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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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    • Trendy
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    • 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

  • Checkerboard Scrunchie Pack - The Sassy Olive Checkerboard Scrunchie Pack - The Sassy Olive
    Checkerboard Scrunchie Pack
    Checkerboard Scrunchie Pack
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Black Ivory Checker Wrap Headband - The Sassy Olive Black Ivory Checker Wrap Headband - The Sassy Olive
    Black Ivory Checker Wrap Headband
    Black Ivory Checker Wrap Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Burnt Orange Solid Wrap Headband - The Sassy Olive Burnt Orange Solid Wrap Headband - The Sassy Olive
    Burnt Orange Solid Wrap Headband
    Burnt Orange Solid Wrap Headband
    Regular price
    $18.00
    Regular price
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    $18.00
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  • Basic Buffalo Plaid Stretch Headband - The Sassy Olive Basic Buffalo Plaid Stretch Headband - The Sassy Olive
    Basic Buffalo Plaid Stretch Headband
    Basic Buffalo Plaid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • I Like Turtles Stretch Headband - The Sassy Olive I Like Turtles Stretch Headband - The Sassy Olive
    I Like Turtles Stretch Headband
    I Like Turtles Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Rabia Blue Stretch Headband - The Sassy Olive Rabia Blue Stretch Headband - The Sassy Olive
    Rabia Blue Stretch Headband
    Rabia Blue Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • D&D Dice Stretch Headband - The Sassy Olive D&D Dice Stretch Headband - The Sassy Olive
    D&D Dice Stretch Headband
    D&D Dice Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Bites, Mites, Flights, Lights Stretch Headband - The Sassy Olive Bites, Mites, Flights, Lights Stretch Headband - The Sassy Olive
    Bites, Mites, Flights, Lights Stretch Headband
    Bites, Mites, Flights, Lights Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Mermaid Mavens Stretch Headband - The Sassy Olive Mermaid Mavens Stretch Headband - The Sassy Olive
    Mermaid Mavens Stretch Headband
    Mermaid Mavens Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pickle Pals Stretch Headband - The Sassy Olive Pickle Pals Stretch Headband - The Sassy Olive
    Pickle Pals Stretch Headband
    Pickle Pals Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Overeasy Stretch Headband - The Sassy Olive Overeasy Stretch Headband - The Sassy Olive
    Overeasy Stretch Headband
    Overeasy Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Leighton Wrap Headband - The Sassy Olive Leighton Wrap Headband - The Sassy Olive
    Leighton Wrap Headband
    Leighton Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Merlot Burgundy Solid Wrap Headband - The Sassy Olive Merlot Burgundy Solid Wrap Headband - The Sassy Olive
    Merlot Burgundy Solid Wrap Headband
    Merlot Burgundy Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Mushroom Frogs Stretch Headband - The Sassy Olive Mushroom Frogs Stretch Headband - The Sassy Olive
    Mushroom Frogs Stretch Headband
    Mushroom Frogs Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Blue Galaxy Stretch Headband - The Sassy Olive Blue Galaxy Stretch Headband - The Sassy Olive
    Blue Galaxy Stretch Headband
    Blue Galaxy Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Sugar Babes Cupcakes Stretch Headband - The Sassy Olive Sugar Babes Cupcakes Stretch Headband - The Sassy Olive
    Sugar Babes Cupcakes Stretch Headband
    Sugar Babes Cupcakes Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Pateast Paisley Wrap Headband - The Sassy Olive Pateast Paisley Wrap Headband - The Sassy Olive
    Pateast Paisley Wrap Headband
    Pateast Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Floral Fables Stretch Headband - The Sassy Olive Floral Fables Stretch Headband - The Sassy Olive
    Floral Fables Stretch Headband
    Floral Fables Stretch Headband
    Regular price
    $15.00
    Regular price
    $15.00
    Sale price
    $15.00
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  • Neutral Flight Stretch Headband - The Sassy Olive Neutral Flight Stretch Headband - The Sassy Olive
