The Most Comfortable Headphones for the Holidays: Over-Ear Headsets and Earbuds Under $100

Jean Bentley
·18 min read

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Just because a pair of headphones comes equipped with all the latest technology doesn’t mean they’re necessarily the best — there are two important characteristics that ultimately determine their worth. First, it’s essential that they sound good (you know, to make sure you’re successful with that whole “listening” thing you’re trying to do). But second, and almost as important, is the matter of comfort.

If you’re going to be wearing headphones all day while Zooming with coworkers or chatting with friends and family — or working with professional sound mixing equipment — you’re going to want to make sure that said headphones don’t squeeze your head too tightly or fall off or do anything else to cause discomfort.

In the spirit of the holiday season, we’ve put together a list of the most comfortable headphones you can purchase both for your work from home life, but also for an easy, useful holiday gift that most people would be thrilled to receive. We’ve included over-ear, earbud, wired, and Bluetooth-friendly options for anyone who’s searching for comfort in addition to high sound quality. The below selection is what we found when scouring user ratings and feedback, and comes complete with actual user comments regarding each pair’s fit. (And while most are Bluetooth-enabled, you can pick up an iPhone dongle here for the wired pairs that are not. This dongle also acts as a splitter so you can charge your phone and listen to music with a pair of wired headphones.)

AUKEY EP-T21 Wireless Earbuds

Listed at $49.99 but consistently available on sale for less than half that price, these Bluetooth 5 headphones feature faster pairing, crisp audio, and one-step connection to your phone (after the first time, of course). Manage audio playback and calls with the touch panel and microphone on each earbud, and use as a pair or alone (like a Bluetooth headset). You’ll get five hours of playback on one charge, and the charging case will provide an additional six charges for a total of 35 hours of playtime. The earbuds come with charging case, micro-USB cable, and three pairs of ear tips.

Wrote Amazon user Jordan Grelewicz, “I bought real AirPods when they first came out, but I didn’t like how they fit in my ear. I don’t know if my ears are too small, or I was trying to push them in too far, but they were just never comfortable for me. These fit snugly and securely, they don’t feel like they’re going to fall out, and I love the black color over the white. I sold my AirPods to a family member, but I’m definitely going to be keeping these ones.”

Apple AirPods (Wired Charging)

Held off on buying AirPods because of the price? Save $30 off the list price of the basic Apple AirPods with a wired charging case. If you want wireless charging you’ll be better off with the upgraded option (also on sale!). This model comes with up to five hours of listening time with one charge, and up to 24 hours with the charging case.

Wrote user Chris Wadden, “These earbuds have been fantastic so far. People criticize the price, but I’m sorry, there is a reason for it. I never tried the previous version, but these ones connect to my iPhone, iPad, and bluetooth transceiver almost instantly. They are very comfortable and stay in my ears with no issues. I’ve tried cheaper bluetooth earbuds, in the 50$ range, and the difference was night and day. I would pay the extra 100$ on these every day for the increase of build quality and performance.”

OneOdio Pro-10 Foldable Over Ear Headphones with Mic

This basic model from OneOdio features soft ear-cushioning earmuffs on their 90° swiveling earcups, and comes with dynamic bass sound perfect for doing, mastering, monitoring, mixing, broadcasting, tracking, and personal listening. They’re flexible, making them comfortable even for long working sessions. The headphones come with two different cables — a 6.35 to 3.5 9.8ft coiled cable and a 3.5 to 3.5 3ft cable with answer/end button & in-line microphone for hands-free phone calling — and are compatible with with professional mixers, instruments, as well as smartphones and computers.

Wrote user Sean, who uses them daily to block out noise in his cubicle, “I wear these sometimes 8 hours a day 5 days a week and the build quality and comfort you get, for the price, is second to none.”

And user Audaxia wrote, “these are very comfortable headphones, on the first day I wore them for about 5 hours before my ears started to hurt a bit but the next day I adjusted the size of the sides and it was very comfortable. I was able to wear them all day without discomfort.”

