Skip to content
  • Shop
    Shop
    • Trending
      Trending
      • Newest Arrivals
      • Best Sellers
      • Canary Tales
      • Salty & Sweet
      • Vintage Show Pony
      • Cowboy Couture
      • Ditzy Floral
      • Shop All Headbands
    • Headband Styles
      Headband Styles
      • Sassy Stretch
      • Top Knot Sassy
      • Sassy Wrap
      • Sassy Twist
      • Boho Buff
      • Baby Sass
      • Shop All Headbands
    • Shop by Collection
      Shop by Collection
      • Sassy Medical Collection
      • Pride
      • Retro & 60s Headbands
      • The Michigan Collection
      • Book Club
      • Mommy & Me
      • Spooky Bitch
      • Random Ass Sass
      • Shop All Headbands
    • Shop by Pattern
      Shop by Pattern
      • Floral
      • Hobbies & Obsessions
      • Naughty & Swears
      • Occupations
      • Paisley
      • Plants & Animals
      • Solid Colors
      • Sports
      • Tie Dye
      • Western Prints
      • Shop All Headbands
    • More
      More
      • Gift Card
      • Clothes
      • Bundle Deals
      • Grab Bags
      • Scrunchie Packs
      • Your Vibe Bundle
      • Stickers
  • Customize
    Customize
    • Personalize & Pet Face
    • Custom Headbands
    • Special Request Product
  • Styling
    Styling
    • Stretch
    • Wrap
    • Top Knot
    • Twist
    • Short Hair
  • Fabric
  • Contact
    Contact
    • Contact Us
    • Retailers Near You
    • Fundraising
    • Artist Collaborations
    • Become an Affiliate
  • About
    About
    • Reviews
    • Press
    • Blog
    • About Landria
    • About the Team
  • Wholesale
    Wholesale
    • Variety Picks
Country/region
  • United States (USD $)
  • Åland Islands (EUR €)
  • Albania (ALL L)
  • Andorra (EUR €)
  • Austria (EUR €)
  • Belarus (USD $)
  • Belgium (EUR €)
  • Bosnia & Herzegovina (BAM КМ)
  • Bulgaria (BGN лв.)
  • Canada (CAD $)
  • Croatia (EUR €)
  • Czechia (CZK Kč)
  • Denmark (DKK kr.)
  • Estonia (EUR €)
  • Faroe Islands (DKK kr.)
  • Finland (EUR €)
  • France (EUR €)
  • Germany (EUR €)
  • Gibraltar (GBP £)
  • Greece (EUR €)
  • Guernsey (GBP £)
  • Hungary (HUF Ft)
  • Iceland (ISK kr)
  • Ireland (EUR €)
  • Isle of Man (GBP £)
  • Italy (EUR €)
  • Jersey (USD $)
  • Kosovo (EUR €)
  • Latvia (EUR €)
  • Liechtenstein (CHF CHF)
  • Lithuania (EUR €)
  • Luxembourg (EUR €)
  • Malta (EUR €)
  • Moldova (MDL L)
  • Monaco (EUR €)
  • Montenegro (EUR €)
  • Netherlands (EUR €)
  • North Macedonia (USD $)
  • Norway (USD $)
  • Poland (PLN zł)
  • Portugal (EUR €)
  • Romania (RON Lei)
  • Russia (USD $)
  • San Marino (EUR €)
  • Serbia (RSD РСД)
  • Slovakia (EUR €)
  • Slovenia (EUR €)
  • Spain (EUR €)
  • Svalbard & Jan Mayen (USD $)
  • Sweden (SEK kr)
  • Switzerland (CHF CHF)
  • Ukraine (UAH ₴)
  • United Kingdom (GBP £)
  • Vatican City (EUR €)
Log in
  • Facebook
