Most Comfortable Headphones in 2023: A Guide to Pain-Free Headphones

Most Comfortable Headphones: A Buyer’s Guide to Pain-Free Headphones and Earbuds

Affiliate Disclosure: When you buy a product via our links, we sometimes earn a referral fee. Learn more

Pretty much everybody here at Speakergy loves music. Sure, we all love great gear and great sound, but mostly because it helps us get closer to the music itself. In fact, I think it is fair to say that we all, and probably most of our listeners, may count music as the greatest pleasure in our lives.

But what if that pleasure is frequently experienced with discomfort? What if, as happens way, way too often, the headphones we are listening to are so uncomfortable that they actually cause us pain or keep distracting us from our listening and the unalloyed pleasure it should bring?

One of the headphone questions we hear most is about this exact topic, and usually takes one of several basic forms:

  • What are the most comfortable headphones I can get?
  • What are the most comfortable earbuds I can get?
  • Why are my headphones/earbuds so uncomfortable?
  • Is it normal to feel pain when listening to headphones?
  • Is Lady Gaga to Blame? 😂

And, sad as it may sound, we have to say that while it is not normal to feel pain from headphone listening, it happens far too often. But again, music is supposed to be about pleasure – even EMO, Punk, and the redoubtable LG, I guess – and so we have put together this in-depth buyer’s guide to the most pain-free headphones and earbuds available in 2023.

What Makes Headphones Comfortable or Uncomfortable?

There are lots of ways either standard or in-ear headphones can be uncomfortable (including even some otherwise well-made premium models) including:

  • Physical Pain in the ears, in the ear canals, or on the top of the head
  • Slipping and sliding, not staying in or on the ears
  • Harsh, distorted sound, and the pain and fatigue it can cause
  • Too-heavy headphones
  • Too-large earbuds

Many headphone manufacturers, however, really work to make their headphones more and more comfortable and have addressed several important factors, including:

  • How much pressure do the cups place on your ears – not so much that they will hurt, or so little that they will slip
  • The design, angle, and materials of earbud tips – making sure they are comfortable and yet stay in place
  • The size of earbud tips and bodies
  • The size and weight of headphones
  • The softness and adjustability of headbands and ear pads
  • Warm, pleasing sonic qualities that aren’t harsh or fatiguing, but are nonetheless accurate and neutral and don’t mask or smooth over detail or musical cues
  • The overall quality of the headphones and the resultant long-term stability of all of these factors

How Can You Find the Most Comfortable Headphones?

Pain and discomfort while listening can be caused by many factors, but there is always a common element – that painful, uncomfortable headphones take us away from our listening enjoyment.

And since listening enjoyment seems to be at least a big part of our lives (aren’t we lucky?), it is important to find and get headphones that won’t physically hurt when we’re wearing them, and won’t hurt our ears with harsh and fatiguing sound, and won’t keep annoying us by slipping, coming unseated or even falling off.

So we’ve done tons of comparisons, and in addition to our own experiences, we have also read countless customer reviews from Amazon and other sites, and have come up with 20 great choices, in-ear buds and standard headphones that are extremely comfortable, both for short-term and long-term listening and sound absolutely great.

With so many choices for the best headphones for comfort, we’ve broken down the list into four basic categories:

  • Most Comfortable Earbuds – Wired
  • Most Comfortable Headphones – Wired
  • Most Comfortable Earbuds – Wireless
  • Most Comfortable Headphones – Wireless

In each category, we will have at least one budget, mid-priced and premium recommendation. In addition, we will have a final category for the most comfortable audiophile headphones on the market today, with just one recommendation (which, you may have guessed, isn’t exactly budget or mid-priced).

So, if you are sick and tired of feeling pain and discomfort when you listen to headphones or earbuds, you’ve come to the right place. Just figure out if you want wired or wireless, on-ear or in-ear, and what price level would cause you the least discomfort, and you will find the best possible choice below. 

Listening to music should be pain-free, and so should shopping for the most comfortable headphones!