OneOdio Pro-30 Foldable Over Ear Headphones with Mic

These over-ear headphones are the next model up from the Pro-10s, and feature foldable, high-quality, memory foam-padded ear cushions specifically designed for both comfort and noise isolation, and have an adjustable and stretchable headband to make the fit even more custom. The 90° swiveling earcups allow for easy single-ear monitoring. They also come with two different cables, the 6.35 to 3.5 9.8ft coiled cable and 3.5 to 3.5 3ft cable with mic, and are compatible with with professional mixers, instruments, and everyday devices. While comfort is the main criteria here, these leather and metal headphones are also pretty stylish, too (and are Amazon’s Choice for “retro headphones”).

User Chunky Bacon! praised both the sound quality and the comfort, writing, “These actually fit all the way over my ears, unlike many other brands which tend to squish them,” as did user nonya biz, who wrote, “They are a bit bulky but really light weight, I almost forget I’m wearing them. I’ve had them for 2 days now and have wore and used almost constantly and have yet to have ears hot or sweating or any other discomfort.”

COWIN SE7 Active Noise Cancelling Headphones Bluetooth Headphones

These headphones use Active Noise Cancelling (ANC) technology to quell airplane cabin noise, city traffic, or a busy office. Although the come with an audio cable, they’re also equipped with Bluetooth and can work wirelessly as well. The built-in mic allows for hands-free calls, and the ears are covered with protein ear pads and a foldable headband making them both comfortable, flexible, and easy to transport. The battery allows for 30 hours of playtime using just Bluetooth, and 20 using Bluetooth with ANC. (And yes, certain colors slightly exceed our $100 price limit, but they’re worth including regardless.)

User Jay praised their light weight and easy portability, plus noted their comfort, writing, “The pads are nice and soft and do not hurt the ears after hours of use. They are also detachable so they can be replaced if needed.”

COWIN E7 Active Noise Cancelling Bluetooth Headphones with Microphone

This slightly more basic model of the COWIN Bluetooth headphones comes at a cheaper price point, but with similar features. They come in fun rainbow colors (red, yellow, green, blue, purple, white, and black) with silver accents, and a whopping 43,109 ratings give this pair of headphones an average score of 4.4 out of 5, meaning the positive feedback isn’t boosted by bots.

User Lucas Jon praised their comfort, but warned that they’re better suited to lower-intensity activity. “These sit very comfortably on my head while I do chores around the house or yard work etc. I run a mobile auto detailing business in my spare time and use them for that as well. I don’t have a particularly large head and they fit nicely, but I imagine they would be better for someone with a big noggin. If I find myself looking down for too long they will start to slip off my head,” he wrote. “I wouldn’t even attempt to do any kind of cardio with these. Weightlifting, sure but running – no.”

Status Audio BT One Wireless On-Ear Headphones

These modern, minimalist headphones come with a padded adjustable headband in addition to cushy folding earcups for maximum comfort. The lightweight design also includes a microphone and volume and playback controls with Bluetooth 5.0 technology that allows you to connect two devices at the same time with no lag, even when switching between devices. A 30-hour battery can be fully recharged in just over an hour via USB-C with Qualcomm’s QuickCharge technology.

According to user Sam O., the sound quality is the biggest selling point but “In terms of the feel and comfort of the headphones, they do a much better job than other over-the-ear headphones I’ve owned before. I have a big head and, despite that, these headphones adjust very well to my head. The material of the headphones is definitely comfortable and I can keep them on for long periods of time with no real problem.”

And user Lane S. wrote, “I use them professionally in film and television. I needed a good BT set for location filming that didn’t cover my entire ear and make it cumbersome to slip off and put around my neck constantly. Over ears are too big to comfortably do this so you end up putting on the top of your head and look like an idiot. Or take off and have to keep looking for them.”

Mpow H7 Bluetooth Headphones

Another pair of sleek, brightly colored Bluetooth over-ear headphones, these offer up to 25 hours of rechargeable battery life and a 3.5mm audio cable changes the wireless to wired mode to keep listening when the battery runs out. The three-button easy control allows you to operate audio and call function directly on the headphones without having to dig your phone out of your pocket or bag.

Wrote user Bfamous, “they feel snugg and are really nice because they are adjustable and you can adjust the ear cup parts! The leather foam feels really soft and comfy.”

