The Most Comfortable Headphones for 2021

Comfort is high on the list of priorities for many people when buying a set of headphones.  That shouldn’t come as much of a surprise as we now spend more time-consuming media from portable devices than ever before. When you get on and bus, train, or plane, and you will see countless people with their headphones on for the duration of their journey.  We are talking about people wearing headphones for long listening sessions, usually in a variety of situations.

Similarly, many offices around the world are full of people consuming music, podcasts, and ebooks at their desks. The fact is we can spend a lot of time listening, and the last thing you want is pain or discomfort, which is something cheap or poor-quality headphones can cause. 

With so many people asking us what the most comfortable headphones are, we have finally decided to put together this list of the best models that will hopefully make your listening experience more fun. Below you will find not only the list of our recommendations but some handy tips and tricks that will help you reduce/eliminate pain and discomfort.

Comparison Table

Test Winner
Bose Noise Cancelling Headphones 700, Bluetooth, Over-Ear Wireless Headphones with Built-In Microphone for Clear Calls & Alexa Voice Control, Black
Blue Sadie Premium Headphones with Built-in Amp (formerly called Mo-Fi)
Most Comfortable Earbuds
Final Audio Design High Resolution Headphone - Stainless Steel (E3000) Black
Bose 700 ANC
Blue Sadie
Final Audio E3000
Editors Notes
The most comfortable headphones I have ever used. Lightweight materials and airy pads make them a joy to use.
An unusual design but on that ads a lot of comfort. The headband and padding are very generous and for a full size headphone they are very light.
An earbud so small it disappears in your ear. The sound is also fantastic given how cheap they are.
Test Winner
Bose Noise Cancelling Headphones 700, Bluetooth, Over-Ear Wireless Headphones with Built-In Microphone for Clear Calls & Alexa Voice Control, Black
Bose 700 ANC
Editors Notes
The most comfortable headphones I have ever used. Lightweight materials and airy pads make them a joy to use.
Blue Sadie Premium Headphones with Built-in Amp (formerly called Mo-Fi)
Blue Sadie
Editors Notes
An unusual design but on that ads a lot of comfort. The headband and padding are very generous and for a full size headphone they are very light.
Most Comfortable Earbuds
Final Audio Design High Resolution Headphone - Stainless Steel (E3000) Black
Final Audio E3000
Editors Notes
An earbud so small it disappears in your ear. The sound is also fantastic given how cheap they are.

Comfortable Headphones Buyers Guide and FAQ

Choosing Comfortable Headphones

The most important factor in choosing headphones is the design’s physical properties and ergonomics.  It is great having amazing-sounding headphones, but how they fit into your head shape is extremely important. It plays a big role in how often and for how long you will want to use them. There are so many headphones on the market today that this can be a very daunting prospect. For many people purchasing a new set of headphones is a fairly large purchase, so you must get the most from it.

The biggest problem we have in 2021 is the move of retail to online. Few stores have physical sets of headphones that you can try on and examine yourself in person. When shopping online, you don’t have the advantage of trying multiple sets of headphones searching for the one that fits you best.

For this reason, we suggest you purchase from companies with good return policies in case you find the headphones you have purchased are uncomfortable, and you don’t think you will get along with them long term.

Considerations: What makes a comfortable headphone?

Lightweight headphones are usually the most comfortable!

Generally speaking, lighter headphones are more comfortable than heavy ones.  A lighter headphone will cause less strain on your muscles in supporting their weight. Even something as insignificant as a few grams can make the difference in fatigue to the neck muscles and support posts of the head. 

It’s not often thought about, but if you look at it, logically, you are adding a ballast that shifts weight distribution on top of your neck. Whilst over an hour or so, you might not notice any difference over longer listening periods, this cumulative effect adds up and can cause soreness, headaches, and even permanent postural imbalances.

In terms of earphones, weight plays a different factor in discomfort.  They actually tug on the earbuds making them more apparent to your subconscious of them being in your ears.  A heavy set of earbuds has more potential to shift in the canal and fall out.

Clamping Pressure can have a dramatic effect on long-term discomfort.

This applies only to over-ear headphones but is a major factor in how comfortable your headphones are.  Clamping pressure is the force in which the headband pushes against your head.  You want enough clamping force so that a seal is made and external noise is reduced, but you don’t want so much that it becomes fatiguing over time.  DJ headphones such as Sennheiser’s HD-25 are notoriously hard clampers by design, and that makes them perfect for use in a club or studio but not for casual, relaxed listening.

Jason Lim of Washinton state has conducted studies into the optimum design for headphone headbands to find the optimum level of performance. This paper showed that companies have to walk a fine line about balancing a sturdy and robust headphone design against a user’s comfort within a set parameter of costs.

There will be trade-offs you have to make in this area in terms of durability and comfort.

Earpads, Ear-Tips & Headband – The Points of Contact

These are the contact points of the headphone and obviously one area that can make all the difference.  Earpads should be comfortable in terms of padding and be breathable enough to prevent the build-up of “hot spots.”