Most Comfortable Headphones on the Market in 2023

Most Comfortable Wired Earbuds – Budget

These least expensive Panasonic ErgoFit headphones are possibly the most often recommended earbuds on the market today, and for two very specific reasons:

  • They are extremely comfortable for in-ear headphones
  • They are incredibly musical, warm, accurate, and engaging

People consistently report that they can wear and listen to the ErgoFit headphones for hours and hours with no discomfort whatsoever and that the buds not only are pain-free but stay secure and thus avoid the annoyance and reduction of sound quality slipping can cause. 

People also say that they actually listen to their more expensive headphones less and less, and these budget Panasonics more and more – they are just so small, easy, and comfortable, and have such a wonderful musical character.

The TCM120 does not have a microphone, and the TCM125 has one, but other than that they are identical, and either way they are our choice for the most comfortable budget-wired earbuds in 2023.

Most Comfortable Wired Earbuds – Mid-Priced 

1MORE Triple Driver In-Ear Earphones Hi-Res Headphones with High Resolution, Bass Driven Sound, MEMS...
  • Three Drivers- These Headphones Have Two Balanced Armatures And A Separate Dynamic Driver. Together They Deliver An Extremely Accurate...
  • Product Note : If the size of the earbud tips does not match the size of your ear canals or the headset is not worn properly in your ears,...
  • Tuned By A Grammy Award Winning Sound Engineer- 1More Collaborated With Internationally Acclaimed Producer, Mixer, And Sound Engineer Luca...
  • Comfortable Ergonomic Design- The Oblique Angled Ear Fittings Naturally Match Your Ear Canals. 9 Sets Of Included Ear Tip Sizes Ensure A...
  • Intelligent Control Technology- In-Line Remote Control Is Conveniently Located Allowing You To Effortlessly Control Volume, Select Songs,...

Offering an essentially high-resolution listening experience at a very low price, the 1MORE triple drivers have gained quite a status among budget audiophiles, who praise their deep bass, neutral and accurate character, excellent dynamics and transient response, and overall sweet and musical sound.

But the 1MORE triple driver in-ear headphones are also known as the most comfortable and secure fitting earbuds in their class, which allows for long, pain-free listening sessions with consistently high-quality sound.

A brilliantly accurate and engaging headphone musically, with a complete lack of glare or harshness and an ideal ergonomic design, the 1MORE triple driver in-ear buds are our choice for the most comfortable mid-priced wired earbuds in 2023.

Most Comfortable Wired Earbuds – Premium 

Shure SE535LTD Professional Wired Sound Isolating Earbuds, High Definition Sound + Natural Bass,...
  • SOUND ISOLATING TECHNOLOGY - Own your audio space with sound isolating design that blocks up to 37 dB of noise to eliminate distractions....
  • CUSTOMIZED FIT - Includes three sizes (S, M, L) of the flex and black foam sleeves. Experiment with the size and style that creates the best...
  • SECURE, OVER-THE-EAR DESIGN - Wireform fit ensures earphones stay in place and cables remain out of the way.
  • STRIKING FULL-RANGE SOUND - Full range sound from a triple high-definition driver to deliver accurate, natural sound in a discrete, durable...
  • DURABLE REINFORCED CABLE - Detachable cable is durable enough to withstand everyday wear, yet allows for easy replacement in case of damage....

Shure has been around for a long, long time, and has long been known for having both the best value in high-end audio products and the best high-end products period – the legendary Shure V15 stereo phonograph cartridge, for example, counts as one of the best cartridges ever made and one of the best value audiophile products ever sold. 

These days Shure’s still excellent reputation is largely based on their amazing in-ear monitors, and particularly on the truly beautiful sounding SE535LTD earbuds, which are known for their amazing neutrality, resolving power, detail and micro-detail, musical energy and life, precise imaging and huge soundstage, and wide, flat frequency response. And, to make sure you can enjoy this amazing sound, they are equally known for their incredibly comfortable and secure fit.

