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The Sassy OliveThe Sassy Olive
  • Shop
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    Shop by Type
    • Stretch Headbands
    • Top Knot Headbands
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    • Twist Headbands
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    • Slouchy Beanies
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    • Whimsical Cottagecore
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    • 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

  • Red Sunflowers Wrap Headband - The Sassy Olive Red Sunflowers Wrap Headband - The Sassy Olive
    Red Sunflowers Wrap Headband
    Red Sunflowers Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Peachy Garden Wrap Headband - The Sassy Olive Peachy Garden Wrap Headband - The Sassy Olive
    Peachy Garden Wrap Headband
    Peachy Garden Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Lavender Splatter Wrap Headband - The Sassy Olive Lavender Splatter Wrap Headband - The Sassy Olive
    Lavender Splatter Wrap Headband
    Lavender Splatter Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Zebra Print Wrap Headband - The Sassy Olive Zebra Print Wrap Headband - The Sassy Olive
    Zebra Print Wrap Headband
    Zebra Print Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Yellow Bell Floral Wrap Headband - The Sassy Olive Yellow Bell Floral Wrap Headband - The Sassy Olive
    Yellow Bell Floral Wrap Headband
    Yellow Bell Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Brown Cow Print Wrap Headband - The Sassy Olive Brown Cow Print Wrap Headband - The Sassy Olive
    Brown Cow Print Wrap Headband
    Brown Cow Print Wrap Headband
    Regular price
    $18.00
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    Sale price
    $18.00
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  • Dusty Blue Grey Solid Wrap Headband - The Sassy Olive Dusty Blue Grey Solid Wrap Headband - The Sassy Olive
    Dusty Blue Grey Solid Wrap Headband
    Dusty Blue Grey Solid Wrap Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Arizona Blue Floral Wrap Headband - The Sassy Olive Arizona Blue Floral Wrap Headband - The Sassy Olive
    Arizona Blue Floral Wrap Headband
    Arizona Blue Floral Wrap Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Shroom Bloom Twist Headband - The Sassy Olive Shroom Bloom Twist Headband - The Sassy Olive
    Shroom Bloom Twist Headband
    Shroom Bloom Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Paisley Dream Twist Headband - The Sassy Olive Paisley Dream Twist Headband - The Sassy Olive
    Paisley Dream Twist Headband
    Paisley Dream Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Mycelium Dreamy Top Knot Headband - The Sassy Olive Mycelium Dreamy Top Knot Headband - The Sassy Olive
    Mycelium Dreamy Top Knot Headband
    Mycelium Dreamy Top Knot Headband
    Regular price
    $15.00
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    $15.00
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  • Blueberry Lemon Squeeze Top Knot Headband Blueberry Lemon Squeeze Top Knot Headband - The Sassy Olive
    Blueberry Lemon Squeeze Top Knot Headband
    Blueberry Lemon Squeeze Top Knot Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Patchwork Top Knot Headband - The Sassy Olive Patchwork Top Knot Headband - The Sassy Olive
    Patchwork Top Knot Headband
    Patchwork Top Knot Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Banana Yellow Solid Top Knot Headband - The Sassy Olive Banana Yellow Solid Top Knot Headband - The Sassy Olive
    Banana Yellow Solid Top Knot Headband
    Banana Yellow Solid Top Knot Headband
    Regular price
    $15.00
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    $15.00
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  • Valentine’s Checker Stretch Headband - The Sassy Olive Valentine’s Checker Stretch Headband - The Sassy Olive
    Pink and Red Checker Stretch Headband
    Pink and Red Checker Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Spirit Wolf Stretch Headband - The Sassy Olive Spirit Wolf Stretch Headband - The Sassy Olive
    Spirit Wolf Stretch Headband
    Spirit Wolf Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Police Stretch Headband - The Sassy Olive Police Stretch Headband - The Sassy Olive
    Police Stretch Headband
