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Collection: Sassy Stretch Headband – The Ultimate Fit for Every Style

The Sassy Stretch Headband is our most popular style. Designed for everyday wear, these handmade headbands are made from buttery soft, stretchy fabric that stays in place without being too tight.

We design and print our fabrics in-house in Michigan, which means you won’t find these patterns just anywhere.  Great for girls, guys, and anyone who loves fun, functional headbands.

Want to explore different ways to wear it? Check out our Sassy Stretch Styling Guide for tips and inspiration!

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  • Angela’s Floral Green Stretch Headband - The Sassy Olive Angela’s Floral Green Stretch Headband - The Sassy Olive
    Floral by Scribbler Experiment Stretch Headband
    Floral by Scribbler Experiment Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
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    $15.00
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  • Country Club Stretch Headband - The Sassy Olive Country Club Stretch Headband - The Sassy Olive
    Country Club Stretch Headband
    Country Club Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Melted Sherbet Stretch Headband - The Sassy Olive Melted Sherbet Stretch Headband - The Sassy Olive
    Melted Sherbet Stretch Headband
    Melted Sherbet Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Rainbow Cattle Ranch Stretch Headband - The Sassy Olive Rainbow Cattle Ranch Stretch Headband - The Sassy Olive
    Rainbow Cattle Ranch Stretch Headband
    Rainbow Cattle Ranch Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Heirloom Stretch Headband - The Sassy Olive Heirloom Stretch Headband - The Sassy Olive
    Heirloom Stretch Headband
    Heirloom Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Sunflower Color Party Stretch Headband - The Sassy Olive Sunflower Color Party Stretch Headband - The Sassy Olive
    Sunflower Color Party Stretch Headband
    Sunflower Color Party Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Purrception Stretch Headband - The Sassy Olive Purrception Stretch Headband - The Sassy Olive
    Purrception Stretch Headband
    Purrception Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Patch o’ Pansies Stretch Headband - The Sassy Olive Patch o’ Pansies Stretch Headband
    Patch o’ Pansies Stretch Headband
    Patch o’ Pansies Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Mediterranean Vibes Stretch Headband - The Sassy Olive Mediterranean Vibes Stretch Headband - The Sassy Olive
    Mediterranean Vibes Stretch Headband
    Mediterranean Vibes Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Confetti Kitties Stretch Headband - The Sassy Olive Confetti Kitties Stretch Headband - The Sassy Olive
    Confetti Kitties Stretch Headband
    Confetti Kitties Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Atomic Cats Stretch Headband - The Sassy Olive Atomic Cats Stretch Headband - The Sassy Olive
    Atomic Cats Stretch Headband
    Atomic Cats Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Winter Greens Stretch Headband - The Sassy Olive Winter Greens Stretch Headband - The Sassy Olive
    Winter Greens Stretch Headband
    Winter Greens Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Snowmany Snowmen Stretch Headband - The Sassy Olive Snowmany Snowmen Stretch Headband - The Sassy Olive
    Snowmany Snowmen Stretch Headband
    Snowmany Snowmen Stretch Headband
    Regular price
    $15.00
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    $15.00
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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
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    $15.00
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  • Rainbow Forest Stretch Headband - The Sassy Olive Rainbow Forest Stretch Headband - The Sassy Olive
    Rainbow Forest Stretch Headband
    Rainbow Forest Stretch Headband
    Regular price
    $15.00
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    $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
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    $15.00
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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
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    $15.00
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  • Merry Jeepmas Stretch Headband - The Sassy Olive Merry Jeepmas Stretch Headband - The Sassy Olive
    Merry Jeepmas Stretch Headband
    Merry Jeepmas Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Hot Toddy Stretch Headband - The Sassy Olive Hot Toddy Stretch Headband - The Sassy Olive
    Hot Toddy Stretch Headband
    Hot Toddy Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Holly Garland Stretch Headband - The Sassy Olive Holly Garland Stretch Headband - The Sassy Olive
    Holly Garland Stretch Headband
    Holly Garland Stretch Headband
    Regular price
    $15.00
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    $15.00
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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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  • Hanukkah Chanukkah Stretch Headband - The Sassy Olive Hanukkah Chanukkah Stretch Headband - The Sassy Olive
    Hanukkah Chanukkah Stretch Headband