    Neutral Flight Stretch Headband
    Neutral Flight Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Bell Bottoms Retro Floral Stretch Headband - The Sassy Olive Bell Bottoms Retro Floral Stretch Headband - The Sassy Olive
    Bell Bottoms Retro Floral Stretch Headband
    Bell Bottoms Retro Floral Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Rancher Bandana Paisley Stretch Headband - The Sassy Olive Rancher Bandana Paisley Stretch Headband - The Sassy Olive
    Rancher Bandana Paisley Stretch Headband
    Rancher Bandana Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Tommy& Tommy&
    Tommy's Donuts Stretch Headband
    Tommy's Donuts Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Overcome Stretch Headband - The Sassy Olive Overcome Stretch Headband - The Sassy Olive
    Overcome Stretch Headband
    Overcome Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sage that Shit Stretch Headband - The Sassy Olive Sage that Shit Stretch Headband - The Sassy Olive
    Sage that Shit Stretch Headband
    Sage that Shit Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Dachshund Stretch Headband - The Sassy Olive Dachshund Stretch Headband - The Sassy Olive
    Dachshund Stretch Headband
    Dachshund Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Berry Red Solid Wrap Headband - The Sassy Olive Berry Red Solid Wrap Headband - The Sassy Olive
    Berry Red Solid Wrap Headband
    Berry Red Solid Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Painted Expression Stretch Headband - The Sassy Olive Painted Expression Stretch Headband - The Sassy Olive
    Painted Expression Stretch Headband
    Painted Expression Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Fallen Autumn Stretch Headband - The Sassy Olive Fallen Autumn Stretch Headband - The Sassy Olive
    Fallen Autumn Stretch Headband
    Fallen Autumn Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Black Marble Stretch Headband - The Sassy Olive Black Marble Stretch Headband - The Sassy Olive
    Black Marble Stretch Headband
    Black Marble Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pink Sunflower Stretch Headband - The Sassy Olive Pink Sunflower Stretch Headband - The Sassy Olive
    Pink Sunflower Stretch Headband
    Pink Sunflower Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Foxy Stretch Headband - The Sassy Olive Foxy Stretch Headband - The Sassy Olive
    Foxy Stretch Headband
    Foxy Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Limited Edition Stretch Headband - The Sassy Olive Limited Edition Stretch Headband - The Sassy Olive
    Limited Edition Stretch Headband
    Limited Edition Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Lover Stretch Headband - The Sassy Olive Lover Stretch Headband - The Sassy Olive
    Lover Stretch Headband
    Lover Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Goatin& Goatin&
    Goatin' Around Stretch Headband
    Goatin' Around Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • I Like it Dirty Stretch Headband - The Sassy Olive I Like it Dirty Stretch Headband - The Sassy Olive
    I Like it Dirty Stretch Headband
    I Like it Dirty Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Firefighter Stretch Headband - The Sassy Olive Firefighter Stretch Headband - The Sassy Olive
    Firefighters White Stretch Headband
    Firefighters White Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Hoppin n Poppin Stretch Headband - The Sassy Olive Hoppin n Poppin Stretch Headband - The Sassy Olive
    Hoppin n Poppin Stretch Headband
    Hoppin n Poppin Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Any Fin Goes Stretch Headband - The Sassy Olive Any Fin Goes Stretch Headband - The Sassy Olive
    Any Fin Goes Stretch Headband
    Any Fin Goes Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Brace Yourself Stretch Headband - The Sassy Olive Brace Yourself Stretch Headband - The Sassy Olive
    Brace Yourself Stretch Headband
    Brace Yourself Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Breaker Bandana Paisley Wrap Headband - The Sassy Olive Breaker Bandana Paisley Wrap Headband - The Sassy Olive
    Breaker Bandana Paisley Wrap Headband
    Breaker Bandana Paisley Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