    Police Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Chicago Cubs Stretch Headband - The Sassy Olive Chicago Cubs Stretch Headband - The Sassy Olive
    Chicago Cubs Stretch Headband
    Chicago Cubs Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Take Your Meds Stretch Headband - The Sassy Olive Take Your Meds Stretch Headband - The Sassy Olive
    Take Your Meds Stretch Headband
    Take Your Meds Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Speech Cue Cards Stretch Headband - The Sassy Olive Speech Cue Cards Stretch Headband - The Sassy Olive
    Speech Cue Cards Stretch Headband
    Speech Cue Cards Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Molar Magic Stretch Headband - The Sassy Olive Molar Magic Stretch Headband - The Sassy Olive
    Molar Magic Stretch Headband
    Molar Magic Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • EMS Stretch Headband - The Sassy Olive EMS Stretch Headband - The Sassy Olive
    EMS Stretch Headband
    EMS Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Cavity Cutie Stretch Headband - The Sassy Olive Cavity Cutie Stretch Headband - The Sassy Olive
    Cavity Cutie Stretch Headband
    Cavity Cutie Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mess of Mauve Stretch Headband - The Sassy Olive Mess of Mauve Stretch Headband - The Sassy Olive
    Mess of Mauve Stretch Headband
    Mess of Mauve Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
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  • Fitz Plaid Stretch Headband - The Sassy Olive Fitz Plaid Stretch Headband - The Sassy Olive
    Fitz Plaid Stretch Headband
    Fitz Plaid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Science Class Stretch Headband - The Sassy Olive Science Class Stretch Headband - The Sassy Olive
    Science Class Stretch Headband
    Science Class Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Lavender Volleyballs Stretch Headband - The Sassy Olive Lavender Volleyballs Stretch Headband - The Sassy Olive
    Lavender Volleyballs Stretch Headband
    Lavender Volleyballs Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Chem Class Stretch Headband - The Sassy Olive Chem Class Stretch Headband - The Sassy Olive
    Chem Class Stretch Headband
    Chem Class Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Bloom Blast Stretch Headband Bloom Blast Stretch Headband - The Sassy Olive
    Bloom Blast Stretch Headband
    Bloom Blast Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Apple Orchard Stretch Headband - The Sassy Olive Apple Orchard Stretch Headband - The Sassy Olive
    Apple Orchard Stretch Headband
    Apple Orchard Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Mint Stretch Headband - The Sassy Olive Mint Stretch Headband - The Sassy Olive
    Mint Green Stretch Headband
    Mint Green 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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  • 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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  • 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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  • Yorkshire Terrier Stretch Headband - The Sassy Olive Yorkshire Terrier Stretch Headband - The Sassy Olive
    Yorkshire Terrier Stretch Headband
    Yorkshire Terrier Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • King Charles Spaniel Stretch Headband - The Sassy Olive King Charles Spaniel Stretch Headband - The Sassy Olive
    King Charles Spaniel Stretch Headband
    King Charles Spaniel Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Davey& Davey&
    Davey's Heart Stretch Headband
    Davey's Heart Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Yellow and Maroon Stretch Headband - The Sassy Olive Yellow and Maroon Stretch Headband - The Sassy Olive
    Yellow and Maroon Stretch Headband
    Yellow and Maroon Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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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  • 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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  • Birdhouses Stretch Headband - The Sassy Olive Birdhouses Stretch Headband - The Sassy Olive
    Birdhouses Stretch Headband
    Birdhouses Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sun Bleached Splatter Tie Dye Boho Buff - The Sassy Olive Sun Bleached Splatter Tie Dye Boho Buff - The Sassy Olive
