T6 Truly Wireless

Second this. I used the Tozo T6 and the only reason I had to move on was cause I lost one. Made the switch to the Soundcore R50i NC and they are great for the budget. NC is basic but makes for a good entry point into NC

I'm on my second set of TOZOs and I don't remember how many years I had the first set (T6, $25). I may have killed them though, they got washed accidentally. They still worked for a year after that, but it may have contributed. The rest of my family has had their T6 sets working fine for years. I upgraded to the NC7 ($30) and they've been great for the last 2 years.

That was going to be my goto recommendation - "offbrand headphones". Unless there are must-have features, I would go with anything cheap (and therefore replaceable). For your particular need, "Kurdene" on amazon are the smallest I've used. I also like "Tozo" T6 (Amazon is ergonomic-only, but their website should still have non-ergo symmetrical ones, so you have used either in either ear). Everything I use has IPX7 or IPX8 (probably not official certification, but I shower with them no problem), but you won't find anything cheap with a physical button. At least Tozo has an app in which you can change the tap functionality. EDIT: the tldr is search for "ipx7/8 headphones" on Amazon \*and\* eBay. You'll get a bunch of no-name buds with RGB boxes and a million hours of battery. I would focus less on the dumb features and more on what fits your life. And again, easier to trash a $20 set.

I also found the jlabs uncomfortable/painful. Returned them and ordered the tozo t6 which are the best fitting earbuds I've tried, might fit you well too!

For the gym, I like something basic that I don't care if it dies from sweat and other abuse. To that end, I got the tozo open ear and tozo t6. T6 to block out sound and open ear when outside and I want to hear cars and stuff. Both of these are in the 20 to 30 dollar range.

Are you wanting sound or noise canceling? For the latter, I use foam construction earplugs. They are soft and comfortable to sleep in, and cancel out any noise I need. (Mainly birds early in the morning since our neighbor put a birdhouse right outside our bedroom window.) For sound, I've fallen asleep with my TOZO T6 buds in a few times and didn't wake up with any pain or soreness.

Tozo t6. Water resistant and resilient. I ran over one of the earbuds with my truck, and it still worked. And only $25. So, it's not a big loss if something happens. Pro tip don't get the black ones. If you drop one, you may never find it.