Eartips are crucial to forming a seal in the ear canal, and luckily most earphones come with plenty of options for you to achieve an optimum fit.  Should you not be able to get to grips with any of the included ear tips, then you can start tip rolling, a process of trying different aftermarket tips, to find the perfect set for you.  We recommend these Comply and Spinfit models. Both make excellent tips with unique design features that can improve comfort.

The headband is the point that joins the two earcups, and in the case of most headphones, it sits directly in contact with the top of the head.  Some companies increased comfort by adding extra padding, and some use an elastically suspended leather bridge.  Some companies do a great job, but others can cause real pain if your head is in the wrong shape.

Sonically Comfortable Headphones – Tuning and Tone

What is sonic comfort? Honestly, it’s a term I just made up, but I think it fits the bill for what I am about to discuss. 

Without getting too in-depth on the properties of sound and the effects of different frequencies on your long-term listening pleasure, I think it’s pretty important. 

Some frequencies, when listened to over long periods of time, become fatiguing.  One of the most common ways a headphone becomes “Sonically Uncomfortable” is if it displays sibilance.  To many people, excessively pushed treble is like nails on a chalkboard and can only be tolerated in short bursts. 

Excessive bass and loose bass can also have a big effect on how long you can listen, as, over time, it feels like your head is being jackhammered.

So then, when choosing a set of headphones based on comfort, we want to have something that is relatively inoffensive, with a smooth presentation and sound.  Thankfully more and more headphones have this, and all the headphones listed below have very pleasant sound signatures. 

What is better for comfort? In-Ear Headphones (Earbuds/Earphones) versus over-ear headphones

Really, take your pick on how you want to use your headphones.  Address functionality first and then decide on comfort as there are lots of great options in each category.  Both over-ear headphones and in-ear headphones can be extremely comfortable, and some are better suited to certain situations than others.

I use full-size over-ear headphones at the office or when traveling, and then I use earphones or earbuds when working out or riding a motorcycle.  Really it’s up to you to decide how they will be used first and then think about if a certain set will be comfortable using them in such scenarios.

A couple of notes about this list of the most comfortable headphones.

  • This list is in no particular order as so many factors are user-dependent. It’s hard to recommend an all-encompassing solution.
  • All price points have been considered, but we have attempted to throw in an option for every budget.
  • We are open to recommendations. If you think a particular set of headphones is especially comfortable, then leave a comment below. Other readers may thank you.

List of the Most Comfortable Headphones for 2021

Bose 700 Noise Canceling Headphones

Bose 700 series noise canceling headphones
The Bose 700 is one of the most comfortable headphones on the market.

The new version of the Bose 700 is a significant upgrade in many ways to the outgoing QC35 model. However, it is now one of the most comfortable headphones on the market, thanks to some stunning ergonomic designs.

The soft and well-padded headband adjusts its clamping force to suit various head shapes, and the large well-cushioned earpads allow lots of space for the ears to breathe without making direct contact.

They are incredibly lightweight, have some of the best paddings on the market. The design is so good you can often forget that they have some of the best noise-canceling on the market and a lovely smooth, non-fatiguing sound signature.

There is a reason these headphones are used in airports all around the world. When flying, you will be using your headphones for far longer sessions than the average user, and this is the most popular model on the market.

Sony WH1000-XM4

Sony WH1000 XM4 headphones

Sonys’ new wireless noise-canceling headphones tick all the right boxes when it comes to comfort.  We were impressed by how something with so much tech inside could remain so lightweight. 

Build quality has been improved over the years, so you can forget about the cracking headband that plagued early models. The material choices make for an enjoyable experience with lots of cushioning in the earpads and the headband.

The earcups’ opening is big enough to swallow the biggest of ears, and the clamping pressure is absolutely spot on. 

They will be one of the most popular headphones this Christmas, available in plenty of colors and with bang-up to date styling.

Please read our full review of the Sony Wh-1000XM4.

Sennheiser PXC 550-II

Sennheisers most comfortable headphones.

Sennheiser has many great headphones, and for the most part, they are some of the most comfortable.

Despite being full-size over-ear headphones, the combination of light clamping pressure and breathable pads mean that they stand head and shoulders above a lot of other designs. 

Sennheiser, of course, is one of the biggest manufacturers of luxury headphones, so you get the bragging rights of owning a set.

Despite this being one of the companies’ cheaper models, they still feel like incredibly luxurious headphones once you get them in hand.

They are fully wireless, have integrated touch controls, and a fantastic 30 hours of battery life from a single charge.

Status Audio CB1

Status Audio CB-1 accessories
Status Audio CB-1 the most comfortable budget headphone on our list

I never expected to have been so impressed by the Status Audio CB-1, but after reviewing them earlier this year, there is no doubt in my mind they are a perfect addition to this list. 

Closed-back design means that they block out a lot of noise, but with generous padding to the top and bottom, these are all-day comfort headphone that is perfect for working in an office environment.

The sound quality is unmatched under $100 (Possibly even higher) its a balanced neutral-sounding earphone with solid amounts of bass and smooth-sounding natural midrange. 

They come with a set of velour pads that makes them perfect for hours of nonstop use and a generous amount of padding on the headband to boot.

