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The Sassy OliveThe Sassy Olive
  • Shop
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    Shop by Type
    • Stretch Headbands
    • Top Knot Headbands
    • Wrap Headbands
    • Twist Headbands
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    • Slouchy Beanies
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    • Scrunchie Packs
    • All Styles
    Shop by Pattern
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    Shop by Vibe
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    • Y2K
    • Athletic
    • Minimal
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    • Whimsical Cottagecore
    • Punk
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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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Cart

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

  • Tendu Stretch Headband - The Sassy Olive Tendu Stretch Headband - The Sassy Olive
    Tendu Stretch Headband
    Tendu Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Let& Let&
    Let's Play Ball Stretch Headband
    Let's Play Ball Stretch Headband
    Regular price
    $15.00
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    Sale price
    $15.00
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  • Greyhound Stretch Headband - The Sassy Olive Greyhound Stretch Headband - The Sassy Olive
    Greyhound Stretch Headband
    Greyhound Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Dragon Croissant Pumpkin Toadlet Random Ass Stretch - The Sassy Olive Dragon Croissant Pumpkin Toadlet Random Ass Stretch - The Sassy Olive
    Dragon Croissant Pumpkin Toadlet Random Ass Stretch Headband
    Dragon Croissant Pumpkin Toadlet Random Ass Stretch Headband
    Regular price
    $10.00
    Regular price
    Sale price
    $10.00
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  • Bloody Mary Stretch Headband - The Sassy Olive Bloody Mary Stretch Headband - The Sassy Olive
    Bloody Mary Stretch Headband
    Bloody Mary Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Springer Spaniel Stretch Headband - The Sassy Olive Springer Spaniel Stretch Headband - The Sassy Olive
    Springer Spaniel Stretch Headband
    Springer Spaniel Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Red Hot Flames Stretch Headband - The Sassy Olive Red Hot Flames Stretch Headband - The Sassy Olive
    Red Hot Flames Stretch Headband
    Red Hot Flames 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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  • Tia Solid Pink Boho Buff - The Sassy Olive Tia Solid Pink Boho Buff - The Sassy Olive
    Tia Mauve Solid Pink Boho Buff
    Tia Mauve Solid Pink Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Lemon Grove Boho Buff - The Sassy Olive Lemon Grove Boho Buff - The Sassy Olive
    Lemon Grove Boho Buff
    Lemon Grove Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Berry Boho Buff (Red) - The Sassy Olive Berry Boho Buff (Red) - The Sassy Olive
    Berry Red Boho Buff
    Berry Red Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • DNR Stretch Headband - The Sassy Olive DNR Stretch Headband - The Sassy Olive
    DNR Stretch Headband
    DNR Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Red Hot Flames Boho Buff - The Sassy Olive Red Hot Flames Boho Buff - The Sassy Olive
    Red Hot Flames Boho Buff
    Red Hot Flames Boho Buff
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Similar products
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  • Land Before Time Benzie Cap - The Sassy Olive Land Before Time Benzie Cap - The Sassy Olive
    Land Before Time Sassy Cap
    Land Before Time Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Cutie Mushrooms Benzie Cap - The Sassy Olive Cutie Mushrooms Benzie Cap - The Sassy Olive
    Cutie Mushrooms Sassy Cap
    Cutie Mushrooms Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Classic Leopard Print Benzie Cap - The Sassy Olive Classic Leopard Print Benzie Cap - The Sassy Olive
    Classic Leopard Print Sassy Cap
    Classic Leopard Print Sassy Cap
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Chocolate Garden Benzie Cap - The Sassy Olive Chocolate Garden Benzie Cap - The Sassy Olive
    Chocolate Garden Sassy Cap
    Chocolate Garden Sassy Cap
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Starlit Woods Slouchy Beanie - The Sassy Olive Starlit Woods Slouchy Beanie - The Sassy Olive
    Starlit Woods Slouchy Beanie
    Starlit Woods Slouchy Beanie
    Regular price
    $25.00
    Regular price
    Sale price
    $25.00