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  • Love Buds Stretch Headband - The Sassy Olive Love Buds Stretch Headband - The Sassy Olive
    Love Buds Stretch Headband
    Love Buds Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Garden Scribe Top Knot Headband - The Sassy Olive Garden Scribe Top Knot Headband - The Sassy Olive
    Garden Scribe Top Knot Headband
    Garden Scribe Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Ghostly Meadow Stretch Headband - The Sassy Olive Ghostly Meadow Stretch Headband - The Sassy Olive
    Ghostly Meadow Stretch Headband
    Ghostly Meadow Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Sunflower Patch Stretch Headband - The Sassy Olive Sunflower Patch Stretch Headband - The Sassy Olive
    Sunflower Patch Stretch Headband
    Sunflower Patch Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Balloon Dogs Stretch Headband - The Sassy Olive Balloon Dogs Stretch Headband - The Sassy Olive
    Balloon Dogs Stretch Headband
    Balloon Dogs Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Fuchsia Pink Solid Stretch Headband - The Sassy Olive Fuchsia Pink Solid Stretch Headband - The Sassy Olive
    Fuchsia Pink Solid Stretch Headband
    Fuchsia Pink Solid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
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  • Santonio Michigan State Stretch Headband - The Sassy Olive Santonio Michigan State Stretch Headband - The Sassy Olive
    Santonio Michigan State Stretch Headband
    Santonio Michigan State Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Arizona Blue Floral Stretch Headband - The Sassy Olive Arizona Blue Floral Stretch Headband - The Sassy Olive
    Arizona Blue Floral Stretch Headband
    Arizona Blue Floral Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • First Down Stretch Headband - The Sassy Olive First Down Stretch Headband - The Sassy Olive
    First Down Stretch Headband
    First Down Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Northern Lights Stretch Headband - The Sassy Olive Northern Lights Stretch Headband - The Sassy Olive
    Northern Lights Stretch Headband
    Northern Lights Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Wishbone 4 Stretch Headband - The Sassy Olive Wishbone 4 Stretch Headband - The Sassy Olive
    Wishbone 4 Stretch Headband
    Wishbone 4 Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Siren Song Stretch Headband - The Sassy Olive Siren Song Stretch Headband - The Sassy Olive
    Siren Song Stretch Headband
    Siren Song Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Ranch on Pizza Stretch Headband - The Sassy Olive Ranch on Pizza Stretch Headband - The Sassy Olive
    Ranch on Pizza Stretch Headband
    Ranch on Pizza Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Autism Awareness Stretch Headband - The Sassy Olive Autism Awareness Stretch Headband - The Sassy Olive
    Autism Awareness Stretch Headband
    Autism Awareness Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Chilly Penguins Stretch Headband - The Sassy Olive Chilly Penguins Stretch Headband - The Sassy Olive
    Chilly Penguins Stretch Headband
    Chilly Penguins Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • U of M Twist Headband - The Sassy Olive U of M Twist Headband - The Sassy Olive
    U of M Twist Headband
    U of M Twist Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
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  • Merlot Burgundy Solid Top Knot Headband - The Sassy Olive Merlot Burgundy Solid Top Knot Headband - The Sassy Olive
    Merlot Burgundy Solid Top Knot Headband
    Merlot Burgundy Solid Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Berry Red Solid Top Knot Headband - The Sassy Olive Berry Red Solid Top Knot Headband - The Sassy Olive
    Berry Red Solid Top Knot Headband
    Berry Red Solid Top Knot Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Night Sky Stretch Headband - The Sassy Olive Night Sky Stretch Headband - The Sassy Olive
    Night Sky Stretch Headband
    Night Sky Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Go Nuts Stretch Headband - The Sassy Olive Go Nuts Stretch Headband - The Sassy Olive
    Go Nuts Stretch Headband
    Go Nuts Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Speak Now Stretch Headband - The Sassy Olive Speak Now Stretch Headband - The Sassy Olive
