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: Outdoorsy

Whether she’s camping under the stars or just manifesting cabin-core from her porch, these stretch headbands are made for the wild at heart. Think bugs, maps, mountains, and s’mores—all the best parts of getting lost in nature (without the mosquito bites). Every print is a little nod to fresh air, messy buns, and muddy boots. Perfect for hiking, hammock naps, and accidentally starting a fire while trying to light a marshmallow.

Headband Style Reset
Pattern Reset
Show more Show less
Sort by

92 products

Filter and sort
Filter and sort

92 products

Headband Style
Clear
Pattern
Clear
Clear
Clear all

92 products

  • Cactus Cuervo Stretch Headband - The Sassy Olive Cactus Cuervo Stretch Headband - The Sassy Olive
    Cactus Cuervo Stretch Headband
    Cactus Cuervo Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • 10,000 to 1 Stretch Headband - The Sassy Olive 10,000 to 1 Stretch Headband - The Sassy Olive
    Shamrock Stretch Headband
    Shamrock Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Airstream Stretch Headband - The Sassy Olive Airstream Stretch Headband - The Sassy Olive
    Airstream Stretch Headband
    Airstream Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Madie Mushroom Stretch - The Sassy Olive Madie Mushroom Stretch - The Sassy Olive
    Madie's Mushroom Stretch Headband
    Madie's Mushroom Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Happy Camper Stretch Headband - The Sassy Olive Happy Camper Stretch Headband - The Sassy Olive
    Happy Camper Stretch Headband
    Happy Camper Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • I& I&
    I'm a Succa for You Wrap Headband
    I'm a Succa for You Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Purple Galaxy Stretch Headband - The Sassy Olive Purple Galaxy Stretch Headband - The Sassy Olive
    Purple Galaxy Stretch Headband
    Purple Galaxy Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • MonsteraStretch Headband - The Sassy Olive MonsteraStretch Headband - The Sassy Olive
    Monstera Stretch Headband
    Monstera Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • It& It&
    It's Just a Phase Stretch Headband
    It's Just a Phase Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Beach Glass Stretch Headband - The Sassy Olive Beach Glass Stretch Headband - The Sassy Olive
    Beach Glass Stretch Headband
    Beach Glass Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Feel the Fern Wrap Headband - The Sassy Olive Feel the Fern Wrap Headband - The Sassy Olive
    Feel the Fern Wrap Headband
    Feel the Fern Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Toasty Stretch Headband - The Sassy Olive Toasty Stretch Headband - The Sassy Olive
    Toasty Stretch Headband
    Toasty 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.