    Hanukkah Chanukkah Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Grey Reindeer Sweater Stretch Headband - The Sassy Olive Grey Reindeer Sweater Stretch Headband - The Sassy Olive
    Grey Reindeer Sweater Stretch Headband
    Grey Reindeer Sweater Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Gingerbread Icing Stretch Headband - The Sassy Olive Gingerbread Icing Stretch Headband - The Sassy Olive
    Gingerbread Icing Stretch Headband
    Gingerbread Icing Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Cranberry Christmas Blooms Stretch Headband - The Sassy Olive Cranberry Christmas Blooms Stretch Headband - The Sassy Olive
    Cranberry Christmas Blooms Stretch Headband
    Cranberry Christmas Blooms Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Christmas Porch Goose Stretch Headband - The Sassy Olive Christmas Porch Goose Stretch Headband - The Sassy Olive
    Christmas Porch Goose Stretch Headband
    Christmas Porch Goose Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • BooJee Christmas Stretch Headband - The Sassy Olive BooJee Christmas Stretch Headband - The Sassy Olive
    BooJee Christmas Stretch Headband
    BooJee Christmas Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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
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    $15.00
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  • Atomic Santa Stretch Headband - The Sassy Olive Atomic Santa Stretch Headband - The Sassy Olive
    Atomic Santa Stretch Headband
    Atomic Santa Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Spooky Italian Summer Stretch Headband - The Sassy Olive Spooky Italian Summer Stretch Headband - The Sassy Olive
    Spooky Italian Summer Stretch Headband
    Spooky Italian Summer Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $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
    Sale price
    $15.00
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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
    Sale price
    $15.00
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  • Rainbow Sheet Ghosts Stretch Headband - The Sassy Olive Rainbow Sheet Ghosts Stretch Headband - The Sassy Olive
    Rainbow Sheet Ghosts Stretch Headband
    Rainbow Sheet Ghosts 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
    Add to cart
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  • Creepy Cones Stretch Headband - The Sassy Olive Creepy Cones Stretch Headband - The Sassy Olive
    Creepy Cones Stretch Headband
    Creepy Cones Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Cute Spooky Cats Stretch Headband - The Sassy Olive Cute Spooky Cats Stretch Headband - The Sassy Olive
    Cute Spooky Cats Stretch Headband
    Cute Spooky Cats Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Moonlit Macabre Stretch Headband - The Sassy Olive Moonlit Macabre Stretch Headband - The Sassy Olive
    Moonlit Macabre Stretch Headband
    Moonlit Macabre Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Wildfire Paisley Stretch Headband - The Sassy Olive Wildfire Paisley Stretch Headband - The Sassy Olive
    Wildfire Paisley Stretch Headband
    Wildfire Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Tangier Paisley Stretch Headband - The Sassy Olive Tangier Paisley Stretch Headband - The Sassy Olive
    Tangier Paisley Stretch Headband
    Tangier Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sugar Plum Paisley Stretch Headband - The Sassy Olive Sugar Plum Paisley Stretch Headband - The Sassy Olive
    Sugar Plum Paisley Stretch Headband
    Sugar Plum Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Smoke Paisley Stretch Headband Smoke Paisley Stretch Headband
    Smoke Paisley Stretch Headband
    Smoke Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sahara Paisley Stretch Headband Sahara Paisley Stretch Headband - The Sassy Olive
    Sahara Paisley Stretch Headband
    Sahara Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Porcelain Paisley Stretch Headband - The Sassy Olive Porcelain Paisley Stretch Headband - The Sassy Olive
    Porcelain Paisley Stretch Headband
    Porcelain Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Petals & Paisley Stretch Headband - The Sassy Olive Petals & Paisley Stretch Headband - The Sassy Olive
    Petals & Paisley Stretch Headband
    Petals & Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Ocotillo Paisley Stretch Headband - The Sassy Olive Ocotillo Paisley Stretch Headband - The Sassy Olive
    Ocotillo Paisley Stretch Headband
    Ocotillo Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Inkwell Paisley Stretch Headband - The Sassy Olive Inkwell Paisley Stretch Headband - The Sassy Olive
    Inkwell Paisley Stretch Headband
    Inkwell Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Henna Paisley Stretch Headband - The Sassy Olive Henna Paisley Stretch Headband - The Sassy Olive
    Henna Paisley Stretch Headband
    Henna Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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 Stretch Headband - The Sassy Olive Dollhouse Paisley Stretch Headband - The Sassy Olive
    Dollhouse Paisley Stretch Headband
    Dollhouse Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Red, White & Blue Tie - Dye Stretch Headband - The Sassy Olive Red, White & Blue Tie - Dye Stretch Headband - The Sassy Olive
    Red, White & Blue Tie-Dye Stretch Headband
