Simple Tips to Sleep With Headphones & Get Your Best Ever Rest

There’s plenty of reasons to wear headphones while getting to sleep, but it can be tricky to get it right.

There’s no point listening to a sleepcast if you get woken up later by headphones poking into you while you sleep.

In this article, I’ve put together all the tips and tricks I’ve found to sleep with headphones on. Including:

  • Why headphones can give you a better sleep
  • Changing your position to accommodate headphones
  • The best ‘sleep phone’ recommendations
  • Ways you can sleep on your side with full-sized headphones on.

Sound good? Then let’s dive right in.

Benefits of Sleeping With Headphones

First off, I want to cover the huge claim I put in the title. So before we get into the ‘how’, let’s cover the ‘why’ you should try sleeping with headphones on.

  1. Immunity from noise. Lots of people sleep with headphones because they’re in a noisy apartment. Believe my, I’ve been there. Police sirens, kids screaming, music blaring, cars honking. Not exactly a blissful paradise. Noise cancelling ear plugs CAN work, but you can often still hear these noises. Instead, playing soothing music or listening to someone’s voice can completely fade out those outside distractions.
  2. Better sleep. It’s proven that white noise can help improve the quality of sleep. Listening to it through headphones can be a great balance if it helps you, but not your partner.
  3. Enjoy ASMR. Standing for autonomous sensory meridian response, ASMR is defined as: “a feeling of well-being combined with a tingling sensation in the scalp and down the back of the neck, as experienced by some people in response to a specific gentle stimulus, often a particular sound”. Listening to an ASMR track can help you relax, and in turn, enjoy a better and more restful night’s sleep.
  4. ‘Learn’ while you sleep. There’s a select few people who swear by sleep learning. That is, revising something as you sleep and still listening to it as you drift off. Results may vary, but it could help accelerate that language you’ve been hoping to learn.

1: Train Yourself to be a Back Sleeper

Before we start with tips that involve other ‘things’, I want to explore the quickest cheapest option. One that doesn’t need any new special equipment. And that’s changing your sleeping position.

When it comes to sleeping with headphones, back sleepers have it so easy.

They can pop headphones on, lay back and relax – not even thinking twice about it. They’d probably be shocked that a post like this even exists!

We have a whole guide on training yourself to sleep in a different position here.

2: Consider Sleep-Friendly Headphones

Sleeping with normal headphones isn’t possible for side-sleepers. The earpiece pushes into us, building up pain and making our ear super sensitive. The music gets distorted, and we even risk breaking the earpiece! 

Using sleep-friendly headphones is the simplest and quickest solution to this problem. 

But as the Cheap, Fast, Easy triangle goes – we can only have two options: fast and easy. So this solution might cost a bit of cash.

(That said, since sleep is so fundamental to our health, alertness, emotions, happiness, diet, willpower, etc… I’d argue that it’s worth a small investment to get a better night’s sleep!)

Now, one quick comment. This applies to all the options below: Make sure your headphones fit correctly!

There’s nothing more annoying than earbuds which fall out or headsets that slip off. Take the 10 minutes to test the different sizes of earbuds that you get or adjust your headset band. You want things to fit firmly and snugly. This will massively reduce the chance of getting frustrating during the night.

Ok, disclaimer done. Moving on – there’s two main options here:

  1. Super Small EarBuds
  2. A Sleep ‘Band’.

Let’s look at both, and then I’ll comment on tips for standard headphones.

Sleep EarBuds

The ear buds are so small you can even lay on your side and not apply pressure to them. They fit inside your ear. So small, that they don’t even get pressure put on them if you’re resting your head on your side. The other major benefit is that they’re often noise cancelling.

These products are still a developing technology – but the best model so far are the ZenBuds by Amazfit.

They’re tiny enough to fit snugly inside your ear, while staying comfortable and allowing you to sleep on your side. Though their price tag isn’t cheap, I wouldn’t hesitate in saying they are the best solution for anyone wanting a peaceful sleep with headphones in.

