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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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  • Rubber Duckies Stretch Headband - The Sassy Olive Rubber Duckies Stretch Headband - The Sassy Olive
    Rubber Duckies Stretch Headband
    Rubber Duckies Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Red Hot Peppers Stretch Headband - The Sassy Olive Red Hot Peppers Stretch Headband - The Sassy Olive
    Red Hot Peppers Stretch Headband
    Red Hot Peppers Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Rainbow Dinosaur Stretch Headband - The Sassy Olive Rainbow Dinosaur Stretch Headband - The Sassy Olive
    Rainbow Dinosaur Stretch Headband
    Rainbow Dinosaur Stretch Headband
    Regular price
    $15.00
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    $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
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    $15.00
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  • Ballerina Stretch Headband - The Sassy Olive Ballerina Stretch Headband - The Sassy Olive
    Ballerina Stretch Headband
    Ballerina Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • MSU Tie Dye Stretch Headband - The Sassy Olive MSU Tie Dye Stretch Headband - The Sassy Olive
    MSU Tie Dye Stretch Headband
    MSU Tie Dye Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Green Mandala MSU Stretch Headband - The Sassy Olive Green Mandala MSU Stretch Headband - The Sassy Olive
    Green Mandala MSU Stretch Headband
    Green Mandala MSU Stretch Headband
    Regular price
    $15.00
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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
    Regular price
    $15.00
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    $15.00
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  • U of M Polka Dots Stretch Headband - The Sassy Olive U of M Polka Dots Stretch Headband - The Sassy Olive
    U of M Polka Dots Stretch Headband
    U of M Polka Dots Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Mandala U of M Stretch Headband - The Sassy Olive Mandala U of M Stretch Headband - The Sassy Olive
    Mandala U of M Stretch Headband
    Mandala U of M Stretch Headband
    Regular price
    $15.00
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    $15.00
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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
    Regular price
    $15.00
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    $15.00
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  • Detroit Pistons Stretch Headband - The Sassy Olive Detroit Pistons Stretch Headband - The Sassy Olive
    Detroit Pistons Stretch Headband
    Detroit Pistons Stretch Headband
    Regular price
    $15.00
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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
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    $15.00
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  • Icidem Stretch Headband - The Sassy Olive Icidem Stretch Headband - The Sassy Olive
    Icidem Stretch Headband
    Icidem Stretch Headband
    Regular price
    $15.00
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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
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    $15.00
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  • Violet Veins Stretch Headband - The Sassy Olive Violet Veins Stretch Headband - The Sassy Olive
    Violet Veins Stretch Headband
    Violet Veins Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Wasabi Weave Stretch Headband - The Sassy Olive Wasabi Weave Stretch Headband - The Sassy Olive
    Wasabi Weave Stretch Headband
    Wasabi Weave Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Vintage Linoleum Stretch Headband - The Sassy Olive Vintage Linoleum Stretch Headband - The Sassy Olive
    Vintage Linoleum Stretch Headband
    Vintage Linoleum Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Sundown Petals Stretch Headband - The Sassy Olive Sundown Petals Stretch Headband - The Sassy Olive
    Sundown Petals Stretch Headband
    Sundown Petals Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Pure Paws Stretch Headband - The Sassy Olive Pure Paws Stretch Headband - The Sassy Olive
    Pure Paws Stretch Headband
    Pure Paws Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Garnet Grove Stretch Headband - The Sassy Olive Garnet Grove Stretch Headband - The Sassy Olive
    Garnet Grove Stretch Headband
    Garnet Grove Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Save the Turtles Stretch Headband - The Sassy Olive Save the Turtles Stretch Headband - The Sassy Olive
    Save the Turtles Stretch Headband
    Save the Turtles Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Little White Flowers Stretch Headband - The Sassy Olive Little White Flowers Stretch Headband - The Sassy Olive
    Little White Flowers Stretch Headband
    Little White Flowers Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Ditzy Pink Floral Stretch Headband - The Sassy Olive Ditzy Pink Floral Stretch Headband - The Sassy Olive
    Ditzy Pink Floral Stretch Headband
    Ditzy Pink Floral Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Green Bell Stretch Headband - The Sassy Olive Green Bell Stretch Headband - The Sassy Olive
