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

  • 60& 60&
    60's Picnic Blanket Stretch Headband
    60's Picnic Blanket Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Fire Fighter Stretch - The Sassy Olive Fire Fighter Stretch - The Sassy Olive
    Firefighter Stretch Headband
    Firefighter Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Dude, Where& Dude, Where&
    Dude, Where's My Car? Stretch Headband
    Dude, Where's My Car? Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Bites, Mites, Flights, Lights Stretch Headband - The Sassy Olive Bites, Mites, Flights, Lights Stretch - The Sassy Olive
    Bites, Mites, Flights, Lights Stretch Headband
    Bites, Mites, Flights, Lights Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Garden Finds Stretch Headband - The Sassy Olive Garden Finds Stretch Headband - The Sassy Olive
    Garden Finds Stretch Headband
    Garden Finds Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Michigan State Football Stretch Headband - The Sassy Olive Michigan State Football Stretch Headband - The Sassy Olive
    Michigan State Football Stretch Headband
    Michigan State Football Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Funky Fresh Paisley Stretch Headband - The Sassy Olive Funky Fresh Paisley Stretch Headband - The Sassy Olive
    Funky Fresh Paisley Stretch Headband
    Funky Fresh Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • 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
    Add to cart
    Quick view
  • Tetris Stretch Headband - The Sassy Olive Tetris Stretch Headband - The Sassy Olive
    Tetris Stretch Headband
    Tetris Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Tube Socks Tie Dye Stretch Headband - The Sassy Olive Tube Socks Tie Dye Stretch Headband - The Sassy Olive
    Tube Socks Tie Dye Stretch Headband
    Tube Socks Tie Dye Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Wishbone 3 Stretch Headband - The Sassy Olive Wishbone 3 Stretch Headband - The Sassy Olive
    Wishbone 3 Stretch Headband
    Wishbone 3 Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Shelves of Spells Stretch Headband - The Sassy Olive Shelves of Spells Stretch Headband - The Sassy Olive
    Shelves of Spells Stretch Headband
    Shelves of Spells 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.