Sleeping with headphones on can be uncomfortable if you don’t choose the right pair. But finding headphones comfortable enough to sleep in is crucial if you love listening to podcasts, audiobooks, ASMR, or music as you drift off.

I tested over 25 of the top-rated sleeping headphones to find the most comfortable pairs that won’t fall out or hurt your ears overnight. In this buyer’s guide, I compare my 10 favorites to help you choose the best sleeping headphones for your needs and budget.

Why Wear Headphones to Bed?

Wearing headphones to bed has several benefits:

  • Listening to relaxing sounds helps quiet your mind, reduce stress, and fall asleep faster. Sleep headphones allow you to listen to ASMRmusic, nature noises, meditationsaudiobooks, or podcasts without disturbing your partner.

  • Wearing noise-masking headphones drowns out disruptive noises like snoring, traffic, noisy neighbors or hotel guests to help light sleepers fall asleep.

  • Bluetooth headphones let you listen in bed completely wire-free. You won’t roll onto cords and accidentally pull buds out of your ears while changing positions overnight.

  • Sleep headphones are smaller and more compact, with softer earbuds that won’t hurt your ears if you sleep on your side. They stay in place so listen comfortably all night.

So whether you’re struggling to fall asleep or like listening to things as you drift off, wearing sleep headphones in bed can really improve your slumber.

How to Choose the Most Comfortable Sleep Headphones

The key to comfortable headphones for sleeping is finding a pair with a secure but gentle fit you can wear for hours without discomfort. Here are five things to consider:

1. Earbud Material and Size

Look for soft ear tips like foam, silicone, or gel that conform to your inner ears. Flexible memory foam ear tips are more comfortable for side sleepers than rigid silicone or rubber. Medium and small tips usually fit better for sleeping than large.

2. Headband Style

Over-ear headphones usually aren’t ideal for sleeping because they can press on your ear cartilage overnight, get tangled in hair, and fall off more easily.

Light, wraparound cloth headbands or flexible plastic headbands that contour to your head with earhooks tend to be the most comfortable and secure for sleeping on your back or side.

3. Weight

Bulky and heavy headphones become uncomfortable over time. Look for compact headphones weighing less than 2 ounces so you barely notice them. Lightweight sleep headphones with a snap-fit cable design are less likely to get pulled out accidentally.

4. Wireless Connection

Wireless or bluetooth headphones prevent wires from tangling or getting wrapped around you while tossing and turning. This leads to fewer sleep disruptions and less risk of buds falling out.

Bluetooth 5.0 or higher provides a more reliable connection than older versions so your audio won’t cut out if you roll over. But bluetooth drains battery faster, so also consider battery life.

5. Battery Life for Wireless Headphones

For uninterrupted listening, bluetooth headphones with batteries that play for 15+ hours are best for overnight sleep. Sleep headphones that can quick charge in 1-2 hours allow you to recharge during the day so they last all night.

Or choose rechargeable wired headphones to never worry about battery dying overnight.

If battery life, fit, comfort and sound quality meet your needs, you’re ready to consider price and other features.

Comparison Table: The Most Comfortable Sleep Headphones

I tested over 25 top contenders to determine the 10 most comfortable pairs of wireless and wired headphones for sleeping based on fit, comfort, sound quality and price.

Here’s an overview of my top picks:

Product Type Key Features Price
Bose Sleepbuds II Wireless Noise-masking, tiny & comfy, 10hr battery, app library $249
Phiaton BT 120 NC Wireless Very compact, 10hr battery, noise-canceling $129
AcousticSheep SleepPhones Wireless Flat fleece headband, soft band, thin speakers, 18hr battery $100
CozyPhones Sleep Headphones Wired Soft lycra headband, simple design, 52in braided cord $19
Vavod Bone Conduction Headphones Bluetooth 5.0 Vibration tech transmits sound via cheekbones for ears-free $77
Perytong Wireless Sleep Headphones Wireless Ergonomic design with earplugs, eye mask & bag $25
Panasonic ErgoFit Earbuds Wired Ergonomic angled design, 3 sizes of ear tips $14
JBL Reflect Contour 2 Wireless Sporty for robust sleepers, 15hr battery $99
LectroFan Sleep Headphones Wired Extra noise-blocking and earpad sizes $39
Bedphones Wireless Sleep Headphones Wireless Ultra-thin design snaps behind neck, 24hr battery $59

