband - The Sassy Olive Annotation Station Stretch Headband - The Sassy Olive
    Annotation Station Stretch Headband
    Annotation Station Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Book Club Stretch Headband - The Sassy Olive Book Club Stretch Headband - The Sassy Olive
    Book Club Stretch Headband
    Book Club Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Grimdark Stretch Headband - The Sassy Olive Grimdark Stretch Headband
    Grimdark Stretch Headband
    Grimdark Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Limited Edition Stretch Headband - The Sassy Olive Limited Edition Stretch Headband - The Sassy Olive
    Limited Edition Stretch Headband
    Limited Edition Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Readers Garden Stretch Headband - The Sassy Olive Readers Garden Stretch Headband
    Readers Garden Stretch Headband
    Readers Garden Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Sandworm Stretch Headband - The Sassy Olive Sandworm Stretch Headband - The Sassy Olive
    Sandworm Stretch Headband
    Sandworm Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Buzzard Banana Mushroom Random Ass Stretch - The Sassy Olive Buzzard Banana Mushroom Random Ass Stretch - The Sassy Olive
    Buzzard Banana Mushroom Random Ass Stretch Headband
    Buzzard Banana Mushroom Random Ass Stretch Headband
    Regular price
    $10.00
    Regular price
    Sale price
    $10.00
    Add to cart
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  • Blue Mountain Boho Buff - The Sassy Olive Blue Mountain Boho Buff - The Sassy Olive
    Blue Mountain Boho Buff
    Blue Mountain Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Feel the Fern Boho Buff - The Sassy Olive Feel the Fern Boho Buff - The Sassy Olive
    Feel the Fern Boho Buff
    Feel the Fern Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Bait Shop Boho Buff - The Sassy Olive Bait Shop Boho Buff - The Sassy Olive
    Bait Shop Boho Buff
    Bait Shop Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Lure Me In Boho Buff - The Sassy Olive Lure Me In Boho Buff - The Sassy Olive
    Lure Me In Boho Buff
    Lure Me In Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Red Mountains Boho Buff - The Sassy Olive Red Mountains Boho Buff - The Sassy Olive
    Red Mountains Boho Buff
    Red Mountains Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Similar products
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  • Dark Peace Boho Buff - The Sassy Olive Dark Peace Boho Buff - The Sassy Olive
    Dark Peace Boho Buff
    Dark Peace Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Poodle Stretch Headband - The Sassy Olive Poodle Stretch Headband - The Sassy Olive
    Poodle Stretch Headband
    Poodle Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Pug Stretch Headband - The Sassy Olive Pug Stretch Headband - The Sassy Olive
    Pug Stretch Headband
    Pug Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Rescued is My Favorite Breed Stretch Headband - The Sassy Olive Rescued is My Favorite Breed Stretch Headband - The Sassy Olive
    Rescued is My Favorite Breed Stretch Headband
    Rescued is My Favorite Breed 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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  • Dog Mom Stretch Headband - The Sassy Olive Dog Mom Stretch Headband - The Sassy Olive
    Dog Mom Stretch Headband
    Dog Mom Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Black Cat Energy Stretch Headband - The Sassy Olive Black Cat Energy Stretch Headband - The Sassy Olive
    Black Cat Energy Stretch Headband
    Black Cat Energy Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Calico Cat Stretch Headband - The Sassy Olive Calico Cat Stretch Headband - The Sassy Olive
    Calico Cat Stretch Headband
    Calico Cat Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Siamese Cat Stretch Headband - The Sassy Olive Siamese Cat Stretch Headband - The Sassy Olive
    Siamese Cat Stretch Headband
    Siamese Cat Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Tabby Cat Stretch Headband - The Sassy Olive Tabby Cat Stretch Headband - The Sassy Olive
    Tabby Cat Stretch Headband
    Tabby Cat 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
    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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  • 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
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  • WMU Stretch Headband - The Sassy Olive WMU Stretch Headband - The Sassy Olive
    WMU Stretch Headband
    WMU Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
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  • Pencil Bows Stretch Headband - The Sassy Olive Pencil Bows Stretch Headband - The Sassy Olive
    Pencil Bows Stretch Headband
    Pencil Bows Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Dinos in Space Stretch Headband - The Sassy Olive Dinos in Space Stretch Headband - The Sassy Olive
    Dinos in Space Stretch Headband