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  • Elk Haven Slouchy Beanie - The Sassy Olive Elk Haven Slouchy Beanie - The Sassy Olive
    Elk Haven Slouchy Beanie
    Elk Haven Slouchy Beanie
    Regular price
    $25.00
    Regular price
    Sale price
    $25.00
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  • Garden Flower Top Knot Headband - The Sassy Olive Garden Flower Top Knot Headband - The Sassy Olive
    Garden Flower Top Knot Headband
    Garden Flower Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Folksy Floral Twist Headband - The Sassy Olive Folksy Floral Twist Headband - The Sassy Olive
    Folksy Floral Twist Headband
    Folksy Floral Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Folksy Floral Top Knot Headband - The Sassy Olive Folksy Floral Top Knot Headband - The Sassy Olive
    Folksy Floral Top Knot Headband
    Folksy Floral Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Cottagecore Mushrooms Twist Headband - The Sassy Olive Cottagecore Mushrooms Twist Headband - The Sassy Olive
    Cottagecore Mushrooms Twist Headband
    Cottagecore Mushrooms Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Cottagecore Mushrooms Stretch Headband - The Sassy Olive Cottagecore Mushrooms Stretch Headband - The Sassy Olive
    Cottagecore Mushrooms Stretch Headband
    Cottagecore Mushrooms Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Checker Love Stretch Headband - The Sassy Olive Checker Love Stretch Headband - The Sassy Olive
    Checker Love Stretch Headband
    Checker Love Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Brown Coquette Bows Top Knot Headband - The Sassy Olive Brown Coquette Bows Top Knot Headband - The Sassy Olive
    Brown Coquette Bows Top Knot Headband
    Brown Coquette Bows Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Michigan & Again Stretch Headband - The Sassy Olive Michigan & Again Stretch Headband - The Sassy Olive
    Michigan & Again Stretch Headband
    Michigan & Again Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Lions of Detroit Stretch Headband - The Sassy Olive Lions of Detroit Stretch Headband - The Sassy Olive
    Lions of Detroit Stretch Headband
    Lions of Detroit Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Heirloom Wrap Headband - The Sassy Olive Heirloom Wrap Headband - The Sassy Olive
    Heirloom Wrap Headband
    Heirloom Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Starry Holiday Wrap Headband - The Sassy Olive Starry Holiday Wrap Headband - The Sassy Olive
    Starry Holiday Wrap Headband
    Starry Holiday Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Simmer Pot Stretch Headband - The Sassy Olive Simmer Pot Stretch Headband - The Sassy Olive
    Simmer Pot Stretch Headband
    Simmer Pot Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Poinsettia Garden Stretch Headband - The Sassy Olive Poinsettia Garden Stretch Headband - The Sassy Olive
    Poinsettia Garden Stretch Headband
    Poinsettia Garden Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pine and Dandy Wrap Headband - The Sassy Olive Pine and Dandy Wrap Headband - The Sassy Olive
    Pine and Dandy Wrap Headband
    Pine and Dandy Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Mrs. Claus’ Garden Wrap Headband - The Sassy Olive Mrs. Claus’ Garden Wrap Headband - The Sassy Olive
    Mrs. Claus’ Garden Wrap Headband
    Mrs. Claus’ Garden Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Merry Medicine Stretch Headband - The Sassy Olive Merry Medicine Stretch Headband - The Sassy Olive
    Merry Medicine Stretch Headband
    Merry Medicine Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Hot Cocoa Snowman Wrap Headband - The Sassy Olive Hot Cocoa Snowman Wrap Headband - The Sassy Olive
    Hot Cocoa Snowman Wrap Headband
    Hot Cocoa Snowman Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Holiday Baking Stretch Headband - The Sassy Olive Holiday Baking Stretch Headband - The Sassy Olive
    Holiday Baking Stretch Headband
    Holiday Baking Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Dancer and Prancer Wrap Headband - The Sassy Olive Dancer and Prancer Wrap Headband - The Sassy Olive
    Dancer and Prancer Wrap Headband
    Dancer and Prancer Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Cranberry Christmas Blooms Wrap Headband - The Sassy Olive Cranberry Christmas Blooms Wrap Headband - The Sassy Olive
    Cranberry Christmas Blooms Wrap Headband
    Cranberry Christmas Blooms Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Chilly Checkers Wrap Headband - The Sassy Olive Chilly Checkers Wrap Headband - The Sassy Olive
    Chilly Checkers Wrap Headband