    Green Bell Stretch Headband
    Green Bell Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Vegetable Garden Stretch Headband - The Sassy Olive Vegetable Garden Stretch Headband - The Sassy Olive
    Vegetable Garden Stretch Headband
    Vegetable Garden Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Tomato Tomato Stretch Headband - The Sassy Olive Tomato Tomato Stretch Headband - The Sassy Olive
    Tomato Tomato Stretch Headband
    Tomato Tomato Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Seed Packets Stretch Headband - The Sassy Olive Seed Packets Stretch Headband - The Sassy Olive
    Seed Packets Stretch Headband
    Seed Packets Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Jams and Jellies Stretch Headband - The Sassy Olive Jams and Jellies Stretch Headband - The Sassy Olive
    Jams and Jellies Stretch Headband
    Jams and Jellies Stretch Headband
    Regular price
    $15.00
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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
    Regular price
    $15.00
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    $15.00
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  • Wildflowers Garden Stretch Headband - The Sassy Olive Wildflowers Garden Stretch Headband - The Sassy Olive
    Wildflowers Garden Stretch Headband
    Wildflowers Garden Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Wild Roses Stretch Headband - The Sassy Olive Wild Roses Stretch Headband - The Sassy Olive
    Wild Roses Stretch Headband
    Wild Roses Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Rosehips and Petals Stretch Headband - The Sassy Olive Rosehips and Petals Stretch Headband - The Sassy Olive
    Rosehips and Petals Stretch Headband
    Rosehips and Petals Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Ready for a Hike Stretch Headband - The Sassy Olive Ready for a Hike Stretch Headband - The Sassy Olive
    Ready for a Hike Stretch Headband
    Ready for a Hike Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Morning Mountains Stretch Headband - The Sassy Olive Morning Mountains Stretch Headband - The Sassy Olive
    Morning Mountains Stretch Headband
    Morning Mountains Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Forget Me Not Floral Stretch Headband - The Sassy Olive Forget Me Not Floral Stretch Headband - The Sassy Olive
    Forget Me Not Floral Stretch Headband
    Forget Me Not Floral Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Forest of Ferns Stretch Headband - The Sassy Olive Forest of Ferns Stretch Headband - The Sassy Olive
    Forest of Ferns Stretch Headband
    Forest of Ferns Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Sea Garden Blue Stretch Headband - The Sassy Olive Sea Garden Blue Stretch Headband - The Sassy Olive
    Sea Garden Blue Stretch Headband
    Sea Garden Blue Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Dolce Coast Sage Stretch Headband - The Sassy Olive Dolce Coast Sage Stretch Headband - The Sassy Olive
    Dolce Coast Sage Stretch Headband
    Dolce Coast Sage Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Starstruck Coral Stretch Headband - The Sassy Olive Starstruck Coral Stretch Headband - The Sassy Olive
    Starstruck Coral Stretch Headband
    Starstruck Coral Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Sea Darling Stretch Headband - The Sassy Olive Sea Darling Stretch Headband - The Sassy Olive
    Sea Darling Stretch Headband
    Sea Darling Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Saltwater Sketch Stretch Headband - The Sassy Olive Saltwater Sketch Stretch Headband - The Sassy Olive
    Saltwater Sketch Stretch Headband
    Saltwater Sketch Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Palm Party Stretch Headband - The Sassy Olive Palm Party Stretch Headband - The Sassy Olive
    Palm Party Stretch Headband
    Palm Party Stretch Headband
    Regular price
    $15.00
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    Sale price
    $15.00
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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
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Boardwalk Blue Coastal Stretch Headband - The Sassy Olive Boardwalk Blue Coastal Stretch Headband - The Sassy Olive
    Boardwalk Blue Coastal Stretch Headband
    Boardwalk Blue Coastal Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Vicountess Stretch Headband - The Sassy Olive Vicountess Stretch Headband - The Sassy Olive
    Vicountess Stretch Headband
    Vicountess Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • The Cottage Stretch Headband - The Sassy Olive The Cottage Stretch Headband - The Sassy Olive
    The Cottage Stretch Headband
    The Cottage Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Spill the Tea Stretch Headband - The Sassy Olive Spill the Tea Stretch Headband - The Sassy Olive
    Spill the Tea Stretch Headband
    Spill the Tea Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Season’s Diamond Stretch Headband - The Sassy Olive Season’s Diamond Stretch Headband - The Sassy Olive
    Season’s Diamond Stretch Headband
    Season’s Diamond Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Queen C Stretch Headband - The Sassy Olive Queen C Stretch Headband - The Sassy Olive
    Queen C Stretch Headband
    Queen C Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Penelope Stretch Headband - The Sassy Olive Penelope Stretch Headband - The Sassy Olive