    Sun Bleached Splatter Tie Dye Boho Buff
    Sun Bleached Splatter Tie Dye Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Similar products
    Sold out
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  • Iced Coffee Tie Dye Boho Buff - The Sassy Olive Iced Coffee Tie Dye Boho Buff - The Sassy Olive
    Iced Coffee Tie Dye Boho Buff
    Iced Coffee Tie Dye Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Neutral Daisies Benzie Cap - The Sassy Olive Neutral Daisies Benzie Cap - The Sassy Olive
    Neutral Daisies Sassy Cap
    Neutral Daisies Sassy Cap
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Holy Cats Benzie Cap - The Sassy Olive Holy Cats Benzie Cap - The Sassy Olive
    Holy Cats Sassy Cap
    Holy Cats Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Breast Cancer Awareness Sassy Cap Breast Cancer Awareness Benzie Cap - The Sassy Olive
    Breast Cancer Awareness Sassy Cap
    Breast Cancer Awareness Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Black Marble Benzie Cap - The Sassy Olive Black Marble Benzie Cap - The Sassy Olive
    Black Marble Sassy Cap
    Black Marble Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Possums by CloudKBD Slouchy Beanie - The Sassy Olive Possums by CloudKBD Slouchy Beanie - The Sassy Olive
    Possums by CloudKBD Slouchy Beanie
    Possums by CloudKBD Slouchy Beanie
    Regular price
    $25.00
    Regular price
    Sale price
    $25.00
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  • Brown Tribal Feathers Slouchy Beanie - The Sassy Olive Brown Tribal Feathers Slouchy Beanie - The Sassy Olive
    Brown Tribal Feathers Slouchy Beanie
    Brown Tribal Feathers Slouchy Beanie
    Regular price
    $25.00
    Regular price
    Sale price
    $25.00
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  • Country Club Wrap Headband Country Club Wrap Headband - The Sassy Olive
    Country Club Wrap Headband
    Country Club Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Christmas Teal Paisley Wrap Headband - The Sassy Olive Christmas Teal Paisley Wrap Headband - The Sassy Olive
    Christmas Teal Paisley Wrap Headband
    Christmas Teal Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Rainbow Skulls Stretch Headband - The Sassy Olive Rainbow Skulls Stretch Headband - The Sassy Olive
    Rainbow Skulls Stretch Headband
    Rainbow Skulls Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Spooky Balloon Dogs Stretch Headband - The Sassy Olive Spooky Balloon Dogs Stretch Headband - The Sassy Olive
    Spooky Balloon Dogs Stretch Headband
    Spooky Balloon Dogs Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Peace, Love & Gumdrop Buttons Stretch Headband - The Sassy Olive Peace, Love & Gumdrop Buttons Stretch Headband - The Sassy Olive
    Peace, Love & Gumdrop Buttons Stretch Headband
    Peace, Love & Gumdrop Buttons Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
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    $15.00
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  • Holiday Hauler Stretch Headband - The Sassy Olive Holiday Hauler Stretch Headband - The Sassy Olive
    Holiday Hauler Stretch Headband
    Holiday Hauler Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
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  • Tangier Paisley Twist Headband - The Sassy Olive Tangier Paisley Twist Headband - The Sassy Olive
    Tangier Paisley Twist Headband
    Tangier Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Tangier Paisley Top Knot Headband Tangier Paisley Top Knot Headband - The Sassy Olive
    Tangier Paisley Top Knot Headband
    Tangier Paisley Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sugar Plum Paisley Wrap Headband - The Sassy Olive Sugar Plum Paisley Wrap Headband - The Sassy Olive
    Sugar Plum Paisley Wrap Headband
    Sugar Plum Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Smoke Paisley Wrap Headband - The Sassy Olive Smoke Paisley Wrap Headband - The Sassy Olive
    Smoke Paisley Wrap Headband
    Smoke Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Harvest Paisley Stretch Headband - The Sassy Olive Harvest Paisley Stretch Headband - The Sassy Olive
    Harvest Paisley Stretch Headband
    Harvest Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Dollhouse Paisley Wrap Headband - The Sassy Olive Dollhouse Paisley Wrap Headband - The Sassy Olive
    Dollhouse Paisley Wrap Headband