Really budget-friendly they strike a great balance between sound quality, build quality, comfort, and price.

Read the Status Audio CB-1 Review

Sennheiser HD660s

Open back headphones are extremely comfortable because they allow your skin to breath

The Sennheiser HD660S is very highly regarded amongst audiophiles and continues to receive praise for its price to performance. 

In fact, in terms of pure sound to price, I would go as far as to say they are unbeatable. They consistently appear in lists of the best audiophile headphones and always hold up well when compared to headphones, many times the cost.

From a comfort standpoint, they and impeccable with big cushioned velour pads, thick headband bumpers, and an open back driver that lets your ears breathe.

We noticed that an updated version for these has just been released, and that should mean plenty of bargains to be had on the 650.

Jabra Elite 85h

If your budget can’t quite stretch to cover the cost of the Bose or Sony ANC headphones, perhaps we can tempt you with this highly competitive flagship from Jabra.

It’s a classy headphone with modern styling and clean lines, but what we liked most about them was the comfort—another full-size over-ear headphone with generous pads and thick pads. 

Build quality is excellent, and these are made for travel with excellent noise cancellation but are equally adept for home use. 

The large open earcups and soft luscious pads breath well and sit easily on the head with no pressure spots to cause irritation. They were worth the inclusion on the price alone because to remain competitive with Sony and Bose they drastically reduced the price this year which you can check out in the link below.

Blue Sadie – Best Value For Money

Formally known as the Blue Mo-fi headphones these are unique and sit very well on the head. Weird looking? Yes. Incredible sound and comfort? Also Yes. Don’t let anything put you off buying the Blue Sadie as this company is well known for its pro sound products and is used in studios around the globe.

When they hit the market back in 2014, people didn’t quite know what to make of them. From an aesthetic standpoint, the design is unique, but things start to make sense when you consider ergonomics.

Blue is one of the world’s premier makers of microphones, so they know a thing or two about audio, and their debut headphone has turned out to be a hit amongst radio presenters and podcasters alike.

More than just pads and headbands, the Mo-Fi is lightweight and has adaptable arms that seemingly mold to your head. A unique yet brilliant design.

There are some stunning deals to be had on these headphones this year and that’s why I’m listing them as the best value. Price to performance nothing comes close.

Apple Airpods Max – Best For Iphone Users

I still have a hard time calling these headphones airpods because they are a full-size set of noise-canceling cans. However, it’s hard to deny them their place as one of the most comfortable headphones this year.

Comfort is derived from some smart design choices that make them one of the airiest and least restrictive headphones on the market. A mesh canopy suspends the headband which makes them very comfortable to wear for long intervals and the earpads are a breathable fabric and memory foam that conforms to the shape of your head.

On the inside, you have seamless integration with other products in the Apple ecosystem such as iPhones, iPads, and Macs. The sound is smooth and clear whilst the ANC tech does a great job blocking out the majority of ambient noise.

The only thing we didn’t like about them was the price. We know Apple tax is a thing but unless you have your heart set on these the Bose 700 is a better choice for comfort while the Sony XM4 is a better all-round headphone for the money.

Final Audio E3000 – Most Comfortable IEM

Final Audio e3000 earphones
Final Audio e3000

When looking for comfort in-ear headphones, you want something that seems to disappear in your ears after listening for a while.  The Final Audio Design E3000 does exactly that.

These are so small and lightweight they after a while, you will forget they are even there. In fact, these are so small they are the only set of audiophile earbuds we included on our list of the best headphones for sleeping.

Apple Airpods 3rd Generations – Most Comfortable True Wireless Earbuds

Apples new Airpods 3rd Generation are our winners for the most comfortable true wireless earphones

The new 3rd generation Apple Airpods have to be given their credit when it comes to comfort. They are lightweight, wireless (so you aren’t tethered to your device) and they aren’t inserted into your ear canal. That last reason is why we have included them on this year’s list.

Most of the complaints we get about earbuds are how uncomfortable it feels to stick something in your ears. With this design, you don’t have to as they sit comfortably between the tragus and antitragus of your ears. Easy to put in and take out and have a smooth cool surface.

Tweaks to the new design include better force touch settings, smaller overall size and a slightly improved ergonomic styling allowing them to sit more securely in the ear.

Beats Studio 3

The latest Beats headphones are the best beats headphones ever made. A feature-rich stylish headphone that is instantly recognizable. Finally, the price has come down and with the Apple A1 chip working away on the inside they are actually very good value for money.

Available in a number of color options they have noise-canceling to block out external sound making them great for travel. They have a 30-hour battery life and can be quickly charged in 10 minutes to provide an additional three hours of playback. Oh and let’s not forget they are compatible with IOS and Android if you want to use voice assistance.

Comfort comes from the lightweight materials used and the soft memory foam earpads and headband that are easy on all contact points.

Audiophile On
Audiophile On is a website dedicated to high-end audio products. With over 15 years as a reviewer, all articles are hand-written by one person to allow the comparison of products. Headphones, earphones, speakers, amplifiers, or DAC's we cover here.

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