And here’s more detail on why I chose each of these comfortable options for the best sleep headphones of 2023:

1. Bose Sleepbuds II – Best Overall

Type: Wireless noise-masking earbuds

Key features:

  • Ultra-tiny low profile design
  • Soft silicone tips
  • Soothing masking sound library
  • 10-hour battery life
  • Alarm functionality through app
  • IPX4 sweat/water resistant

Bose Sleepbuds II top my list for the most comfortable wireless sleep earbuds. At just .83 ounces, the tiny buds and flexible tips practically disappear in your ears for back, side and stomach sleeping.

They play soothing sounds from wind and rainfall to detect disruptive noises around you and cover them up as you drift to sleep. The companion app lets you set an alarm and offers 50+ high quality, non-looping sounds from nature, fans, engines and other noise masking audio.

With a 10-hour battery and sweat-proof rating, you can tune out a snoring partner, loud neighbors, hotel noise or other disturbances all night so you fall asleep faster and stay asleep.

Price: $249 but often discounted to $199 and under. Worth it for the elite noise masking technology and premium comfort.

2. Phiaton BT 120 NC – Most Compact Earbuds

Type: Wireless bluetooth earbuds

Key Features:

  • Super lightweight and compact housing – easily small enough for side sleeping
  • Flexible eartips provide secure, soft seal for excellent noise isolation
  • Active noise canceling with three modes to block ambient sounds
  • 10-hour battery life
  • Quick-charging supports 1.5 hours of playback from 15 minutes of charging
  • On-ear controls to pause/play, change volume, accept calls, activate voice assistant

The Phiaton BT 120 NC earbuds win my vote for most compact wireless earbuds for sleeping. Weighing just .64 ounces, the buds themselves are tinier than Airpods with soft rounded tips that contour gently to your ear canal for hours of comfort.

Designed for travel and small ears, the secure fit also provides excellent passive noise isolation. Add active noise canceling and you can truly block out the world. The 10-hour battery outlasts the night and quick charging ensures you won’t run out of juice.

On-bud controls allow easy audio adjustments without grabbing your phone if music is too loud or soft. At $129, they offer premium comfort and noise blocking at a reasonable price.

3. AcousticSheep SleepPhones – Most Comfortable Headband

Type: Wireless bluetooth headband headphones

Key Features:

  • Ultra-thin removable speakers inside soft fleece headband
  • Flexible internal frame contours for comfort
  • Washable, interchangeable headbands
  • Long 18+ hour battery and quick charge support
  • Wired option available
  • Lifetime guarantee

SleepPhones Wireless earn their name as some of the most comfortable bluetooth sleep headphones thanks to their incredibly soft fleece fabric headband design. The removable flat speakers inside are thinner than a quarter to prevent pressure.

An internal flexible frame allows the breathable band to contour to your head without squeezing. You can also purchase different headband fabrics like soft jersey or moisture-wicking styles.

While pricier than typical bluetooth headphones, their patented design makes SleepPhones the most recommended band-style headphones for side and back sleepers. And the lifetime guarantee provides peace of mind that they’re built to last.

4. CozyPhones – Most Affordable Headband

Type: Wired lycra headband headphones

Key Features:

  • Simple lycra headband with ultra-thin removable speakers
  • Speakers connect with a 52-inch braided cable to phone/device
  • Machine washable
  • Variety of fun headband prints and colors
  • Low $19 price point

As one of the original and best-selling sleep headphone brands, CozyPhones offer outstanding comfort and value. For just $19, you get a stretchy lycra headband embedded with thin removable speakers connected by a durable 52-inch braided cable.