    Dinos in Space Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mushroom Crayons Stretch Headband - The Sassy Olive Mushroom Crayons Stretch Headband - The Sassy Olive
    Mushroom Crayons Stretch Headband
    Mushroom Crayons Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Y2K Teacher Stretch Headband - The Sassy Olive Y2K Teacher Stretch Headband - The Sassy Olive
    Y2K Teacher Stretch Headband
    Y2K Teacher Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Rad Shroomie Stretch Headband - The Sassy Olive Rad Shroomie Stretch Headband - The Sassy Olive
    Rad Shroomie Stretch Headband
    Rad Shroomie Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Autumn Arches Twist Headband - The Sassy Olive Autumn Arches Twist Headband - The Sassy Olive
    Autumn Arches Twist Headband
    Autumn Arches Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Copper Fields Twist Headband - The Sassy Olive Copper Fields Twist Headband - The Sassy Olive
    Copper Fields Twist Headband
    Copper Fields 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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  • Goldenrod Floral Twist Headband - The Sassy Olive Goldenrod Floral Twist Headband - The Sassy Olive
    Goldenrod Floral Twist Headband
    Goldenrod Floral 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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    Sold out
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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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  • Childless Cat Lady Stretch Headband - The Sassy Olive Childless Cat Lady Stretch Headband - The Sassy Olive
    Childless Cat Lady Stretch Headband
    Childless Cat Lady Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • I& I&
    I'm With Her Stretch Headband
    I'm With Her 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
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    $15.00
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  • Boho Bears Stretch Headband - The Sassy Olive Boho Bears Stretch Headband - The Sassy Olive
    Boho Bears Stretch Headband
    Boho Bears Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Foxy Stretch Headband - The Sassy Olive Foxy Stretch Headband - The Sassy Olive
    Foxy Stretch Headband
    Foxy Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Go Nuts Stretch Headband - The Sassy Olive Go Nuts Stretch Headband - The Sassy Olive
    Go Nuts Stretch Headband
    Go Nuts Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Hedgehogs and Mushrooms Stretch Headband - The Sassy Olive Hedgehogs and Mushrooms Stretch Headband - The Sassy Olive
    Hedgehogs and Mushrooms Stretch Headband
    Hedgehogs and Mushrooms Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Wolves Howl Stretch Headband - The Sassy Olive Wolves Howl Stretch Headband - The Sassy Olive
    Wolves Howl Stretch Headband
    Wolves Howl Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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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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  • Lions Pennant Stretch Headband - The Sassy Olive Lions Pennant Stretch Headband - The Sassy Olive
    Lions Pennant Stretch Headband
    Lions Pennant Stretch Headband
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  • Vintage Detroit Football Stretch Headband - The Sassy Olive Vintage Detroit Football Stretch Headband - The Sassy Olive
    Vintage Detroit Football Stretch Headband
    Vintage Detroit Football Stretch Headband
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  • Santonio Michigan State Stretch Headband - The Sassy Olive Santonio Michigan State Stretch Headband - The Sassy Olive
    Santonio Michigan State Stretch Headband
    Santonio Michigan State Stretch Headband
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  • Denard Robinson U of M Stretch Headband - The Sassy Olive Denard Robinson U of M Stretch Headband - The Sassy Olive
    Denard Robinson U of M Stretch Headband
    Denard Robinson U of M Stretch Headband
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  • Izzo Michigan State Stretch Headband - The Sassy Olive Izzo Michigan State Stretch Headband - The Sassy Olive
    Izzo Michigan State Stretch Headband
    Izzo Michigan State Stretch Headband
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  • Fucking Sunflowers Stretch Headband - The Sassy Olive Fucking Sunflowers Stretch Headband - The Sassy Olive
    Fucking Sunflowers Stretch Headband
    Fucking Sunflowers Stretch Headband
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  • Penis Plants Stretch Headband - The Sassy Olive Penis Plants Stretch Headband - The Sassy Olive
    Penis Plants Stretch Headband
    Penis Plants Stretch Headband
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    $15.00
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  • Basic Buffalo Plaid Stretch Headband - The Sassy Olive Basic Buffalo Plaid Stretch Headband - The Sassy Olive
    Basic Buffalo Plaid Stretch Headband
    Basic Buffalo Plaid Stretch Headband
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