How to Sleep with Headphones and Earbuds Comfortably

How to Sleep with Headphones and Earbuds Comfortably
Written by Maisie Bygraves on Dec 27, 2021.
Scientifically fact checked by Kokoon.


How can I sleep comfortably with headphones and earbuds on?

Sleeping with headphones has often been regarded as being tricky and feeling uncomfortable, but luckily thanks to modern technology and devoted designers, it’s now a lot less finickity and a much more enjoyable experience.

Sleeping with headphones on, or earbuds in, can be different for back and side sleepers. Side sleepers often require a design that’s much more discreet, eliminating discomfort throughout the night whilst lying on their side and back sleepers often have fewer issues as their ears don’t press against their pillow. 

But whichever type of sleeper you are, we have a few tips and tricks to help you sleep with headphones and earbuds comfortably, night after night.

6 tips on how to sleep with headphones

  1. Choose the right pillow
  2. Find the best sleeping position
  3. Pick comfortable earbuds
  4. Pick comfortable headphones
  5. Go wireless
  6. Make sure you practice

1. Choose the right pillow 

Choosing the right pillow can have a positive impact on your sleep and consequently the comfort of your headphones and earbuds. If you’re a side sleeper who wears earbuds, choosing the right pillow can improve your wearing experience. 

Ensure you choose a softer pillow allowing your ears and earbuds to sink into it - relieving any unwanted pressure. This will make sure you have a comfortable night’s sleep whilst enjoying using your headphones and earbuds. 

A harder pillow can feel uncomfortable and push the buds too far into your ear, causing your sleep to be disturbed. 

When wearing headphones, you’ll find that a softer pillow may relieve any pressure caused by your headphones touching the pillow. So opt for a softie too.

2. Find the best sleeping position

As mentioned, sleeping on your side can work as long as you opt for in-ear buds, as they won’t disturb your sleep in comparison to over-ear, which are much bulkier.

Back sleepers have it a lot easier and have much more choice when it comes to headphones for sleep. But for those of us who are side sleepers, we can wear in-ear buds that are small and discreet, whilst still comfortably sleeping on our side.

3. Pick comfortable earbuds

When wearing earbuds for sleeping, choosing the right bud size can make a huge difference when it comes to sleep quality. Kokoon’s Nightbuds come with a variety of bud sizes that you can play around with and fit for size.

If you wear buds that are too big for your ears then they’ll feel more prominent in your ear, especially when pushed into a pillow when lying on your side. If the buds are too small they can feel quite invasive and uncomfortable in the ear. So, taking the time to find the perfect bud size can really pay off. 

It’s worth mentioning that the design of the earbuds is also paramount. Some earbuds are hard and unmalleable, whereas others have been meticulously designed to slot into the ear and adjust easily due to their flexible materials. Nightbuds are super flexible and soft, offering a barely-there feel.

You can find out more on the Kokoon Nightbuds page.

4. Pick comfortable headphones

When it comes to over-ear headphones, finding a comfortable pair can make a huge difference to your night’s sleep. Here are the things to look out for when researching the best headphones for sleeping

  • Breathable fabrics
  • Flexible materials 
  • Fit 


It can be trial and error when finding the perfect pair of sleep headphones. Kokoon's Nightbuds are four times thinner than the average earbud, giving you the ultimate level of comfort when sleeping - even on your side!

You can also choose from a number of different eartips to find a size that fits you.

5. Go wireless

Wearing wireless headphones and earbuds can help with potential sleep disruptions caused by the wires. Having Bluetooth instead of wires means you don’t need to be conscious of the wire when sleeping and your device doesn’t need to be close enough for the headphones to reach your head, allowing you to move freely.

6. Make sure you practice

When it comes to sleeping with headphones and earbuds, getting used to wearing them in bed should be part of the process. Starting anything new can take some getting used to, especially wearing something in your ears when you’re not used to it. 

Usually, after a few days you’ll get used to wearing them when in bed, so much so that you’ll stop noticing them altogether. And they’ll become a regular part of your nighttime routine.

The benefits of persevering and using headphones at night can be well worth it. Especially if you’ll be using them to listen to sleep audio and for relaxation. Nightbuds even monitor your sleep and show you some cool sleep insights too. So get practicing!

How do I sleep with headphones without breaking them?

When you’re sleeping, you’re not as in control of your movements as when awake. And damage to headphones can occur as a result of unexpected bedtime movements. However, having a soft pillow that can help cushion your headphones and earbuds whilst you sleep can ‘cushion’ the blow.

If you do take them off during the night, make sure you pop them onto a side table so you avoid rolling on them, or pushing them off the bed.

Our recommendation, though, is to use earbuds when sleeping. Their slim design, such as that of the Kokoon Nightbuds, fits comfortably in your ear and will not disturb you during your sleep.

What’s the best way to comfortably sleep with headphones?

  1. Choose a soft pillow to cushion the headphones. 
  2. When wearing earbuds, sleep on your side or on your back. 
  3. When wearing headphones, sleep on your back.
  4. Choose a wireless pair so the wires don’t interfere with your sleep. 
  5. Practice different sleeping positions to find out which works best for you.

How do I sleep on my side with headphones?

Some lucky folk can naturally sleep on their side with headphones. However, many of us need a little training or additional items in the bedroom to help. Start with a super-soft pillow to absorb the pressure that a hard pillow would cause. If this doesn’t help then you may want to think about opting for in-ear buds. 

In-ear buds like Kokoon’s Nightbuds are a great option if you sleep on your side, as they discreetly slot into your ears and have been designed to feel comfortable when sleeping.  

Soon, we’ll be releasing a headphone pillow to wear with your Nightbuds, so you can sleep even more soundly. Here are some of its dreamy features:

  • You can customise the height and firmness of your pillow with our removable CoolCubes. 
  • Two different sides for different temperatures. One to maximize airflow with active temperature regulation technology, the other optimized for sublime softness. 
  • 100% natural premium cotton especially optimised for softness on the skin and breathability.

Watch this space for the release of our headphone pillow and check out the Nightbuds below:

discover nightbuds

How do I keep earbuds in while sleeping?

Keeping earbuds in whilst sleeping usually depends on the fit and size of the bud. Making sure you’ve chosen the right bud fit will be the difference between your earbud staying in or falling out. 

We send out a variety of bud sizes for you to choose from, so they stay in whilst you sleep. Make sure you choose a size that isn’t too big that it doesn't fit inside your ear comfortably, or too small that it jiggles around in your ear.

Get started with headphones and earbuds specifically designed for sleep

Headphones and earbuds designed for sleep can make an immeasurable difference to your sleep, if you get the fit and environmental factors right. By following our tips in this blog on how to sleep with headphones and earbuds, you’ll not only learn how to wear them, but how to wear them comfortably. 

Start with a pair of Kokoon’s in-ear Nightbuds and see where the world of headphones and earbuds for sleep can take you!

Shop Nightbuds


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