The most amazing thing about these super-premium audiophile buds is how they disappear, with such a high level of comfort and essentially no glare, harshness, or distortion to get between you and your listening. They are a favorite earbud for many of us here at Speakergy, a great value for a high-end, high-resolution in-ear monitor, and an easy choice for the most comfortable premium wired earbuds in 2023.

Most Comfortable Wired Headphones – On-Ear or Over-Ear

For standard wired headphones, we will divide our choices into two sub-categories – open-back and closed-back.

Closed-back headphones make more sense for most of us, since they isolate us much more from the ambient sounds around us, keep our music from leaking out and potentially bothering others, and the best designs can be really comfortable.

Open-back headphones don’t isolate as well and will let whatever we’re listening to pretty easily be heard by those around us, but since they are open in design they are actually cooler to wear over a long time and put less pressure on our eardrums – especially with loud music.

Check out our article on the difference between open-back and closed-back headphones.

And while closed design headphones can sound amazing, open designs do sound a little better, with a larger and more precise stereo soundstage and a kind of general ease and musicality that is often quite exquisite – a wonderful choice, if you can get away with them!

Most Comfortable Wired Headphones – Closed Back

Most Comfortable Closed Back Headphones – Budget

Sony ZX110 Over-Ear Dynamic Stereo Headphones (Black)
  • 30mm drivers for rich, full frequency response
  • Lightweight and comfortable on-ear design
  • Swivel-design for portability
  • 47.25-inch (1.2 m) tangle-free, Y-type cord

These extremely light Sony headphones have a great overall design for comfortable and pain-free long-term listening, and the soft earpads put just the right amount of pressure on your ears, so that they don’t hurt but also don’t slip or fall off.

But comfort is just one reason we are recommending the Sony ZX110 wired headphones (the ZX110AP are the same but with a built-in mic for phone use) – these headphones have one of the most dynamic, energetic, and exciting sounds we’ve ever heard at this price, with really deep and strong bass and an overall rich and warm character that is at the same time open and detailed.

An amazing value, the Sony ZX110 on-ear headphones are quite cheap, well built, sound amazing, are super comfortable, and are our choice for the most comfortable budget-wired headphones with a closed-back design.

Most Comfortable Closed Back Headphones – Mid-Priced

AKG Pro Audio K92 Over-Ear, Closed-Back, Studio Headphones, Matte Black and Gold
  • Precisely Balanced Response Provides Reference-Monitor Accuracy
  • Professional 40Mm Drivers For Extended 16Hz - 20Khz Frequency Response
  • Over-Ear Design And Lightweight Construction For Exceptional Comfort
  • Closed-Back Design Maximizes Isolation
  • English (Publication Language)

A highly regarded and popular opening-level set of audiophile headphones, the AKG K92 has a very neutral, accurate, warm, and rich sound that rewards long, close listening.

While the frequency response is quite flat, making them ideal for classical, jazz, and acoustic tracks, the K92 phones have lots and lots of extended deep bass and can sound just amazing with all kinds of popular music as well – not as bass-heavy out of the box as most bass-head favorites, but they can be equalized to sound as bass-rich as any of them – and better overall.

The wide, self-adjusting headband works great, as do the strong but never-tight feeling bands and ear cups, and the AKG K92 headphones are really light for their size

Comfortable to wear, and even more comfortable to listen to, the AKG K92 full-sized headphones are our choice for the most comfortable mid-priced wired headphones with a closed-back design – and, regardless of their very low price, one of the best sounding, most musical headphones on our list.

Most Comfortable Closed Back Headphones – Premium

Audio-Technica ATH-M70X Closed-Back Dynamic Professional Studio Monitor Headphones, Black
  • Tuned for extremely accurate reproduction and carefully crafted using key metal components for lasting durability
  • Proprietary 45 millimeter large aperture drivers are tuned to accurately reproduce extreme low and high frequencies (5 to 40,000 Hertz)...
  • Ideal for studio mixing and tracking, FOH, DJing, mastering, post production, audio forensics and personal listening
  • Circumaural design contours around the ears for excellent sound isolation in loud environments
  • Equipped with 90 degree swiveling earcups for easy, one ear monitoring

People tend to get pretty picky and critical when spending several hundreds of dollars on headphones, and so it is amazing to see just how glowingly positive the customer reviews for these Audio-Technica M70X headphones are – at least until you hear them, then it all makes sense. Their punchy, tight, and fast sound makes everything sound amazing, with intense energy, liquid musicality, and incredible detail and resolution. And somehow they do this without changing anything, being one of the most absolutely transparent and neutral headphones available under a thousand dollars and simply letting the natural beauty and quality of the recorded music shine through.