    Speak Now Stretch Headband
    Speak Now Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Gridwork Tie Dye Stretch Headband - The Sassy Olive Gridwork Tie Dye Stretch Headband - The Sassy Olive
    Gridwork Tie Dye Stretch Headband
    Gridwork Tie Dye Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • Dark Peace Stretch Headband - The Sassy Olive Dark Peace Stretch Headband - The Sassy Olive
    Dark Peace Stretch Headband
    Dark Peace Stretch Headband
    Regular price
    $15.00
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    $15.00
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  • Silas Plaid Stretch Headband - The Sassy Olive Silas Plaid Stretch Headband - The Sassy Olive
    Silas Plaid Stretch Headband
    Silas Plaid Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • New Order Stretch Headband - The Sassy Olive New Order Stretch Headband - The Sassy Olive
    New Order Stretch Headband
    New Order Stretch Headband
    Regular price
    $15.00
    Regular price
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    $15.00
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  • U of M Nurse Stretch Headband - The Sassy Olive U of M Nurse Stretch Headband - The Sassy Olive
    U of M Nurse Stretch Headband
    U of M Nurse Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Goose Queen Stretch Headband - The Sassy Olive Goose Queen Stretch Headband - The Sassy Olive
    Goose Queen Stretch Headband
    Goose Queen Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Special Delivery Stretch Headband - The Sassy Olive Special Delivery Stretch Headband - The Sassy Olive
    Special Delivery Stretch Headband
    Special Delivery Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Pints Stretch Headband - The Sassy Olive Pints Stretch Headband - The Sassy Olive
    Pints Stretch Headband
    Pints Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
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  • Tetris Stretch Headband - The Sassy Olive Tetris Stretch Headband - The Sassy Olive
    Tetris Stretch Headband
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  • Vicountess Stretch Headband - The Sassy Olive Vicountess Stretch Headband - The Sassy Olive
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  • Leighton Carter Scrunchie Pack - The Sassy Olive Leighton Carter Scrunchie Pack - The Sassy Olive
    Leighton Carter Scrunchie Pack
    Leighton Carter Scrunchie Pack
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  • Readers Garden Wrap Headband - The Sassy Olive Readers Garden Wrap Headband - The Sassy Olive
    Readers Garden Wrap Headband
    Readers Garden Wrap Headband
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  • Joy Luxe Wrap Headband - The Sassy Olive Joy Luxe Wrap Headband - The Sassy Olive
    Joy Luxe Wrap Headband
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  • Frances Floral Wrap Headband - The Sassy Olive Frances Floral Wrap Headband - The Sassy Olive
    Frances Floral Wrap Headband
    Frances Floral Wrap Headband
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  • Navy Blue Solid Top Knot Headband - The Sassy Olive Navy Blue Solid Top Knot Headband - The Sassy Olive
    Navy Blue Solid Top Knot Headband
    Navy Blue Solid Top Knot Headband
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  • Michigan Wildflowers Stretch Headband - The Sassy Olive Michigan Wildflowers Stretch Headband - The Sassy Olive
    Michigan Wildflowers Stretch Headband
    Michigan Wildflowers Stretch Headband
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  • Fearless Stretch Headband - The Sassy Olive Fearless Stretch Headband - The Sassy Olive
    Fearless Stretch Headband
    Fearless Stretch Headband
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  • Caramel Brown Solid Stretch Headband - The Sassy Olive Caramel Brown Solid Stretch Headband - The Sassy Olive
    Caramel Brown Solid Stretch Headband
    Caramel Brown Solid Stretch Headband
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  • Light Blue Solid Stretch Headband - The Sassy Olive Light Blue Solid Stretch Headband - The Sassy Olive
    Light Blue Solid Stretch Headband
    Light Blue Solid Stretch Headband
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