  • Instagram
  • TikTok
  • YouTube
Country/region
  • United States (USD $)
  • Åland Islands (EUR €)
  • Albania (ALL L)
  • Andorra (EUR €)
  • Austria (EUR €)
  • Belarus (USD $)
  • Belgium (EUR €)
  • Bosnia & Herzegovina (BAM КМ)
  • Bulgaria (BGN лв.)
  • Canada (CAD $)
  • Croatia (EUR €)
  • Czechia (CZK Kč)
  • Denmark (DKK kr.)
  • Estonia (EUR €)
  • Faroe Islands (DKK kr.)
  • Finland (EUR €)
  • France (EUR €)
  • Germany (EUR €)
  • Gibraltar (GBP £)
  • Greece (EUR €)
  • Guernsey (GBP £)
  • Hungary (HUF Ft)
  • Iceland (ISK kr)
  • Ireland (EUR €)
  • Isle of Man (GBP £)
  • Italy (EUR €)
  • Jersey (USD $)
  • Kosovo (EUR €)
  • Latvia (EUR €)
  • Liechtenstein (CHF CHF)
  • Lithuania (EUR €)
  • Luxembourg (EUR €)
  • Malta (EUR €)
  • Moldova (MDL L)
  • Monaco (EUR €)
  • Montenegro (EUR €)
  • Netherlands (EUR €)
  • North Macedonia (USD $)
  • Norway (USD $)
  • Poland (PLN zł)
  • Portugal (EUR €)
  • Romania (RON Lei)
  • Russia (USD $)
  • San Marino (EUR €)
  • Serbia (RSD РСД)
  • Slovakia (EUR €)
  • Slovenia (EUR €)
  • Spain (EUR €)
  • Svalbard & Jan Mayen (USD $)
  • Sweden (SEK kr)
  • Switzerland (CHF CHF)
  • Ukraine (UAH ₴)
  • United Kingdom (GBP £)
  • Vatican City (EUR €)
The Sassy OliveThe Sassy Olive
  • Shop
    Trending
    • Newest Arrivals
    • Best Sellers
    • Canary Tales
    • Salty & Sweet
    • Vintage Show Pony
    • Cowboy Couture
    • Ditzy Floral
    • Shop All Headbands
    Headband Styles
    • Sassy Stretch
    • Top Knot Sassy
    • Sassy Wrap
    • Sassy Twist
    • Boho Buff
    • Baby Sass
    • Shop All Headbands
    Shop by Collection
    • Sassy Medical Collection
    • Pride
    • Retro & 60s Headbands
    • The Michigan Collection
    • Book Club
    • Mommy & Me
    • Spooky Bitch
    • Random Ass Sass
    • Shop All Headbands
    Shop by Pattern
    • Floral
    • Hobbies & Obsessions
    • Naughty & Swears
    • Occupations
    • Paisley
    • Plants & Animals
    • Solid Colors
    • Sports
    • Tie Dye
    • Western Prints
    • Shop All Headbands
    More
    • Gift Card
    • Clothes
    • Bundle Deals
    • Grab Bags
    • Scrunchie Packs
    • Your Vibe Bundle
    • Stickers
  • Customize
    • Personalize & Pet Face
    • Custom Headbands
    • Special Request Product
  • Styling
    • Stretch
    • Wrap
    • Top Knot
    • Twist
    • Short Hair
  • Fabric
  • Contact
    • Contact Us
    • Retailers Near You
    • Fundraising
    • Artist Collaborations
    • Become an Affiliate
  • About
    • Reviews
    • Press
    • Blog
    • About Landria
    • About the Team
  • Wholesale
    • Variety Picks
Log in
Cart
Access Denied
IMPORTANT! If you’re a store owner, please make sure you have Customer accounts enabled in your Store Admin, as you have customer based locks set up with EasyLockdown app. Enable Customer Accounts