Of course, we should also say that they are unbelievably comfortable, and not just for big headphones like this. I have worn a pair for hours without even thinking about them – which is another way these superb audiophile ‘phones simply refuse to get between you and the music.

A wonderful pair of headphones in every way, and fully worth their not-insubstantial price tag, the Audio-Technica ATH-M70X studio monitor headphones are our choice for most comfortable premium wired headphones with a closed-back design.

Most Comfortable Wired Headphones – Open Back

Most Comfortable Open Back Headphones – Budget

Koss Porta Pro On Ear Headphones with Case, Black / Silver
  • Designed for deep bass performance
  • Comfortable, secure fit with adjustable headband and multi-pivoting earplates
  • Two adjustable temporal-comfort zone pads shift the pressure and perfectly balance the ear plates on your ear
  • Collapsible for maximum portability, includes carrying case
  • Connector Type: 1 x Headphones (mini-phone stereo 3.5 mm)

A legend among audiophiles for more than three and a half decades now, the marvelous little Koss Porta-Pro headphones have remained essentially unchanged in all that time, and still feature on pretty much every serious audiophile publication’s best-of list as the best budget headphones.

Their diminutive size belies the Porta Pro’s ability to pump out really deep, fast, and solid bass, the mids are silky smooth and sweet, and the highs shimmer with a clarity and detail that never even hints at glare or harshness. Their open-back design affords the music a kind of transparency and ease normally associated with much (much, much) more expensive ‘phones.

And the Koss Porta-Pro headphones are so small and light, and so well designed ergonomically, that you may well forget you are even wearing them. An obvious choice for the most comfortable budget-wired headphones with an open-back design.

Before we move on to the best mid-priced headphones for comfort, I should say that for a few dollars more you can also get the amazing AKG Pro Audio K240 Studio Headphones, which are a full-sized, semi-open design and stand as the only ‘phones I know that clearly give the Porta-Pros a run for their money – for sound quality and for comfort – without, again, spending a lot more. 

Most Comfortable Open Back Headphones – Mid-Priced

beyerdynamic DT 990 Pro 250 ohm Over-Ear Studio Headphones For Mixing, Mastering, and Editing
  • Open over-ear headphones, ideal for professional mixing, mastering and editing
  • Perfect for studio applications thanks to their transparent, spacious, strong bass and treble sound
  • The soft, circumaural and replaceable velour ear pads ensure high wearing comfort
  • Hard-wearing, durable and robust workmanship - Made in Germany
  • Practical single-sided cable (3.0m coiled cable)

We’ve made quite a jump in price to arrive at our choice for the most comfortable mid-range headphones, but given the quality of the Koss and AKG headphones listed above these stunning Beyerdynamic DT 990 phones were the only meaningful choice – all of the ‘phones we know of in-between don’t sound nearly as good or feel as comfortable to wear.

But the DT 990 are another story – like a new level of lightness and ease has magically been bestowed, both in terms of wearing comfort and sound. With great sounding recordings and high-resolution sources the Beyerdynamics 990 are at once the most honest and the most exciting headphones we’ve heard anywhere near the price, and even average or bad quality sources – like poor MP3 files or lots of YouTube audio tracks – somehow sound much better.

The DT 990 phones are not only completely free of any glare, haze, or distortion, and all of the attendant risks of listening discomfort and fatigue but they are designed and built to the standards of professional studio use, meaning they can be worn for hours and hours without the slightest trace of discomfort or pain.