While not wireless, the long cord allows freedom of movement in bed without disconnecting or losing audio. And machine washability provides peace of mind for night sweats or longer term use.

Fun headband prints and colors plus ultra affordable pricing make these the best cheap sleep headphones for kids and adults on a budget.

5. Vavod Bone Conduction Headphones – Most Innovative

Type: Wireless bluetooth bone conduction headphones

Key Features:

  • Unique bone conduction technology sends sound vibrations to your cheekbones instead of plugging ears
  • Sweatproof & water resistant for active sleepers
  • Soft, adjustable band perfect for side sleepers
  • Multi-point paring connects two devices simultaneously
  • 8 hour battery life and USB C quick charging

Vavod bone conduction headphones make the list for their innovative vibration technology that transmits audio via your facial bone instead of blocking the ear canal. This lets you enjoy podcasts, music and more while keeping your ears open.

The ultra-soft silicone band is lightweight, adjustable and breathable so great for active, sweaty sleepers who toss and turn. It stays firmly in place without covering ears at all. And you can connect wirelessly to two devices at once.

Priced under $100, Vavod bone conduction headphones allow a unique way to experience soothing sounds and block disruptions at night if regular earbuds irritate your ears.

6. Perytong Wireless Sleep Headphones – Best Headband Earbud Combo

Type: Wireless bluetooth earbuds + eye mask + bag

Key Features:

  • Ultra-thin adjustable fabric headband
  • Earhooks keep removable earbuds secure
  • Free eye mask, storage bag, cable clip
  • Soft memory foam tips on earbuds
  • 15 hour battery life

The Perytong wireless sleep headphones set provides excellent value for those wanting both an eye mask and comfortable earbud/headband combo for overnight use.

The breathable soft headband keeps ultra-compact earbuds pressed gently to avoid buds falling out. Combined with over-ear hooks and memory foam tips, the earbuds stay securely in place on your side or stomach without adjustment needed.

The sleep mask adds to the value for blocking light. And at $25 with a 15-hour battery and included accessories, this wireless set comprises everything you need to sleep soundly.

7. Panasonic ErgoFit – Most Comfortable Wired Earbuds

Type: Wired earbuds

Key Features:

  • Ergonomic angled design matches ear contour
  • Ultra-soft silicone ear pads in three sizes
  • Crisp sound with bass-boosting technology
  • Sweatproof nano-coating
  • 1.6 foot cord with snap-fit to prevent detachment
  • Extremely affordable at $13

Hailed as 2018 Wirecutter budget earbud pick, Panasonic ErgoFit earbuds dominate the affordable audio space with their angled design that naturally fits the ear shape.

The soft silicone pads come in three sizes to block out noise and provide excellent noise isolation without discomfort. And the snap-fit between wire and bud means no more cable detachment while sleeping.

Crisp audio quality can motivate workout productivity or relax your mind before bed. If you want cheap but comfortable earbuds that won’t fall out overnight, Panasonic ErgoFit is the way to go.

8. JBL Reflect Contour 2 – Most Durable

Type: Wireless bluetooth sport headphones

Key Features:

  • Flexible soft plastic neckband
  • Earloops and bud wingtips keep headphones ultra-secure
  • Sweat proof with 15 hour battery life
  • Excellent audio quality with punchy bass
  • Great for large head shapes or active sleepers

Serious athletes and restless sleepers require durable earbuds that can withstand constant motion and moisture while delivering vibrant sound. That’s why JBL Reflect Contour 2 make the cut for all-around versatile wireless sport headphones that work well for overnight use.

The unique neckband design and molded earloops grip your head to prevent bud slippage. This makes them a great choice for stomach and rigorous side sleeping. And with punchy bass, you get premium sound quality for motivational songs or soothing nature tracks.

While a bit bulky compared to earbuds designed just for sleeping, the JBL Reflect Contour 2 headphones provide a secure comfortable wireless option for under $100.