Riwbox CT-7S Cat Ear Bluetooth Kids Headphones

You know who absolutely won’t tolerate discomfort of any kind? Kids. These adorable cat ear headphones are not only cute, but comfortable as well thanks to their padded earcups. The small size is perfect for children, as is the fact that the volume is regulated not to surpass a certain level. The light-up cat ears are eye-catching for kids (and young-at-heart adults), though the embedded red/blue/green LED lights are only able to blink and change color with the rhythm of whatever they’re listening to in wireless mode (since the headset’s power and Bluetooth are turned off in wired mode). A glowing Riwbox Cat cartoon is interactive fun for other kids too.

Wrote user J. Bui, “The headphones are loud but not too loud for kids, the earmuffs are thickly padded and soft. It fits my 5 year old son perfectly! It also fits me and I’m a 5’7 woman!”

LETSCOM Active Noise Cancelling Earbuds

These just-released noise-cancelling earbuds come in black or white and block out up to a maximum 28dB of unwanted noise using active noise cancellation technology. Each earbud has two built-in mics that help suppress unwanted noise, and inside the earbuds are two 10mm dynamic speakers. One charge will give you up to nine hours of playback (and 27 hours total of power, when combined with the charging case. A IPX8 waterproof nano coating means you won’t have to worry about sweat or water while exercising or using by the pool, and they automatically power on when taking them out of the case so you don’t have to wait for them to connect when you put them in your ears.

User M wrote, “Even with the ergonomic left/right shape, they allow for plenty of adjustment/rotation in your ear to make them more comfortable and still get the same sound. They were super easy to pair! It usually takes a few tries to pair anything with my phone the first time, and I was still looking at the bluetooth settings when the buds said they were paired. It only took a few seconds. It automatically started playing Spotify and the sound was excellent. It is a really deep rich sound. When I only had one earbud in, it is noticeably lower quality, so I would recommend using both, plus many of the controls only work with both.”

ICOMTOFIT TWS IPX5 Earbuds

Switching from over-ear headphones to earbuds is definitely an adjustment in terms of both fit and comfort, but these ergonomically designed earbuds include three sizes of soft, flexible ear tips to ensure a secure fit. Combined with clear and balanced sound quality (and noise cancellation technology), these Bluetooth earbuds come with a rechargeable Aluminum alloy charging case featuring an LED display of the battery life. They fully charge within two hours, and support up to four hours of use.

Not for nothing, they’re also Amazon’s Choice for “comfortable wireless earbuds” and are specifically made to endure sweat and prevent damage from an intense workout.

User Dartagnan McCalister praised the sound quality and aesthetics, but especially the comfort, writing, “I am particularly in awe over the fit as I typically avoid most earphones due to the shape of my ear canal. It makes it fairly difficult to enjoy most Bluetooth devices that are meant to sit within the ear without additional support around the lobe. These come with varying sizes of earbud sleeves with those sitting already on the earbuds upon opening in “small” size, which is my perfect fit. Most others are far too large, which doesn’t allow me to wear them for extended periods of time. These fit perfectly!”

GOOJODOQ Wired In-Ear Ear Plugs Sleeping Earphones

Amazon’s Choice for “comfortable earbuds,” these wired earbuds are made specifically for long-term use at night. The soft ear plugs block background noises (from TVs to loud roommates to partners snoring), and the ergonomically designed, flexible silicone eartips come in two sizes and fit entirely in the ear for most size ear canals. They’re compatible with most devices, and they also have a multifunctional button and in-line microphone.

Wrote user Mia, “I’ve tried several versions of sleep headphones and always had the same issues. I guess the cartilage on my ears is too sensitive because the headband style was too hard – the speaker is a hard plastic disc and laying on it hurt my ears but if you moved it up/down you couldn’t hear at all. Had the same issues with other in-ear headphones that would make my ears ache by morning. But these are perfect! All pieces are soft rubber so every element has a bit of give to it, so I can lay comfortably without waking up with sore ears! I don’t even notice the cord when it’s on my pillow (inevitably you will sleep with a cord on your face).”