Easily one of the best-sounding mid-priced headphones ever made, and one of the best values on our list, the Beyerdynamic DT 990 are our choice for the most comfortable mid-priced wired headphones with an open-back design.

Most Comfortable Open Back Headphones – Premium

SENNHEISER HD 660 S - HiRes Audiophile Open Back Headphone
  • Reference class open back, dynamic headphone employing new and improved transducers delivering low harmonic distortion
  • Transducers are hand selected for precise (1 dB) left / right matching tolerance insure exceptional accuracy and presentation of stereo...
  • 150 ohm nominal impedance allows direct connection to home and mobile Hires audio devices. Contact pressure: 6.0 N - 1 N
  • Para aramid reinforced, detachable cables employ high conductive OFC copper to insure signal integrity with very low handling noise
  • Supplied with two connection cables: One with a 6.35 millimeter stereo plug, the other a 4.4 millimeter Pentaconn balanced stereo plug. Also...

For many years the default choice of somewhat budget-conscious audiophiles has been the Sennheiser HD 650 headphones, which users consistently swore were the most neutral, high resolution, detailed, dynamic, and fun headphones they had ever used – indeed, they were often compared to audiophile cans costing several thousands of dollars and, sometimes at least, were claimed to be better.

Recently Sennheiser discontinued the beloved HD 650s and introduced their replacements – the HD 660 – and I can tell you, everybody was pretty nervous! Turns out, though, that the new 660 has everything their famed predecessors had and much more. They have the same beloved, musically sweet, and engaging sound, with even greater speed, wider and more precise imaging, more detail, and a better ability to resolve both the smallest nuances and the most complex music, and even more engaging and dynamic overall presentation. Really, even the most die-hard HD 650 fans eventually admitted that these new 660 headphones are better.

One of the things the army of fans loved about their 650 ‘phones was that not only were they musically engaging and delightful to listen to, but they were also so well designed that the engagement and delight could last for hours and hours without any discomfort or pain. Turns out that in this respect too the new Sennheiser HD 660 headphones are even better, and one of the most comfortable full-sized headphones made.

A new legend in the making, the Sennheiser HD 660 S headphones are sure to be wildly popular (in fact they already are) and are our choice for most comfortable premium wired headphones with an open-back design.

Most Comfortable Wireless Earbuds

With everything these true wireless earbuds offer – up to 40 hours of battery life, 5.2 Bluetooth, a crystal clear microphone with CVC noise reduction, smart design, and extreme comfort – and for their extremely low price, we’d be happy to leave it at that and recommend them wholeheartedly. 

But the Boltune BT-BH020 in-ear headphones also have just amazing sound quality. Not, of course, competitive in most ways with the really high resolution ‘phones and buds on our list of most comfortable headphones, the 20s do manage to express the same kind of musical energy, honesty, and beauty that characterizes the best headphones on the market, and are an incredibly enjoyable and rewarding listen.

High-tech in-ear buds with great features and great sound, at a very low price, and one of the most wearable true wireless headphones we’ve come across, the Boltune BT-BH020 earbuds are our choice for the most comfortable budget wireless earbuds in 2023.

Most Comfortable Wireless Earbuds – Mid-Priced 

Soundcore Anker Liberty Air 2 Pro True Wireless Earbuds, Targeted Active Noise Cancelling, PureNote...
  • Pure Sound via Targeted Active Noise Cancelling: Choose your scenario via the Soundcore app and listen as ambient sounds disappear to leave...
  • PureNote Driver Technology: Get a 45% boost to your bass, and a 30% wider frequency bandwidth than ordinary drivers. Drivers coated with 10...
  • LDAC Technology: Compared with standard Bluetooth codecs, LDAC is capable of transmitting 3 times more data—ensuring no detail is lost...
  • Up to 26 Hours of Playtime: Get 7 hours of playback from a single charge on the earbuds with up to 3 recharges from the charging case.

The Anker Soundcore Liberty Air 2 Pro earbuds, in addition to having one of the longest names of all our choices for most comfortable headphones, are noteworthy in many other ways and end up being one of our favorite recommendations and favorite wireless earbuds.