    Red, White & Blue Tie-Dye Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • USA Goose Party Stretch Headband - The Sassy Olive USA Goose Party Stretch Headband - The Sassy Olive
    USA Goose Party Stretch Headband
    USA Goose Party Stretch 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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  • Picnic With Uncle Sam Stretch Headband - The Sassy Olive Picnic With Uncle Sam Stretch Headband - The Sassy Olive
    Picnic With Uncle Sam Stretch Headband
    Picnic With Uncle Sam Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Freedom Pop Stretch Headband - The Sassy Olive Freedom Pop Stretch Headband - The Sassy Olive
    Freedom Pop Stretch Headband
    Freedom Pop Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Fireworks Stretch Headband - The Sassy Olive Fireworks Stretch Headband - The Sassy Olive
    Fireworks Stretch Headband
    Fireworks Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Yeehaw Dolphins Stretch Headband - The Sassy Olive Yeehaw Dolphins Stretch Headband - The Sassy Olive
    Yeehaw Dolphins Stretch Headband
    Yeehaw Dolphins Stretch 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
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    $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
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    $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
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    $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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  • 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
    Regular price
    Sale price
    $15.00
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  • Blush Pink Solid Stretch Headband - The Sassy Olive Blush Pink Solid Stretch Headband - The Sassy Olive
    Blush Pink Solid Stretch Headband
    Blush Pink Solid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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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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  • Hawaiian Blue Solid Stretch Headband - The Sassy Olive Hawaiian Blue Solid Stretch Headband - The Sassy Olive
    Hawaiian Blue Solid Stretch Headband
    Hawaiian Blue Solid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Turkey Mount Stretch Headband - The Sassy Olive Turkey Mount Stretch Headband - The Sassy Olive
    Turkey Mount Stretch Headband
    Turkey Mount Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Rodeo Pups Stretch Headband - The Sassy Olive Rodeo Pups Stretch Headband - The Sassy Olive
    Rodeo Pups Stretch Headband
    Rodeo Pups Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Punchy Dreams Stretch Headband - The Sassy Olive Punchy Dreams Stretch Headband - The Sassy Olive
    Punchy Dreams Stretch Headband
    Punchy Dreams Stretch Headband
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  • Prickly Pear Cactus Stretch Headband - The Sassy Olive Prickly Pear Cactus Stretch Headband - The Sassy Olive
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    Prickly Pear Cactus Stretch Headband
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  • Dive Bar Stretch Headband - The Sassy Olive Dive Bar Stretch Headband - The Sassy Olive
    Dive Bar Stretch Headband
    Dive Bar Stretch Headband
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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
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  • Dark Butterfly Noir Stretch Headband - The Sassy Olive Dark Butterfly Noir Stretch Headband - The Sassy Olive
    Dark Butterfly Noir Stretch Headband
    Dark Butterfly Noir Stretch Headband
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  • Boot Scootin Stretch Headband - The Sassy Olive Boot Scootin Stretch Headband - The Sassy Olive
    Boot Scootin Stretch Headband
    Boot Scootin Stretch Headband
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  • Horses F1 Casino Random Ass Sass Stretch Headband - The Sassy Olive Horses F1 Casino Random Ass Sass Stretch Headband - The Sassy Olive
    Horses F1 Casino Random Ass Sass Stretch Headband
    Horses F1 Casino Random Ass Sass Stretch Headband
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  • Cameras Stretch Headband - The Sassy Olive Cameras Stretch Headband - The Sassy Olive
    Cameras Stretch Headband
    Cameras Stretch Headband
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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
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  • Red Mandala Love Stretch Headband - The Sassy Olive Red Mandala Love Stretch Headband - The Sassy Olive
    Red Mandala Love Stretch Headband
    Red Mandala Love Stretch Headband
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  • Mod Pastel Flowers Stretch Headband - The Sassy Olive Mod Pastel Flowers Stretch Headband - The Sassy Olive
    Mod Pastel Flowers Stretch Headband
    Mod Pastel Flowers Stretch Headband
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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
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  • Sugar Cones Stretch Headband - The Sassy Olive Sugar Cones Stretch Headband - The Sassy Olive
    Sugar Cones Stretch Headband
    Sugar Cones Stretch Headband
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