    Chilly Checkers Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Checkered Snowflakes Wrap Headband - The Sassy Olive Checkered Snowflakes Wrap Headband - The Sassy Olive
    Checkered Snowflakes Wrap Headband
    Checkered Snowflakes Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Cabin Cutie Wrap Headband - The Sassy Olive Cabin Cutie Wrap Headband - The Sassy Olive
    Cabin Cutie Wrap Headband
    Cabin Cutie Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Blue Snowflakes Stretch Headband - The Sassy Olive Blue Snowflakes Stretch Headband - The Sassy Olive
    Blue Snowflakes Stretch Headband
    Blue Snowflakes Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Preppy Halloween Stretch Headband - The Sassy Olive Preppy Halloween Stretch Headband - The Sassy Olive
    Preppy Halloween Stretch Headband
    Preppy Halloween Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Hearth & Home Wrap Headband - The Sassy Olive Hearth & Home Wrap Headband - The Sassy Olive
    Hearth & Home Wrap Headband
    Hearth & Home Wrap Headband
    Regular price
    $18.00
    Regular price
    $18.00
    Sale price
    $18.00
    Add to cart
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  • Wildfire Paisley Twist Headband - The Sassy Olive Wildfire Paisley Twist Headband - The Sassy Olive
    Wildfire Paisley Twist Headband
    Wildfire Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Sugar Plum Paisley Twist Headband - The Sassy Olive Sugar Plum Paisley Twist Headband - The Sassy Olive
    Sugar Plum Paisley Twist Headband
    Sugar Plum Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Sahara Paisley Twist Headband - The Sassy Olive Sahara Paisley Twist Headband - The Sassy Olive
    Sahara Paisley Twist Headband
    Sahara Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Porcelain Paisley Wrap Headband - The Sassy Olive Porcelain Paisley Wrap Headband - The Sassy Olive
    Porcelain Paisley Wrap Headband
    Porcelain Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Petals & Paisley Twist Headband - The Sassy Olive Petals & Paisley Twist Headband - The Sassy Olive
    Petals & Paisley Twist Headband
    Petals & Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Petals & Paisley Top Knot Headband - The Sassy Olive Petals & Paisley Top Knot Headband - The Sassy Olive
    Petals & Paisley Top Knot Headband
    Petals & Paisley Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Ocotillo Paisley Wrap Headband Ocotillo Paisley Wrap Headband - The Sassy Olive
    Ocotillo Paisley Wrap Headband
    Ocotillo Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Ocotillo Paisley Twist Headband - The Sassy Olive Ocotillo Paisley Twist Headband - The Sassy Olive
    Ocotillo Paisley Twist Headband
    Ocotillo Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Inkwell Paisley Twist Headband - The Sassy Olive Inkwell Paisley Twist Headband - The Sassy Olive
    Inkwell Paisley Twist Headband
    Inkwell Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Harvest Paisley Twist Headband - The Sassy Olive Harvest Paisley Twist Headband - The Sassy Olive
    Harvest Paisley Twist Headband
    Harvest Paisley Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Harvest Paisley Top Knot Headband - The Sassy Olive Harvest Paisley Top Knot Headband - The Sassy Olive
    Harvest Paisley Top Knot Headband
    Harvest Paisley Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • USA Goose Party Top Knot Headband - The Sassy Olive USA Goose Party Top Knot Headband - The Sassy Olive
    USA Goose Party Top Knot Headband
    USA Goose Party Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Surf’s Up Cowgirl Stretch Headband - The Sassy Olive Surf’s Up Cowgirl Stretch Headband - The Sassy Olive
    Surf’s Up Cowgirl Stretch Headband
    Surf’s Up Cowgirl Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Seashells & Spurs Stretch Headband - The Sassy Olive Seashells & Spurs Stretch Headband - The Sassy Olive
    Seashells & Spurs Stretch Headband
    Seashells & Spurs Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Howdy Aloha Stretch Headband - The Sassy Olive Howdy Aloha Stretch Headband - The Sassy Olive
    Howdy Aloha Stretch Headband
    Howdy Aloha Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Cowgirl Seahorse Stretch Headband - The Sassy Olive Cowgirl Seahorse Stretch Headband - The Sassy Olive
    Cowgirl Seahorse Stretch Headband
    Cowgirl Seahorse Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Rainforest Baby Twist Headband - The Sassy Olive Rainforest Baby Twist Headband - The Sassy Olive
    Rainforest Baby Twist Headband
    Rainforest Baby Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Silver Solid Wrap Headband - The Sassy Olive Silver Solid Wrap Headband - The Sassy Olive
