Skip to content
  • Shop
    Shop
    • Shop by Collection
      Shop by Collection
      • Newest Arrivals
      • Best Sellers
      • Sassy Medical Collection
      • Dental Headbands
      • Detroit Football Vibes
      • Taylor Swift Inspired
      • Everything Fall
      • Holiday Headbands
      • The Michigan Mitten
      • Book Club
      • Outdoorsy Maiden
      • 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 Pattern
      Shop by Pattern
      • Floral
      • Hobbies & Obsessions
      • Naughty & Swears
      • Occupations
      • Paisley
      • Plants & Animals
      • Pride
      • Solid Colors
      • Sports
      • Tie Dye
      • Western Prints
      • Shop All Headbands
    • More
      More
      • In-Person Workshops
      • The Sassy Monthly Vibe Club
      • Gift Card
      • Scrunchie Packs
      • Grab Bags
      • Bundle Deals
      • Mommy & Me
      • Clothes
      • 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
  • My Sassy
    My Sassy
    • My Account
    • My Rewards
    • My Subscriptions
    • My Style Profile
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
    Shop by Collection
    • Newest Arrivals
    • Best Sellers
    • Sassy Medical Collection
    • Dental Headbands
    • Detroit Football Vibes
    • Taylor Swift Inspired
    • Everything Fall
    • Holiday Headbands
    • The Michigan Mitten
    • Book Club
    • Outdoorsy Maiden
    • Shop All Headbands
    Headband Styles
    • Sassy Stretch
    • Top Knot Sassy
    • Sassy Wrap
    • Sassy Twist
    • Boho Buff
    • Baby Sass
    • Shop All Headbands
    Shop by Pattern
    • Floral
    • Hobbies & Obsessions
    • Naughty & Swears
    • Occupations
    • Paisley
    • Plants & Animals
    • Pride
    • Solid Colors
    • Sports
    • Tie Dye
    • Western Prints
    • Shop All Headbands
    More
    • In-Person Workshops
    • The Sassy Monthly Vibe Club
    • Gift Card
    • Scrunchie Packs
    • Grab Bags
    • Bundle Deals
    • Mommy & Me
    • Clothes
    • 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
  • My Sassy
    • My Account
    • My Rewards
    • My Subscriptions
    • My Style Profile
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: Bestsellers

Our most-loved headbands, chosen by thousands of happy customers. Shop the bestselling styles and patterns everyone keeps coming back for — soft, comfy, and handmade in Michigan.

Headband Style Reset
Pattern Reset
Show more Show less
Color Reset
Show more Show less
Sort by

289 products
Filter and sort
Filter and sort

289 products

Headband Style
Clear
Pattern
Clear
Color
Clear
Clear
Clear all

289 products

  • Sixties Gardens Stretch Headband - The Sassy Olive Sixties Gardens Stretch Headband - The Sassy Olive
    Sixties Gardens Stretch Headband
    Sixties Gardens Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Frond of You Wrap Headband - The Sassy Olive Frond of You Wrap Headband - The Sassy Olive
    Frond of You Wrap Headband
    Frond of You Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Fuck Directly Off Stretch Headband - The Sassy Olive Fuck Directly Off Stretch Headband - The Sassy Olive
    Fuck Directly Off Stretch Headband
    Fuck Directly Off Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Cutie Mushrooms Wrap Headband - The Sassy Olive Cutie Mushrooms Wrap Headband - The Sassy Olive
    Cutie Mushrooms Wrap Headband
    Cutie Mushrooms Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Barbie& Barbie&
    Barbie's Bandana Paisley Stretch Headband
    Barbie's Bandana Paisley Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Owls Give a Hoot Stretch Headband - The Sassy Olive Owls Give a Hoot Stretch Headband - The Sassy Olive
    Owls Give a Hoot Stretch Headband
    Owls Give a Hoot Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Boho Punch Wrap Headband - The Sassy Olive Boho Punch Wrap Headband - The Sassy Olive
    Boho Punch Wrap Headband
    Boho Punch Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • The Occult Wrap Headband - The Sassy Olive The Occult Wrap Headband - The Sassy Olive
    The Occult Wrap Headband
    The Occult Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Rosa Floral Wrap Headband - The Sassy Olive Rosa Floral Wrap Headband - The Sassy Olive
    Rosa Floral Wrap Headband
    Rosa Floral Wrap Headband
    Regular price
    $18.00
    Regular price
    Sale price
    $18.00
    Add to cart
    Quick view
  • Coffee Beans Stretch Headband - The Sassy Olive Coffee Beans Stretch - The Sassy Olive
    Coffee Beans Stretch Headband
    Coffee Beans Stretch Headband
    Regular price
    $15.00
    Regular price
    Sale price
    $15.00
    Add to cart
    Quick view
  • Baby Feet Stretch Headband - The Sassy Olive Baby Feet Stretch Headband - The Sassy Olive
    Baby Feet Stretch Headband
    Baby Feet 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
  • Craft Show Schedule
  • Book a Private Party
  • 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

Be the first to know about new collections and exclusive offers, and get 10% off for signing up!

  • 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
  • Visa
Home
Menu
Search
Shop

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