    Dollhouse Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Stars & Cherries Top Knot Headband - The Sassy Olive Stars & Cherries Top Knot Headband - The Sassy Olive
    Stars & Cherries Top Knot Headband
    Stars & Cherries Top Knot Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Stars & Cherries Stretch Headband Stars & Cherries Stretch Headband - The Sassy Olive
    Stars & Cherries Stretch Headband
    Stars & Cherries Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Patriotic Coastline Crab Stretch Headband - The Sassy Olive Patriotic Coastline Crab Stretch Headband - The Sassy Olive
    Patriotic Coastline Crab Stretch Headband
    Patriotic Coastline Crab Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Silver Solid Stretch Headband - The Sassy Olive Silver Solid Stretch Headband - The Sassy Olive
    Silver Solid Stretch Headband
    Silver Solid Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Leopard Pink Stretch Headband - The Sassy Olive Leopard Pink Stretch Headband - The Sassy Olive
    Leopard Pink Stretch Headband
    Leopard Pink Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Secret Garden Stretch Headband - The Sassy Olive Secret Garden Stretch Headband - The Sassy Olive
    Secret Garden Stretch Headband
    Secret Garden Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Antique Garden Stretch Headband - The Sassy Olive Antique Garden Stretch Headband - The Sassy Olive
    Antique Garden Stretch Headband
    Antique Garden Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Gardening Things Stretch Headband - The Sassy Olive Gardening Things Stretch Headband - The Sassy Olive
    Gardening Things Stretch Headband
    Gardening Things Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Bug Buddies Stretch Headband - The Sassy Olive Bug Buddies Stretch Headband - The Sassy Olive
    Bug Buddies Stretch Headband
    Bug Buddies Stretch Headband
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  • Lazy Lagoon Stretch Headband - The Sassy Olive Lazy Lagoon Stretch Headband - The Sassy Olive
    Lazy Lagoon Stretch Headband
    Lazy Lagoon Stretch Headband
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  • Blueberry Scrunchie Pack - The Sassy Olive Blueberry Scrunchie Pack - The Sassy Olive
    Blueberry Scrunchie Pack
    Blueberry Scrunchie Pack
    Regular price
    $18.00
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    $18.00
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  • Mint Chip Scrunchie Pack - The Sassy Olive Mint Chip Scrunchie Pack - The Sassy Olive
    Mint Chip Scrunchie Pack
    Mint Chip Scrunchie Pack
    Regular price
    $18.00
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  • Retro Stitches Wrap Headband - The Sassy Olive Retro Stitches Wrap Headband - The Sassy Olive
    Retro Stitches Wrap Headband
    Retro Stitches Wrap Headband
    Regular price
    $18.00
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  • Softly Sprung Wrap Headband - The Sassy Olive Softly Sprung Wrap Headband - The Sassy Olive
    Softly Sprung Wrap Headband
    Softly Sprung Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Sunlit Meadow Wrap Headband - The Sassy Olive Sunlit Meadow Wrap Headband - The Sassy Olive
    Sunlit Meadow Wrap Headband
    Sunlit Meadow Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Olive Medallions Wrap Headband - The Sassy Olive Olive Medallions Wrap Headband - The Sassy Olive
    Olive Medallions Wrap Headband
    Olive Medallions Wrap Headband
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    $18.00
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    $18.00
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  • Light Blue Solid Wrap Headband - The Sassy Olive Light Blue Solid Wrap Headband - The Sassy Olive
    Light Blue Solid Wrap Headband
    Light Blue Solid Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Banana Yellow Solid Wrap Headband - The Sassy Olive Banana Yellow Solid Wrap Headband - The Sassy Olive
    Banana Yellow Solid Wrap Headband
    Banana Yellow Solid Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Pretty Paws Twist Headband - The Sassy Olive Pretty Paws Twist Headband - The Sassy Olive
    Pretty Paws Twist Headband
    Pretty Paws Twist Headband
    Regular price
    $18.00
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    $18.00
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