For one thing, the Liberty Air 2 Pro buds are just a great looking and great feeling product, with a beautiful fit and finish and an overall really premium feeling. The sound is beautiful too, with all the bass and energy any popular music demands and the kind of clarity, detail, and pinpoint imaging that serves classical and jazz equally well. Overall, for any kind of music, the sound is sweet, musical, and eminently likable.

And with 9 (!) pairs of ear tips, from XXXS to XL, the Pros will fit any size ear comfortably. More than that, though, their great design, smooth finish, perfect angle, solidity, shape, and size make them among the most comfortable true wireless buds on the market today.

Bluetooth 5, 26 hours of total battery life, active noise cancelation, six phone mics, and the absolutely brilliant HearID app for customized analysis and equalization are just icing on the cake and make the Anker Soundcore Liberty Air 2 Pro true wireless in-ear headphones our clear choice for the most comfortable mid-priced wireless earbuds in 2023.

Most Comfortable Wireless Earbuds – Premium

Bose QuietComfort Noise Cancelling Earbuds-Bluetooth Wireless Earphones, Triple Black
  • Noise cancelling earbuds – Engineered with the world-class noise cancelling. Bose controllable noise cancellation and full...
  • High-fidelity audio – An exclusive acoustic architecture brings your music, podcasts, and videos to life, while...
  • Comfortable wireless earbuds – Three sizes of StayHear Max eartips are included for a secure fit. Crafted from soft silicone, they...
  • Simple touch controls – It’s as easy as tap, swipe, or press. Control your noise cancellation settings, pause, play, and...
  • Noise-rejecting microphones – Tiny microphones work together to focus on your voice, filtering out surrounding noises for fewer...

With by far the most advanced and effective noise reduction on the market today, and the legendary Bose sound, the QuietComfort 35 earbuds don’t really need any additional recommendations, but we would be remiss not to include these great buds on our list of best earbuds for comfort. 

With a smooth and dark sound that is probably the least fatiguing you can get under a thousand dollars, but that never fails to light up any music with a kind of detail and energy that has often been duplicated but that no other manufacturer has ever come even close to, the Bose QuietComfort 35 truly wireless earbuds really stand alone – or better to say that they stand proudly with all Bose products, and offer a unique musical sound in their category.

The Bose QuietComfort 35 in-ear headphones also offer, again, simply the most advanced, versatile, and effective noise canceling currently available – amazing even compared to other Bose products – and in every way is a technological tour de force. And with their brilliant ergonomic design and extreme wearability, they are an easy choice for the most comfortable premium wireless earbuds in 2023.

Most Comfortable Wireless Headphones – On-Ear and Over-Ear

Most Comfortable Wireless Headphones – Budget 

JBL TUNE 500BT - On-Ear Wireless Bluetooth Headphone - Black
  • WIRELESS BLUETOOTH & MULTI-POINT CONNECTIONS: Wirelessly stream high-quality sound from your smartphone without messy cords. Allows you to...
  • JBL PURE BASS SOUND: Wireless headphone features the renowned JBL Pure Bass sound, which can be found in the most famous venues all around...
  • HANDS FREE CALLS: Easily control your sound and manage your calls from your bluetooth headphones with the convenient 1-button remote with...
  • UP TO 16 HOUR BATTERY LIFE WITH SPEED CHARGE: For long-lasting fun, listen wirelessly for up to 16 hours and recharge the battery in as...
  • COMFORT FIT DESIGN: The lightweight materials and soft ear cushions with a padded headband make the bluetooth headphones comfortable to wear...

The JBL Tune 500BT on-ear wireless headphones are a really fun-sounding pair of ‘phones for a really low price. They are punchy and exciting, with a bright sound that is never edgy or harsh and with lots of bass, and they have plenty of resolution, detail, and subtlety to beautifully reproduce any kind of music, from hard rock to full orchestral recordings, hip hop to small ensemble acoustic jazz.

