Wearing glasses under headphones is annoying. If you’re like me, the headphones press the arms of the glasses into the sides of your head and you get a headache after about half an hour. Here’s what I found makes this combo less awful.
1. Get glasses with BIGGER (not smaller) arms
All the advice I’ve found on the internet says to find glasses with arms that are smaller, thinner and less obtrusive, as these will impact you less. Based on the anecdotal evidence from myself and the one friend I asked, this isn’t true – we each have a pair of glasses with thin arms and one with thick, and we both prefer the thicker arms to wear under headphones.
Physics backs us up here.
Pressure is the force on an object that is spread over a surface area. For a given amount of force, the pressure (how hard that force is pressing on each point of the surface) will be higher if that surface area is smaller.
You can test this yourself. Put your hand flat against the side of your head and press hard. Pretty comfy, probably. Now, put a fingertip against your head like you’re going to poke yourself in the cheek or above your ear, and press with the same amount of force. Hurts more, right? The force is the same, but the pressure is higher because the surface area is smaller. You can also test this if you’re giving someone a back massage – you can press on someone’s scapula comfortably with a flat hand, but you’ll notice a very different response if you exert the same force with your elbow.
It’s similar for glasses. They exert force on the side of your skull, especially when squeezed on by headphones. For thinner arms, this force is more concentrated, so the pressure is higher. In contrast, thicker arms distribute the same force over a slightly bigger surface area, so there’s less pressure on any particular spot.
2. Get headphones that squeeze less
Some headphones squeeze your head tighter than others. Try to find headphones that are less squeezy (or ones with softer padding). I’d recommend heading to an electronics shop or game shop and trying on every set of headphones in the display to see what you like. “Squeeziness” is not usually a listed metric in the specs provided by online stores.
3. Avoid the problem altogether
Earbuds
Standard in-ear earbuds (of the wired or Bluetooth variety) solve this issue altogether. Make sure they aren’t the ones that loop over your ears for security or whatever – I’m told it feels weird to wear glasses with the arms sitting on the earbud loop bits.
Choose another space
Depending on the reason you’re wearing headphones, you could do the following:
- Find a space you can work alone so you can play music/meetings/rain sounds/transcripts out of a speaker.
- Work somewhere quiet enough that you don’t need headphones to block out noise/chatty coworkers.
- Work somewhere that naturally generates your focus music, like visiting a cafe for the background noise.
Contacts or laser eye surgery
Then at least you don’t have to wear glasses? I know nothing about either of these options, it just seemed better to have an exhaustive list of the things one could fix.
4. Alter your headphones
I’ve seen internet sources explaining (though not especially recommending) you just cut into the headphones where the glasses sit so the padding doesn’t press there. The good folks at Headphonesty are kind enough to provide us with this “Caution: Contents Hot”-level warning:

I can’t think of a way this would be beneficial or successful, for several reasons (notably the integrity of the headphone padding and noise bleed) but if you’ve figured it out, I’d love to hear about it. We could make millions.