
Apple
AirPod Pro Series
Apple-integrated, great ANC, but fit issues & poor Windows support.

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I have the soundcore A10 and the A30. My A10s are far more comfortable than my A30s for some reason. But they both work well and I am also a side sleeper. I do also like a bluetooth headband, I have no idea what kind I have but it is pretty comfy.
I have the soundcore sleep a10, maybe this will do? https://www.soundcore.com/products/sleep-a20-sleeping-earbuds
I got the Anker a10, had some charging issues, so I got a pair of a20s as back up, then got a 2nd pair of a20s as back up for my back up (they're still in the box). I've slept with a pair in every night for 1.5 years now and really want to make sure I never have to go without ever again.
I like my soundcore sleep a20, had to send my a10 back for lack of comfort but a20 have improved. Though can't tell for a30
Hey, I could've written this. I've owned the A10, A20 and A30 (and the Ozlos) and it's impressive how much Soundcore has improved their sleep line with each iteration.
I also use cheap Amazon headband headphones for listening to audio books while I fall asleep. I received the anker sleep earbuds as a gift but they have this weird high pitched buzzing sound that goes in and out while I’m listening to audio books (not noticeable when listening to music) that drove me nuts. So I went back to my cheap headband sleep headphones. I wear earplugs underneath to block out other sounds then turn the headphones up high so I can hear my book but not my partner’s snoring. I’m a side sleeper and they are super comfy. The battery lasts long enough that I only need to charge about once a week. Mine are LC-Dolita but look just like the ones linked above.

Apple
AirPod Pro Series
Apple-integrated, great ANC, but fit issues & poor Windows support.

OnePlus
Buds 4
Budget ANC king, but no wireless charging & windy transparency fails.

Beats (Apple)
Fit Pro
Workout secure, Apple-friendly, but wing-tips tear and case feels cheap.

Anker Soundcore
Sport X20
Value workout buds, secure fit, but connectivity can be iffy.

EarFun
Air Pro 4
Budget champ with great sound/ANC, but transparency has static.

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Technics - EAH-AZ100

Ranked #1
Beats (Apple) - Fit Pro

Ranked #1
ISOtunes - PRO Aware 2.0

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Shokz - OpenFit Series