The Tunes are also a very light, comfortable headphone, with thick, soft, and durable premium ear pads and just the right amount of pressure on the ears to keep them in position but never cause pain or discomfort, and being on the ear they never get hot or put too much pressure on your eardrums the way some over-ear headphones can.

JBL quality, a smart and stylish design, fun and exciting sound, and real long-term comfort all add up to make the JBL Tune 500 BT our choice for the most comfortable budget wireless headphones in 2023. 

Most Comfortable Wireless Headphones – Mid-Priced

Sennheiser HD 4.50 BTNC Bluetooth Wireless Headphones with Active Noise Cancellation, Black and...
  • Bluetooth 4.0 and aptX technologies to deliver exceptional wireless sound quality..Connectivity Technology: Wireless
  • NoiseGard active noise cancellation to reduce ambient noise levels improving the listening experience
  • Intuitive ear cup mounted controls for changing tracks and for making calls via the integrated microphone. Frequency response (Microphone) :...
  • Up to 19 hour battery life with Bluetooth and NoiseGard activated and is supplied with connecting cable for battery free listening
  • 2 year warranty when purchased from an authorized Sennheiser dealer

For a very reasonable price, the Sennheiser HD 4.50 headphones offer not just extreme comfort, active noise reduction, great styling, and a premium look and feel, but most importantly they have that superb Sennheiser sound. 

In fact, while they have the older 4.2 Bluetooth chipset, which offers a lower range than the Bluetooth 5 offered in the Bose QuietComfort phones below, and a slightly less effective (though still great) active noise reduction than the Bose, I would be tempted to say that the Sennheiser sound better – more open and honest, with a slightly better ability to resolve tiny nuances in dynamics, space and time. And, let’s not forget, at less than half the price.

The Bose 35 II phones have more bass, and a more “popular” overall sound signature, but the Sennheiser 4.50 wireless has more deeply extended bass, a wider and flatter overall frequency response, and is actually much more versatile, sounding superb with all types of music. And the AptX codec means that you can play even high-resolution music files, like HD 24-bit digital downloads, without any loss in sound quality.

Sorry, I got so excited talking about how these wonderful ‘phones sound, that I kind of forgot why we’re here, but be assured that these are, especially for big, over-ear headphones, really comfortable even during long listening sessions. I have used them extensively and have never felt any pain or discomfort – in fact, I most often kind of forgot I was even wearing them, and just fell into the music itself.

This, in itself, makes the Sennheiser HD 4.50 Wireless Noise Cancelling Headphones my choice for the most comfortable mid-priced wireless headphones in 2023.

Most Comfortable Wireless Headphones – Premium

Bose QuietComfort 35 II Wireless Bluetooth Headphones, Noise-Cancelling, with Alexa Voice Control -...
  • Three levels of world-class noise cancellation for better listening experience in any environment
  • Alexa-enabled for voice access to music, information, and more
  • Noise-rejecting dual-microphone system for clear sound and voice pick-up
  • Balanced audio performance at any volume
  • Hassle-free Bluetooth pairing, personalized settings, access to future updates, and more through the Bose connect app. USB cable: 12 inch

There are so many articles and reviews claiming that this or that brand or model are better noise canceling headphones than Bose, but if you have compared these Bose QuietComfort 35 series II ‘phones to any competition at or even above this price level you know the real story.

The Bose 35 is by far the most comfortable, they sound more open and musical, and they have more effective noise canceling, which has much less of an effect on sound quality, than any of the other major brands.

The Bose sound is, in fact, the stuff of legends, from the first crazy looking 901 direct/reflecting loudspeakers more than 50 years ago. Even then, the smooth and warmly musical sound was evident, and it has just gotten better – the QuietComfort 35 II having more dynamic, detailed, and accurate, with amazing resolution and an uncanny presentation of music in space and time, and still with that same smooth, warm character.

The noise reduction is, of course, freakishly and inexplicably effective in all kinds of environments, and adds to the overall comfort of using the 35s, and with their first-quality ear pads, great overall design and engineering, and just the right amount of pressure, this one of the most comfortable full-sized headphones of any type that we’ve used.

