The Best Headphones for People Who Wear Glasses

Finding the best headphones for people who wear glasses may seem like an impossible task. Glasses and headphones go together like cats and dogs, or fire and water, or… well, you get it. And yet you experience the same annoyances every day. From poorly fitting ear cups to bands that pinch and put pressure on frames, we’ve seen it all. That’s why it was finally time to stop the madness and put together an honest roundup of the best products that make an effort to solve the issue.

The Best Headphones for People Who Wear Glasses

Roundup: The best headphones for people who wear glasses

We’re looking to accomplish a few things in this review, including get you set up in a pair of headphones that accommodate glasses. To get the job done, we’re going to evaluate using the following criteria:

  • Comfort. Our top pick should allow you to wear glasses for an extended period of time without discomfort. That means that everything from the ear cups to the pressure placed on your head have to be perfect. Frames should fit snugly and without any pinching, rubbing, or other pains.
  • Sound quality. The next order of business is picking headphones that sound as good as they feel. After all, what good are headphones that feel great if they sound like garbage? At that point you’re wearing a fancy (and expensive) headband.
  • Utility. The best headphones for people who wear glasses have to do more than just be comfortable. No features of modern headphones should be sacrificed, including making and receiving calls,  on-headset controls, and great battery life.

Without further ado, let’s get into the list!

ContextAudio Bluetooth 5 Earbuds are the best true wireless earbuds for people who wear glasses $119.99

Best earbuds for wearing glasses

ContextAudio Bluetooth 5 True Wireless Earbuds $119.99 at endive.com

ContextAudio’s next generation of wireless earbuds have a lot to offer, including reduced power consumption, stronger signal strength, and a host of other enhancements thanks to new Bluetooth 5 chipsets. And when it comes to glasses friendly headphones there’s nothing more comfortable than true wireless earbuds that don’t come in contact with your frames or put pressure on ears.

Next-gen Bluetooth 5 tech delivers. 30% longer battery life, near perfect sound quality, and seamless switching from calls to music to voice commands. ContextAudio shines as one of the first products to include these new features. You can read more about the specifics behind Bluetooth 5 here.

Comfort during long wear with glasses. The promise of true wireless earbuds is great in theory, but has not been perfectly executed in the past.

Included charging case quadruples battery life while on the road. The handy charging case not only keeps your earbuds safe when not in use, but includes a battery for additional charging. Every time you put them away, you get an extra rapid charge – effectively multiplying active use time by 4x.

Optional sports mode with ear clips. If you’re concerned about true wireless earbuds falling out (we are too) you’ll be glad to know that low profile ear clips are included as option attachments. These actually work well with glasses if you choose to work out in them, and are perfect for additional security during intense movement.


Sennheiser HD 4.40 Around Ear Bluetooth Wireless Headphones are the best headphones for people who wear glasses $82.49Sennheiser glasses friendly headphones

↗️ VIEW AT AMAZONSennheiser HD 4.40 Around Ear Bluetooth Wireless Headphones $82.49 at Amazon.com

Sennheiser is one of the most respected names in sound, which makes it appropriate they make the top of our glasses friendly headphones list. Over ear headphones need to have a lot of “give” in the ear cup material to ensure comfort over long wear sessions. The HD 4.40 are everything we expect from a legacy brand with some perks for glasses wearers. Check out the highlights:

Large, soft ear cups. The HD 4.40’s ear cups are extra soft and will conform perfectly to the frames of your glasses no matter their position. Once you get used to the feeling, you won’t even notice.

Clean, clear sound. You’ll enjoy the reputation Sennheiser has earned as a premium headphones brand every time you turn on the HD 4.40s.

All the bells and whistles. Bluetooth 4.0 wireless connectivity with AptX means you’re cord free. Ear-cup mounted controls for changing tracks and for making calls via the integrated microphone. That said, if you need or want the cord it’s also included. Combined with a 25 hour battery life and much more in standby time and you’ll be seeing and hearing clearly.


Bose QuietComfort 35 Series II offer glasses-friendly design and best in class operation $349.00

glasses friendly headphones

Bose QuietComfort 35 Series II $349.00 at Amazon.com

Bose quality engineering. The name Bose is pretty much synonymous with top quality (and top pricing, more on that later). With the QuietComfort 35 Series II you’ll find that same pitch-perfect sound and high quality construction.

Super squishy memory foam ear cups. Bose took their time making these over ear headphones. It’s particularly evident in the ear cups, with squishy memory foam style material that conforms to ears without putting pressure on your glasses’ frames.

Industry-leading noise canceling technology. Even though less expensive noise canceling models exist, Bose maintains it’s lead as the best in the business for active noise canceling (ANC) headphones. Keep in mind that switching on ANC mode will drain battery much faster than when it is turned off, and that you won’t be able to hear much outside your music. While that’s the point, it shouldn’t be used during commutes or when you may need to be listening for ambient sounds.

Expensive. Bose has a leading reputation for making some of the best headphones – and for pricing them at the very top of the market. The QuietComfort 35 Series II are no different, and come in far above many models that are just as comfortable for people with glasses. Depending on what you need, this may or may not deter you from the Bose brand.


Headphones Friendly Glasses Questions and Answers

How are you supposed to wear glasses with headphones?

Very carefully! In all honesty, the headphones or earbuds you select should be based on the type of glasses you own as well as the shape of your head. Everybody is unique, and so we selected headphones that we thing will work for most people. In the end, the only way to be truly comfortable is to get a pair and try them out. Of the options we listed above, the general consensus that true wireless earbuds are the best solution, as they do not interfere with glasses in any way, and are most likely to

What is the best gaming headset for people with glasses?

Gaming headsets for people who wear glasses are a different animal. They need to be comfortable and wearable with glasses for hours on end, and fall outside the current scope of our review. We looked at headphones that would be good for listening to music, podcasts, and other activities that take a few hours at a time. In addition, our headphones do not include a boom mic, common in gaming headsets. We’ll cover these in a future review.

Are there any headphones that are comfortable with glasses?

If you’re not finding what you need in this article, or have tried a number of headphones without success, you may need to look at solutions that don’t touch your ears or head whatsoever. We’ve heard of people who just can’t wear headphones or earbuds at all because they are painful or uncomfortable. There are a number of options we have covered in other reviews, and you can start here.