    Penelope Stretch Headband
    Penelope Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Masquerade Stretch Headband - The Sassy Olive Masquerade Stretch Headband - The Sassy Olive
    Masquerade Stretch Headband
    Masquerade Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Getaway Stretch Headband - The Sassy Olive Getaway Stretch Headband - The Sassy Olive
    Getaway Stretch Headband
    Getaway Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Gentle Reader Stretch Headband - The Sassy Olive Gentle Reader Stretch Headband - The Sassy Olive
    Gentle Reader Stretch Headband
    Gentle Reader Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Y2K Confetti Polka Dot Stretch Headband - The Sassy Olive Y2K Confetti Polka Dot Stretch Headband - The Sassy Olive
    Y2K Confetti Polka Dot Stretch Headband
    Y2K Confetti Polka Dot Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Y2K Blue & Brown Polka Dot Stretch Headband - The Sassy Olive Y2K Blue & Brown Polka Dot Stretch Headband - The Sassy Olive
    Y2K Blue & Brown Polka Dot Stretch Headband
    Y2K Blue & Brown Polka Dot Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Vintage Cream Polka Dot Stretch Headband - The Sassy Olive Vintage Cream Polka Dot Stretch Headband - The Sassy Olive
    Vintage Cream Polka Dot Stretch Headband
    Vintage Cream Polka Dot Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Victoria’s Pink Polka Dot Stretch Headband - The Sassy Olive Victoria’s Pink Polka Dot Stretch Headband - The Sassy Olive
    Victoria’s Pink Polka Dot Stretch Headband
    Victoria’s Pink Polka Dot Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Navy Polka Dot Stretch Headband - The Sassy Olive Navy Polka Dot Stretch Headband - The Sassy Olive
    Navy Polka Dot Stretch Headband
    Navy Polka Dot Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Classic Black Polka Dot Stretch Headband - The Sassy Olive Classic Black Polka Dot Stretch Headband - The Sassy Olive
    Classic Black Polka Dot Stretch Headband
    Classic Black Polka Dot Stretch 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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  • No Ice Stretch Headband - The Sassy Olive No Ice Stretch Headband - The Sassy Olive
    No Ice Stretch Headband
    No Ice Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Resist Stretch Headband - The Sassy Olive Resist Stretch Headband - The Sassy Olive
    Resist Stretch Headband
    Resist Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Big Fan of Human Rights Stretch Headband - The Sassy Olive Big Fan of Human Rights Stretch Headband - The Sassy Olive
    Big Fan of Human Rights Stretch Headband
    Big Fan of Human Rights Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Fuck ICE Stretch Headband - The Sassy Olive Fuck ICE Stretch Headband - The Sassy Olive
    Fuck ICE Stretch Headband
    Fuck ICE Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • It’s Okay to Punch Nazis Stretch Headband - The Sassy Olive It’s Okay to Punch Nazis Stretch Headband - The Sassy Olive
    It’s Okay to Punch Nazis Stretch Headband
    It’s Okay to Punch Nazis Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Morel Mushroom Stretch Headband - The Sassy Olive Morel Mushroom Stretch Headband - The Sassy Olive
    Morel Mushroom Stretch Headband
    Morel Mushroom Stretch Headband
    Regular price
    $15.00
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  • Chicken of the Woods Stretch Headband - The Sassy Olive Chicken of the Woods Stretch Headband - The Sassy Olive
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  • Chanterelle Stretch Headband - The Sassy Olive Chanterelle Stretch Headband
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  • DNR Stretch Headband - The Sassy Olive DNR Stretch Headband - The Sassy Olive
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  • Chirp Charm Stretch Headband - The Sassy Olive Chirp Charm Stretch Headband - The Sassy Olive
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  • Porcelain Plate Robins Stretch Headband - The Sassy Olive Porcelain Plate Robins Stretch Headband - The Sassy Olive
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  • Flap Happy Goose Stretch Headband - The Sassy Olive Flap Happy Goose Stretch Headband - The Sassy Olive
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  • Chicken Chat Stretch Headband - The Sassy Olive Chicken Chat Stretch Headband - The Sassy Olive
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  • Cardinal Woods Stretch Headband - The Sassy Olive Cardinal Woods Stretch Headband - The Sassy Olive
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  • Birdhouses Stretch Headband - The Sassy Olive Birdhouses Stretch Headband - The Sassy Olive
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  • Apple Blossom Robins Stretch Headband - The Sassy Olive Apple Blossom Robins Stretch Headband - The Sassy Olive
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  • Tree Stuff by CloudKBD Stretch Headband - The Sassy Olive Tree Stuff by CloudKBD Stretch Headband - The Sassy Olive
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  • Raccoons by CloudKBD Stretch Headband - The Sassy Olive Raccoons by CloudKBD Stretch Headband - The Sassy Olive
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