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The Sassy OliveThe Sassy Olive

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It’s Prime Time for Headbands

Grab bags, twist headbands, Christmas in July, all on sale now!

Shop the Sale

Twist, Shout, Save Big

  • Watermelon Twist Headband - The Sassy Olive
    Watermelon Twist Headband
    Watermelon Twist Headband
    Regular price
    $12.00
    Regular price
    $18.00
    Sale price
    $12.00
    Add to cart
    –33%
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  • Medici Floral Twist Headband - The Sassy Olive
    Medici Floral Twist Headband
    Medici Floral Twist Headband
    Regular price
    $12.00
    Regular price
    $18.00
    Sale price
    $12.00
    Add to cart
    –33%
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  • Daphne Twist Headband - The Sassy Olive
    Daphne Twist Headband
    Daphne Twist Headband
    Regular price
    $12.00
    Regular price
    $18.00
    Sale price
    $12.00
    Add to cart
    –33%
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  • Black Ivory Checker Twist Headband - The Sassy Olive
    Black Ivory Checker Twist Headband
    Black Ivory Checker Twist Headband
    Regular price
    $12.00
    Regular price
    $18.00
    Sale price
    $12.00
    Add to cart
    –33%
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Flash Sale, Full Sass

  • Generic Mystery Grab Bag - The Sassy Olive
    Generic Mystery Grab Bag
    Generic Mystery Grab Bag
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Add to cart
    –33%
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  • Medical Grab Bag - The Sassy Olive
    Medical Grab Bag
    Medical Grab Bag
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Add to cart
    –33%
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  • Scrunchie Grab Bag - The Sassy Olive
    Scrunchie Grab Bag
    Scrunchie Grab Bag
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Add to cart
    –33%
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  • Western Grab Bag - The Sassy Olive
    Western Grab Bag
    Western Grab Bag
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Add to cart
    –33%
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Holiday Sass, Prime Prices

  • Xmas Camping Stretch Headband - The Sassy Olive
    Xmas Camping Stretch Headband
    Xmas Camping Stretch Headband
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Add to cart
    –33%
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  • Unwrapped Stretch Headband - The Sassy Olive
    Unwrapped Stretch Headband
    Unwrapped Stretch Headband
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Add to cart
    –33%
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  • Tangled Lights Stretch Headband - The Sassy Olive
    Tangled Lights Stretch Headband
    Tangled Lights Stretch Headband
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Add to cart
    –33%
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  • T - rexmas Cookies Stretch Headband - The Sassy Olive
    T-rexmas Cookies Stretch Headband
    T-rexmas Cookies Stretch Headband
    Regular price
    $10.00
    Regular price
    $15.00
    Sale price
    $10.00
    Sold out
    Quick view
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Shop by Headband Style

  • Sassy Stretch Headband – The Ultimate Fit for Every Style

  • Top Knot Headbands – The Perfect Fit, Every Time

  • Sassy Twist Headbands – Stylish, Layered & Versatile

  • Sassy Wrap Headbands – Endless Ways to Wear It, One Headband to Love

  • Boho Buff-From headband to neck gaiter—style it your way.

  • Big Baby Grab Bag (Infant & Baby) - The Sassy Olive

    Baby Sass – Soft, Stylish Headbands for Babies

Shop by Pattern

  • Solids - The Sassy Olive

    Solids

  • Sporty Sass - The Sassy Olive

    Sporty

  • Floral - The Sassy Olive

    Floral

  • Medical - The Sassy Olive

    Medical

  • Boho - The Sassy Olive

    Boho

  • Western Prints - The Sassy Olive

    Western Prints

  • Tie Dye - The Sassy Olive

    Tie Dye

  • Retro - The Sassy Olive

    Retro

  • Paisley - The Sassy Olive

    Paisley

  • Spooky - The Sassy Olive

    Spooky

  • Nature - The Sassy Olive

    Nature

  • Y2K - The Sassy Olive

    Y2K

Style Your Look: Headbands for Everyone 

Short hair, long hair, curly, straight—or even no hair at all! Our headbands look amazing on everyone, including guys, girls, and kiddos. Check out easy styling tips, videos, and tutorials to find your perfect look. Because everyone deserves to feel confident rocking a headband.

Visit our Styling Blog

Behind the Seams

  • Pride in Small Places: Celebrating Visibility and Community in Allegan, Michigan - The Sassy Olive

    Pride in Small Places: Celebrating Visibility and Community in Allegan, Michigan

    May 17, 2025

    At The Sassy Olive, Pride Month is more than just a celebration—it’s a reflection of our commitment to inclusivity, visibility, and community support.In 2020, our founder, Landria Johnson, became the...

    Read more
  • The Sassy Olive’s Mother’s Day Gift Guide: Handmade Headbands for Every Mom - The Sassy Olive

    The Sassy Olive’s Mother’s Day Gift Guide: Handmade Headbands for Every Mom

    May 07, 2025

    Mother’s Day is just around the corner, and if you’re still searching for the perfect gift — don’t panic. Whether you’re shopping for your mom, your bonus mom, your plant-loving...

    Read more
  • The Canary Tales: Lack Studios x The Sassy Olive - The Sassy Olive

    The Canary Tales: Lack Studios x The Sassy Olive

    April 16, 2025

    A collaboration between Vivianne’s whimsical pattern design and The Sassy Olive’s handmade headband expertise. From her sketchpad to your head—these prints, inspired by her travels through the Canary Islands and...

    Read more
View all

At The Sassy Olive, every headband starts with imagination and ends with handcrafted perfection. Unlike others, we handle everything in-house—from designing our own vibrant patterns and printing our own fabrics, to hand-sewing every piece right here in Allegan, Michigan.

We’re proud to be original, inclusive, and a little extra—because why blend in when you were born to stand out?

Visit Us in Allegan

125 Locust Street
Allegan, MI 49010

Mon - Sat, 10:00am - 6:00pm
Sunday, 10:00am - 3:00pm

(269) 512-7117

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