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Comfortable Headbands That Don’t Pinch (Reader Favorites!)

  • Kara
  • December 18, 2020
  • Contains Affiliate Links

This year as I’ve been spending more and more time in front of Zoom calls, I’ve been trying out new ways to ~spice~ up my top half look. Statement earrings, fun bold lipsticks, that sort of thing. And when it comes to hair accessories, my new favorite go-to are headbands.

I love being able to keep my hair down all day but still have it out of my face. Plus, hair accessories are fun on camera and add a pop of personality. But hot dang, headbands can really hurt if they’re too small!!! So I asked you on Instagram to recommend super comfortable headbands and here’s the list of winners that I kept seeing over and over again (plus some of my personal favorite painless headbands!)

Comfortable Headbands That Don’t Pinch (According To Readers!)

J.Crew headband
Wallflower and Co pretzel headband

The key is finding a headband that is stretchy or bendy so it’s not pinching your temples all day. I also like to find ones that have padded ends to help cushion around my temple. Bonus points if the fabric is super soft because that makes it easier to wear all day.

I think I may just have a big head? Finding no headache headbands has always been a life long struggle for me. But I’m thrilled about finally finding – thanks to you guys, my wonderful Whimsy Soul community – some cute comfortable headbands that don’t pinch and are affordable, too! I got a LOT of suggestions on Instagram but if I couldn’t try out the headband to verify the comfiness level, I only included companies/brands that more than one person recommended.

Comfortable Headbands That Don't Pinch (Reader Favorites!)

These are the most comfortable headbands that don't pinch (according to readers!) By popular vote, these ouchless headbands are cute with no headaches after a day of wearing them. No hairbreakage, either!

Photo Credit: jcrew.com

J.Crew 

Hands-down, the most popular answer for my call on Instagram was J.Crew headbands. Readers gave such positive reviews about how J.Crew offers tons of styles available that are all made to be comfy and cute. I bought myself this pretty white knot headband with beads that instantly dresses up any outfit. I find that I can wear this all day while working with minimal discomfort.

Photo Credit: wallflowerandco.com/

Wallflower & Co

Shoutout to my friend Brianna who suggested this local Latina-owned boutique that sells a super cute headband that doesn't pinch.I know because I instantly bought myself the Jour De Bretzel headband in orange when she showed me her store!! The name translates to "Pretzel Day" which is an added fun nerdy joke from The Office. And you can feel great about supporting a small woman-owned business. It's win win win win.

Photo Credit: Anthropologie.com

Anthropologie

Another popular submission was Anthropologie. Followers love their wide array of interesting hair accessory colors and fabrics. They mostly have knotted headbands styles but also some turban headbands and a few dainty ones for more minimal styles. Most followers who suggested Anthropologie did note that they have smaller heads, so they may not be the best purchase if you have a large head (like me!)

Photo Credit: versedskin.com

Versed

Ok, you're probably like"Kara, isn't Versed a skincare company?" And yes, they totally are. BUT they sell THE most comfortable headband out there with a skincare bundle and it was this headband that actually started my obsession with wearing them in the first place. It's super soft and squishy, doesn't pinch my head at all and even machine washable (if you happen to sweat a lot while wearing it.)

After sporting this headband for like, a month straight, I finally decided I needed to shop other styles and thus was born my hunt for the best headbands for big-headed people like moi.

Photo Credit: loft.com

LOFT

A few readers suggested loft (and they had a great black Friday sale) so I snapped up a headband from them as well. Happy to confirm that my blush knotted headband is super bendy and doesn't pinch my head at all! I actually usually forget that I'm wearing it when I do, and that's honestly all that I could ask for. They don't have any many styles at Anthro has but they do offer some really great staple pieces you can wear with pretty much anything.

Photo Credit: walmart.com

Wild Primrose x Scunci 

You probably know the Scunci name from those comfortable fabric headbands that look like they were pulled out of the 80's. But this is 2020. A few readers suggested the Wild Primrose x Scunci collab (at Walmart) for affordable yet comfy slide on headbands that - dare I say it - look like they were maybe inspired by Anthropologie. But they're all under $10!

Kara

I'm the founder of Whimsy Soul (this blog you're reading!) I'm a type 3 enneagram cat lady who lives in San Francisco and loves to find everyday magic to share with others. You can probably find me hunting down hot springs with girlfriends, kayaking, cooking with my husband, petting strangers' dogs or watching like, all the things on Netflix. Follow me on Instagram for even more inspiration!

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