    Silver Solid Wrap Headband
    Silver Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Tan Solid Stretch Headband - The Sassy Olive Tan Solid Stretch Headband - The Sassy Olive
    Tan Solid Stretch Headband
    Tan Solid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Walter Fish Boho Buff Headband - The Sassy Olive Walter Fish Boho Buff Headband - The Sassy Olive
    Walter Fish Boho Buff Headband
    Walter Fish Boho Buff Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Cornbread Cast Iron Stretch Headband - The Sassy Olive Cornbread Cast Iron Stretch Headband - The Sassy Olive
    Cornbread Cast Iron Stretch Headband
    Cornbread Cast Iron Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Tropical Pickle Ball Stretch Headband - The Sassy Olive Tropical Pickle Ball Stretch Headband - The Sassy Olive
    Tropical Pickle Ball Stretch Headband
    Tropical Pickle Ball Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pink Polka Dot Limes Stretch Headband - The Sassy Olive Pink Polka Dot Limes Stretch Headband - The Sassy Olive
    Pink Polka Dot Limes Stretch Headband
    Pink Polka Dot Limes Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Green Checker MSU Stretch Headband - The Sassy Olive Green Checker MSU Stretch Headband - The Sassy Olive
    Green Checker MSU Stretch Headband
    Green Checker MSU Stretch Headband
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  • Checkered U of M Stretch Headband - The Sassy Olive Checkered U of M Stretch Headband - The Sassy Olive
    Checkered U of M Stretch Headband
    Checkered U of M Stretch Headband
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    $15.00
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  • Secret Garden Top Knot Headband - The Sassy Olive Secret Garden Top Knot Headband - The Sassy Olive
    Secret Garden Top Knot Headband
    Secret Garden Top Knot Headband
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  • Icidem Top Knot Headband - The Sassy Olive Icidem Top Knot Headband - The Sassy Olive
    Icidem Top Knot Headband
    Icidem Top Knot Headband
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    $15.00
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  • Antique Garden Wrap Headband - The Sassy Olive Antique Garden Wrap Headband - The Sassy Olive
    Antique Garden Wrap Headband
    Antique Garden Wrap Headband
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    $18.00
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    $18.00
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  • Antique Garden Top Knot Headband - The Sassy Olive Antique Garden Top Knot Headband - The Sassy Olive
    Antique Garden Top Knot Headband
    Antique Garden Top Knot Headband
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    $15.00
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  • Sundown Petals Wrap Headband - The Sassy Olive Sundown Petals Wrap Headband - The Sassy Olive
    Sundown Petals Wrap Headband
    Sundown Petals Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Y2K Confetti Polka Dot Top Knot Headband Y2K Confetti Polka Dot Top Knot Headband
    Y2K Confetti Polka Dot Top Knot Headband
    Y2K Confetti Polka Dot Top Knot Headband
    Regular price
    $15.00
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    $15.00
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  • Vintage Cream Polka Dot Top Knot Headband Vintage Cream Polka Dot Top Knot Headband
    Vintage Cream Polka Dot Top Knot Headband
    Vintage Cream Polka Dot Top Knot Headband
    Regular price
    $15.00
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    $15.00
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  • Ballerina Headphone Castle Random Ass Sass Stretch Headband - The Sassy Olive Ballerina Headphone Castle Random Ass Sass Stretch Headband - The Sassy Olive
    Ballerina Headphone Castle Random Ass Sass Stretch Headband
    Ballerina Headphone Castle Random Ass Sass Stretch Headband
    Regular price
    $10.00
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    $10.00
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  • Lemon Grove Wrap Headband - The Sassy Olive Lemon Grove Wrap Headband - The Sassy Olive
    Lemon Grove Wrap Headband
    Lemon Grove Wrap Headband
    Regular price
    $18.00
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    $18.00
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  • Blossom Breeze Wrap Headband - The Sassy Olive Blossom Breeze Wrap Headband - The Sassy Olive
    Blossom Breeze Wrap Headband
    Blossom Breeze Wrap Headband
    Regular price
    $18.00
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