Best answer: Yes, but as with anything, just because you can do it doesn't mean you should do it. You'll have to rule out on-ear and over-ear headphones, but in-ear headphones shouldn't be a problem.
Comparing different headphone styles
First and foremost, let's explore the different headphone types: on-ear, over-ear, and in-ear. If you sleep on your side, over-ear and in-ear are off the table since you'd be physically lying on the headphones themselves. However, if you lie down facing the ceiling, you could possibly make it work, but only if you know that you don't toss and turn while you're sleeping. Using on-ear or over-ear headphones is definitely not recommended.
What we recommend is using a set of in-ear headphones since those typically don't have anything sticking out of your ear or resting on your head. Generally speaking, you should go for "truly wireless" headphones that don't have a cable going from one bud to the other. Even with in-ear earbuds, there's no guarantee that they'll stay in your ears all night.
Why you shouldn't wear headphones while sleeping
If you plan on playing fast-paced music such as most pop, rock, or hip hop music, sleeping with headphones on isn't ideal. Those genres of music tend to keep people moving, dancing, and awake. This also applies if you're planning to use your headphones at higher-than-usual volumes.
Ideally, you'll want to use headphones while sleeping to either completely block out the outside world, play audiobooks, podcasts, or more soothing music such as jazz or classical. You'll probably want to set a sleep timer on your phone or computer as well, so audio isn't pumping all night and draining your headphone's battery.
Like we mentioned earlier in the post, over-ear and on-ear headphones aren't recommended solely because the headband will make it nearly impossible to sleep. We also don't recommend wired headphones since they can become incredibly tangled while you're sleeping, on your device, or around your neck, and pose a hazard.
Choosing the right in-ear headphone
There are two things that make great headphones: comfort and sound. If you compromise on either, you'll have a really tough time with any set of headphones at any time of day.
Let's take a look at what your options look like. The just announced Galaxy Buds are great if you're looking to enter the headphone market for the first time. Not only are they good for sleeping, but they're a solid choice for your first real headphone purchase.
They stay in your ear with the wings and ear tips and have a solid sound signature that is neutral. The charging case allows for up to one full charge and charges through USB-C or wirelessly through the Qi standard.
If you have a slightly larger audio budget, the Sennheiser Momentum Truly Wireless is a great set if you want to really step up your audio game and have excellent wireless audio quality and fidelity. From personal experience, these stay comfortably in your ears. The audio quality is great with a small emphasis in the treble region. The bass and mids/mid-range are neutral and natural sounding and don't get muddy in any way.
Works great with the latest Samsung devices
These are the definition of truly wireless, with individual left and right earbuds and a portable charging case that charges wirelessly on any Qi-compatible charging pad.
Asleep or awake, these won't disappoint
These headphones offer great sound without any extra features. They're pricey but are great all-around earbuds that offer exceptional sound and are definitely worth the money.
Maybe try speakers?
If headphones aren't your thing, looking for a solid speaker may be your best option. With speakers you don't need to worry about the headphone type, nor do you have to worry about comfort.
With a speaker, you'd be looking at size and volume, in addition to sound and price. This is why we recommend the Ultimate Ears Wonderboom. It's a relatively small speaker that packs some serious punch in the low end.
While we're recommending it as a bedside speaker, it's a solid all-around speaker as well. Not to mention it's waterproof. The Wonderboom offers a 10-hour battery life, which is fine for most while sleeping. You can optionally plug it in while using it as well to extend usage if need be.
While bringing a speaker along isn't always the ideal situation, for the most part, you can just use a speaker of any kind to get your nighttime audio. With a dedicated speaker, you don't have to worry about battery life (generally plugged in) or the headphones falling out of your ears. Happy sleeping!
A great all arounder
Removes the worry about comfort and fit. Waterproof, and long battery life.
The Wonderboom is designed for the modern world, and is relatively cheap but packs a great sound. It also sports an IPX7 water resistance rating and a 10-hour battery life, which means you can get through the night without an issue.
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