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

The Sassy Stretch Headband is your new must-have accessory! Designed to fit every hair type and style, this ultra-soft, stretchy headband stays put all day—whether you’re rocking short hair, long locks, bangs, curls, or even a messy bun. Its snug yet comfortable fit makes it perfect for everything from casual days to workouts and beyond.

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

Headband Style Reset
Pattern Reset
Show more Show less
Sort by

780 products

Filter and sort
Filter and sort

780 products

Headband Style
Clear
Pattern
Clear
Clear
Clear all

780 products

  • Dragonfly Stretch - The Sassy Olive Dragonfly Stretch - The Sassy Olive
    Dragonfly Stretch Headband
    Dragonfly Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Green and White Stretch Headband - The Sassy Olive Green and White Stretch - The Sassy Olive
    Green and White Stretch Headband
    Green and White Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Muddy Jeep Wave Stretch Headband - The Sassy Olive Muddy Jeep Wave Stretch - The Sassy Olive
    Muddy Jeep Wave Stretch Headband
    Muddy Jeep Wave Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Michigan Beach Glass Stretch Headband - The Sassy Olive Michigan Beach Glass Stretch Headband - The Sassy Olive
    Michigan Beach Glass Stretch Headband
    Michigan Beach Glass Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Hidden Owl Stretch Headband - The Sassy Olive Hidden Owl Stretch Headband - The Sassy Olive
    Hidden Owl Stretch Headband
    Hidden Owl Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Maiden Mauve Stretch Headband - The Sassy Olive Maiden Mauve Stretch Headband - The Sassy Olive
    Maiden Mauve Stretch Headband
    Maiden Mauve Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Where& Where&
    Where's My Coffee Stretch Headband
    Where's My Coffee Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Sugar Babes Cupcakes Stretch Headband - The Sassy Olive Sugar Babes Cupcakes Stretch - The Sassy Olive
    Sugar Babes Cupcakes Stretch Headband
    Sugar Babes Cupcakes Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Black and Red Stretch Headband - The Sassy Olive Black and Red Stretch - The Sassy Olive
    Black and Red Stretch Headband
    Black and Red Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Chihuahua Stretch Headband - The Sassy Olive Chihuahua Stretch Headband - The Sassy Olive
    Chihuahua Stretch Headband
    Chihuahua Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Beagle Stretch Headband - The Sassy Olive Beagle Stretch Headband - The Sassy Olive
    Beagle Stretch Headband
    Beagle Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Monarch Garden Stretch Headband - The Sassy Olive Monarch Garden Stretch Headband - The Sassy Olive
    Monarch Garden Stretch Headband
    Monarch Garden Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
Show more
Invalid password
Enter

Hang With Us

  • Careers
  • Gift Cards
  • Events & Pop-Ups
  • Book a Private Party
  • Bridgefest Vendor Application
  • Allegan Events

Fine Print

  • Delivery & Returns
  • Points & Coupons Policy
  • Privacy Policy
  • Terms of Service

Wholesale

  • Wholesale Login
  • Wholesale Application
  • Wholesale FAQ

Get the Tea, be VIP

Apply for our free membership to receive exclusive deals, news, and events.

  • Facebook
  • Instagram
  • TikTok
  • YouTube
  • Follow us on social media!
© 2025, The Sassy Olive. All rights reserved.
  • Powered by Shopify
Country/region
  • United States (USD $)
  • Åland Islands (EUR €)
  • Albania (ALL L)
  • Andorra (EUR €)
  • Austria (EUR €)
  • Belarus (USD $)
  • Belgium (EUR €)
  • Bosnia & Herzegovina (BAM КМ)
  • Bulgaria (BGN лв.)
  • Canada (CAD $)
  • Croatia (EUR €)
  • Czechia (CZK Kč)
  • Denmark (DKK kr.)
  • Estonia (EUR €)
  • Faroe Islands (DKK kr.)
  • Finland (EUR €)
  • France (EUR €)
  • Germany (EUR €)
  • Gibraltar (GBP £)
  • Greece (EUR €)
  • Guernsey (GBP £)
  • Hungary (HUF Ft)
  • Iceland (ISK kr)
  • Ireland (EUR €)
  • Isle of Man (GBP £)
  • Italy (EUR €)
  • Jersey (USD $)
  • Kosovo (EUR €)
  • Latvia (EUR €)
  • Liechtenstein (CHF CHF)
  • Lithuania (EUR €)
  • Luxembourg (EUR €)
  • Malta (EUR €)
  • Moldova (MDL L)
  • Monaco (EUR €)
  • Montenegro (EUR €)
  • Netherlands (EUR €)
  • North Macedonia (USD $)
  • Norway (USD $)
  • Poland (PLN zł)
  • Portugal (EUR €)
  • Romania (RON Lei)
  • Russia (USD $)
  • San Marino (EUR €)
  • Serbia (RSD РСД)
  • Slovakia (EUR €)
  • Slovenia (EUR €)
  • Spain (EUR €)
  • Svalbard & Jan Mayen (USD $)
  • Sweden (SEK kr)
  • Switzerland (CHF CHF)
  • Ukraine (UAH ₴)
  • United Kingdom (GBP £)
  • Vatican City (EUR €)
Payment methods
  • Amazon
  • American Express
  • Apple Pay
  • Diners Club
  • Discover
  • Google Pay
  • JCB
  • Maestro
  • Mastercard
  • PayPal
  • Shop Pay
  • Union Pay
  • Venmo
  • Visa
Home
Menu
Search
Shop

Cart
Account
  • Choosing a selection results in a full page refresh.