I could go on and on about the advanced technology and features, and I can’t really say enough about the comfort, the sound quality, and the amazing noise reduction, so suffice it to say that the Bose QuietComfort 35 series II were without any serious competition in our choosing the most comfortable premium wireless headphones in 2023.

Most Comfortable Audiophile Headphones

HIFIMAN Arya Stealth Magnet Version Full-Size Over-Ear Planar Magnetic Headphone for...
  • Acoustically Invisible Stealth Magnet: Unlike the sound waves created by a conventional magnet, the special shape of Stealth Magnets enables...
  • Nanometer Thickness Diaphragm A breakthrough core technology developed by HIFIMAN and first of its kind in headphone application. Working...
  • Metal and High-Grade Plastic Construction: HIFIMAN designed the Arya's high-quality metal headband with extra strength and a special...
  • Patented “Window Shade” System: Created to meet the need for driver protection and an optimized open-back design. Asymmetrical Ear Cups:...
  • Bold Black Aesthetic: With its classic HE1000-style shape combined and striking good looks of its all-black exterior, glossy black headband,...

I remember once, many years ago, I had the chance to listen to a pair of Stax SR-80 Electret Headphones with their dedicated SRD-4 transformer box. When I tried them they were already long discontinued, and something of an antique and curiosity, but in their day they were known as probably the very best sounding headphones ever made.

They were also incredibly big, bulky, heavy, awkward, uncomfortable, and, after a while, downright painful, and made me realize what people had to go through 40 years ago for true audiophile sound from a pair of headphones.

But now we flash forward four decades and land on the Hifiman Arya open-back headphones and, to paraphrase a commercial from the time of the Stax SR-80s, we’ve come a long way, baby!

While they may not be absolutely the best sounding headphones ever, or even the best sounding currently available (both of those honors doubtless go to the much more expensive Hifiman Susvara headphones), the Arya is still one of the five or six best headphones currently made, and easily the most comfortable true high-resolution audiophile headphones on the market today – in that respect, about as different from the Stax as it is possible to be. 

That is, to me, the most brilliant thing about the Hifiman Arya headphones, that they not only have absolutely breathtaking sound but allow you to fully fall into that sound for as long as your heart desires, with no pain, discomfort, or distraction to pull you out.

And yes, the flagship Hifiman Susvara, and maybe one or two other super-expensive ‘phones have marginally better sound, but the Arya is, without doubt, one of the very best, most musical, accurate, and exciting high fidelity products of any kind ever made, and at a mere $1,600 they stand as one of the best values in high-end audio today. They are our choice for the most comfortable true audiophile headphones in 2023.

Closing Thoughts: The Perfect Earbuds for All of You Really Tough Cases

We recently published an in-depth buyer’s guide to the best and most comfortable wireless earbuds for people with very small ears, and if this describes you, you might well find even more helpful information in that article – title/link.

One of the most interesting and helpful products listed there was the Ultimate Ears Fit True Wireless Custom Fit Earbuds, which have a unique self-forming ear tip that forms itself to the unique shape and dimensions of your ear canal and sets into shape so that you will always have the most secure and most comfortable fit. 

This is an especially welcome advancement, and a great product, for people with small ears, but the very nature of these brilliant earbuds means that they work equally well with any ear – regardless of its size, shape, or even irregularities. And if your left and right ears are different, each earbud tip will form differently.

If you’ve been suffering from pain and discomfort with headphones or earbuds, any recommendation on our list will be a great improvement and offer truly comfortable and pain-free listening, and great sound as well, but if you have always had particular difficulty finding comfortable in-ear buds, or even making earbuds fit or work at all in your ears, the Ultimate Ears Fit may be just the product you’ve been looking for.

They are also just great sounding headphones, and the sound will in fact be much better – with these or any earbuds – when you finally get a good, tight, and lasting fit. They are great earbuds in every other way as well, with Bluetooth 5.0, 20 hours total battery life, compatibility with Siri and Google Assistant, and sweat-resistant design, and are highly recommended.