I'm all in on headphones. Been using IEMs for a decade but the annoyances they have always ruin the experience for me. Wireless IEMs are also made to be as non-repairable as possible, so if those WF XM5s break after 2 years you'll have to buy new ones. Headphones are usually somewhat repairable.

Over-ear for me (both for wired and wireless). In-ear devices will fall off my ears every 5 minutes.

For a specific recommendation, I'd recommend the Monoprice BT600-ANC. It has really good ANC for just $100-$150, good battery life, and the sound quality of it is on par with my $70 wired headphones. You can also use it with a wire (albeit without ANC) if the battery dies.

I'd rather have over ear than iem if I had to choose. Even a cheap pair of soundcore q20s are really really decent tbh. You could get both for the price of the rather expensive xm5s

True wireless in-ears have gotten a LOT better at ANC in the last few generations. Currently, I carry the Pixel Buds Pro as my dailies, but I also have a pair of the Soundcore Liberty 3 Pros. Both are pretty great, I tend to prefer the Pixel Buds because they play nicely with my Pixel. I've been through I-couldn't-tell-you-how-many pairs of true wireless buds, and so far those two are the only ones I haven't hated wearing for extended periods. I'd give an honorable mention to the Samsung Galaxy Buds 2 Pro as well (with the caveat that some of their functionality, including factory reset, requires a Samsung device).

NB: I tend not to like the silicone ear tips, so most of the time when I buy a new pair of buds I'll buy Comply memory foam eartips. I've found they create a MUCH better seal and more confident fit. Evidently my ear canals are weirdly shaped, because no matter what brand, I seem to have trouble keeping anything in my ears and those helped.

If you got no problems with IEMs, they produce incredible sound for a fraction of the price. Just check Truthear Zero.

If you've got issues with IEMs such as ear infections due to ear wax pushed inward, then you more or less don't have a choice but to go with on-ear / over-ear. I had an infection once a decade ago and went over-ear ever since. It costs more to get good quality sound out of over-ear compared to IEMs.

I tried the XM5s and 4s and didn't care for either of them. They wouldn't stay in while I was moving around, relaxing, eating etc.

So I started looking at alternatives for both in and over ear pods. Settled on the OWS Pro for pods that don't go in the ear but sit outside it and Logitech zone true wireless for in ear. The zones I got for about 200 on sale and like a lot, but the real winner has been the OWS pros which come with a 16 hour battery life which lets me wear them through the night. I liked them so much I bought a second pair for when the first are charging haha.

If you're itching more towards to the over-ear one, I can personally recommend the q45 and q35.

Lots of good comments here so we'll keep this up, but I'll flag rule 2 in the sidebar. Open-ended general discussions are welcome here, but we ask that recommendation requests and those seeking advice be posted to !askandroid@lemdro.id instead. Thanks!

Ok so I had the CH700N's. I also then had some AirPod Pros for a year. I recently upgraded to the Sennheiser Momentum 4 over-ear and the Sony WF-1000XM5's, but I also bought and returned the WF-XM4s, Bose QCII in-ear, and the Sennheiser Momentum TW3.

Every single pair of in-ear wireless earbuds I've tried that aren't AirPods Pro suck. I am still using the XM5s but their multipoint sucks so I had to disable it, and they drop out for a split second every 10 or so mins. The XM4s were similar but incredibly painful to wear. The QCII were similar to the XM5s. The Sennheiser TW3 connection quality was dog shit - putting a few fingers around an earbud would break their connection with each other.

As for over-ears, my Sennheiser Momentum 4s are pretty good - they sound great, feel pretty comfortable, last for ages, and do not suffer any connectivity issues in my experience.

But to be honest, I've reached the point where if phones still just had bloody headphones jacks I'd use wired over-ears. I'd probably still use AirPods Pro for portability once I move back to iOS though, but I could also see myself going wired there too to avoid the whole wireless hassle and cost.

So my conclusion is over-ear for every possible reason except absolute portability.

I also would recommend against the Sony WH-1000XM5 over-ear because they feel so cheaply made it's a joke.

As far as price/performance ratio, iems are unbelievable. I used to be an over-ear purist but the quality of iems have blown me away that I've moved over almost completely. I keep a pair of high quality iems at my desk for listening/daily use at my computer, and a pair of galaxy buds 2 are my knock-arounds for daily use while out and about, doing chores, or even while sleeping (foam tips make them remarkably good as both earplugs and also for listening to whatever helps you fall asleep)

I'd recommend against Sony IEMs. I know multiple people who got theirs replaced under warranty (WF-1000XM4 and 5), one of them twice. They tend to not last for very long.

I have some WH-1000XM4 over-ears and they're not terrible, but not worth the money either. They need an equalizer to sound decent.

But before you buy anything: Can you wear IEMs comfortably for a long time? I got some weirdly shaped ears and horrible earwax, so I don't bother with those at all.

I have both in ear XM4 and over ear XM5s and I don’t like either. The xm4 is just too big and too heavy. It feels like it’s barely hanging onto my ear. I’ve tried using the for running or bike riding and they fall out. If you try to force them to stay in your ear it can wedge itself in too tight and get painful.

The XM5s are too tight and they hurt right below my ear if I wear them too long. The anc is good but I had some Bose QC35s before and they were waaay more comfortable and worked just as good.

I wish I had got the AirPods Pro and whatever new quiet comfort headphones Bose had now. Still thinking of switching.