LUDOS Clamor Wired Earbuds

Candy-colored headphone design isn’t exclusively for larger over-ear models; these Ludos Clamor earbuds come in more than a dozen colors and, instead of plastic tips, they have memory foam pads designed to sustain wear and tear and provide long-lasting comfort. The headphones come with two different sizes of pads to ensure a custom fit.

The high-quality audio and balanced bass provide immersive sound, but user Luke Walker praised the comfort of the memory foam earbuds, writing, “This is the first pair of earbuds that claim to be ‘memory foam’ — earbuds generally hurt my ears, or fall out, or both. These stay in and they actually feel quite comfortable! Since they form nicely to the inside of my ears, I can barely hear anything except the music/sounds coming through them (They block outside noise out nicely).”

TOZO T10 Bluetooth 5.0 Wireless Earbuds with Wireless Charging Case

You can’t beat the price of these wireless Bluetooth earbuds. Both the earbuds and the charging case are waterproof up to 1 meter deep for 30 minutes, meaning they’re suitable for working out. They can last for four hours with a single charge, and the compact charging case (which can be charged wirelessly or with a USB cord) provides an additional 14 hours. They’re available in five colors, and were designed with gel-flexible silicone earcaps that come in four different sizes to ensure a comfortable fit.

A bonkers 101,167 users have given it an average rating of 4.3 out of 5, with user Vivek D. noting how much better the fit is for him than another popular wireless earbud brand. “I’m one of the very, very few people who cannot use the apple air pods. No matter how hard I try, they fall out of my ear in less than a minute. I thought I would try a different brand, and when I put these in my ear, they fell out within seconds. I was about to give up, pack up the box, and send it back, but I decided to check out the instruction manual in case i was doing something wrong. I’m so happy I did. Turns out there were 4 sizes of plastic ear caps included with the earbuds,” he wrote. “On my third try, the second smallest ones, I felt how i imagine Cinderella felt when she tried on the glass slipper. They were perfect and no matter how much I jumped up and down or shook my head, they stayed in place!”

Jarvania Bluetooth Headband Headphones

Take your sleep to the next level with this comfy headband with built-in headphones specifically meant for use while falling asleep. The bluetooth headphones can last for up to 10 hours of playback and are nestled inside a soft, durable braided cord headband with a breathable mesh lining that stretches to fit all head sizes. The slim headphones are foam-covered and less than 1/4 inch thick, making them comfortable for all sleeping positions. They’re also washable, so you can take out the speakers and clean the band — and you can use them for travel or sports too. Pull the band over your eyes and you have a built-in sleeping mask as well.

Writes user Ado, “I have been using a wired sleep headband for a while but the wire started to wear out. Just got this yesterday and used it for the first time last night, and it worked great. Sound quality worked perfectly with my white noise sleep app, and the battery life lasted all night. Easy to connect to Bluetooth too. Breatheable and comfortably to sleep in.”

LETSCOM U8I Bluetooth Headphones

These waterproof wireless earbuds are specifically made for sports, so the internal nano-coating protects the headphones from heavy rains or sweat. And while they’re wireless and use Bluetooth technology, they are connected by a cord to prevent any lost earbud tragedies while working out. The earths come in four sizes, and they come with a carry bag, a micro USB cable, and a wire clip.

User Somer Durr liked the different sizes of eartips, writing, “They feel great on and are very secure even when I’m running on the treadmill.”

JVC Gumy in Ear Earbud Headphones

Just because you want a budget pair of earbuds doesn’t mean you need to sacrifice comfort. These might be cheap, but they come with three different sizes of silicone eartips and are comfortable enough to wear in bed. They’re compatible with Android smartphones and iPhones, and have a 3.3′ color cord with gold-plated 3.5mm headphone plug.

Wrote user Linda, “I hate having anything in my ears, but these are the most comfortable earbuds I have found. Perhaps because they have such a soft earpiece. It forms to your ear with no effort on your part. Bad thing is, when I’m listening to a book, it’s too easy to go to sleep while listening. Then it’s the search back to where my brain checked out. They are comfortable and have really good sound at a good price.”

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