Sleep Bands

Onto the sleep ‘band’. I personally love these, though they’re not the best in all situations. It’s like wearing a comfy headband to bed – it almost just feels like part of your pajamas. Subtly there’s a headphones woven into the side – just strong enough to let you listen to music or a sleep cast.

These are great as an easy solution, though their major downside is a lack of noise canceling (compared to the earbuds).

One suggestion is these Sleep Headphones sold on Amazon.

It’s the same generic brand sold by many different manufacturers – they provide a great balance of comfort, audio quality, and long-lasting battery life.

Standard Headphones

Although those first two options are ideal for sleeping, I do need to make one further comment.

If you’re not into either option, I’d recommend at least choosing wireless headphones instead of wired. For the simple reason that there’s no cord that might wrap around your neck and give you an unpleasant awakening!

Of course, wireless have their own issue: battery levels. The best way to solve this is to have the charger by your head, and use one set of headphones dedicated for sleep. This way it becomes a habit to put them on charge when you wake up.

If you absolutely must use a wired set, keep the source of the wire above your head. In other words, at the top of your bed, by the the headboard. This way, any tossing and turning may only twist the wire, and you won’t wake up with it around your neck or in your face.

3: The Infamous PWAH.

Don’t worry, I don’t mean getting yourself knocked out by a punch so strong it goes PWAH!

It stands for Pillow With A Hole. A special product designed to leave space around your ear.

Normally this is used for those with ear issues, or after ear surgery. But hey, it also happens to be perfect for sleeping with headphones!

The pillow itself is fairly simple. As you can see, there’s a massive hole in it.

[PIC #]

Since it’s so specialist, it’s very customisable. You can add or remove the material in it to change it’s firmness, or even replace the inside altogether. You can also change the padding around the hole to widen/tighten it to your liking.

It’s a simple but ingenious solution to our problem. That said, it’s not without it’s issues.

Honestly, it’s not the most comfortable thing in the world. It works – don’t get me wrong. But it’s not the same level of comfort as placing your whole head on a comfy pillow. It’s something you need to get used to.

The other downside is if you move in the night. In the dark it can be hard to line up your headphone piece with the hole (and that’s if your conscious). You may just find yourself half away, fighting this weird reverse donut thing and wishing for a good pillow instead!

For the actual ‘sleeping with headphone’ part, though, it’s pretty unbeatable. It works super well and you can drift off without an ounce of pressure being put on your headset.

Note: This doesn’t really work with larger headsets or those with rigid headbands. Super large earpieces don’t quite fit into the hole. Rigid headbands still push off the edges of the hole, putting pressure onto your head.

4. Working with Travel Pillows

You know travel pillows, right?

These things:

[PIC #]

Turns out they’re a pretty quick replacement for our PWAH friend above!

By turning one so that the thick bottom part is at your chin, and the opening is at your head, you’ve suddenly got your own DIY PWAH! Complete with a space for the headband to sit at the top. Perfect.

Obviously, this is not a pillow made to last a whole night’s sleep. But it can be a fantastic temporary solution. Use it to listen to music or a sleep cast and take the headphones off before you sleep. Simple. You could use it throughout the whole night if you were able to stick to one sleeping position, but it’s not exactly The Ritz of bedtime sleeping setups.

Still, it’s a great little ‘hack’. For anyone interesting in the Pillow Without A Hole, maybe give this one a shot first. See how you find it.


Sleep is one of the most important parts about being healthy and happy.

Having it disturbed from outside noises, a snoring partner, or even just a wandering mind can make the rest of our life a lot more challenging.

Being able to block out noise and listen to your favorite relaxing music or sleepcasts can change everything. I hope this quick guide has helped give you a few ideas on how to use headphones to massively improve your sleep quality.

If you liked this article, please consider checking out our related posts below!

Thanks for reading, and I hope you sleep well.


Helping you get the best night of sleep possible. Sharing what I learn through my research and testing.

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