
Apple
AirPod Pro Series
Apple-integrated, great ANC but can cause ear pain.

Running these analyses costs money. Buy through my links to help keep lights on! I may get a small commission.
Take a look at the Baseus (Sound by Bose) clip style. I have sensitive ears and I've found these to be very comfortable. They sound fantastic, too. ETA: I have the Tozo ones, too. The Baseus feel much better and definitely sound better.
I like these, not the best quality but I can hear everything plus I get them for like 20 a pair on sale. I destroy earbuds so these are cheap and easy. As I said not the best sound quality, but when I’m working out they are perfect. A little tricky under a full face, but I’ve made them work for me. https://www.tozostore.com/products/openearring-headphone?variant=50682092421409&country=US¤cy=USD&utm_medium=product_sync&utm_source=google&utm_content=sag_organic&utm_campaign=sag_organic&mai_source=google&mai_medium=paid&mai_campaign=22737469657&mai_adgroup=181096780785&mai_term=&mai_content=%7Badid%7D&mai_click_id=Cj0KCQiAyvHLBhDlARIsAHxl6xpV_MT3U2-xPJ1B3fUblg1notwkd2V0UhCPu7rJfBy7YHl4KetFkHMaAiYJEALw_wcB&utm_source=ads&utm_medium=google&utm_campaign=conversion&gad_source=1&gad_campaignid=22737469657&gclid=Cj0KCQiAyvHLBhDlARIsAHxl6xpV_MT3U2-xPJ1B3fUblg1notwkd2V0UhCPu7rJfBy7YHl4KetFkHMaAiYJEALw_wcB
I have the Soundcore AeroClip and love them for their sound quality. Much of what I use open earbuds for is listening to audiobooks, YouTube videos, and the like, but the AeroClip sound good enough to use for listening to music as well, which is a wonderful bonus that has led to me using them more and more for that purpose. If I get them on my ears just right, I can wear them for a couple of hours or so before they start to hurt, but they do eventually start to feel pinchy. I also have the cheap Tozo OpenEarRing, which seems to be a little more comfortable. They are fine for audiobooks and other spoken word content but not so great for music. So, I’m wondering, for those of you who have tried a variety of clip style earbuds, which ones were the most comfortable/least pinchy, and which ones were the best combination of comfort and sound quality?
I have Tozo Open Ear Ring earbuds. AirPods were a favorite of mine too but I had the same problem as you. I can wear the Tozo ones all day without any issue because it doesn't actually sit in your ear. Not noise cancelling or anything, but they're inexpensive and super comfy.
I also wanted to mention that I wear glasses and they don't interfere with them at all, so that was one of the big reasons I went with them. The other kinds that people recommend like Shokz largely wouldn't work lol.
i have the tozo open earrings and they are great black friday bargain on amazon for only $24. it's an exellent intro to open earbuds and perfect for podcasts or connecting to your tv. i did want better sound however and bought the bose ultra earbuds on sale but could not get them to play loudly enough so i returned them. i then bought the soundcore aeroclips ($99 during black friday) and that is, for me, the sweet spot so far. they sound very good, long battery life, can be eq'd thru the app, supports ldac, and easy to connect. i also use it for phone calls and haven't had any complaints. the soundcore c50i is currently $49 and well-reviewed and may be just what you're looking for. i can also recommend the earfun open clip for the same price as the c50is. it too has good sound for the price and plays plenty loud for my needs (podcasts, tv/pc/ tablet listening).
Have to quibble, mostly because I love my mechanical watches Watch: Seiko sports 100 dive chronograph 1986 black, only one to wear it❤️ Phone: Fold6 with pitaka back and UAG folding hexagonal stand Monitor: 40$ amazon q ring. Better than Samsung app Earbuds: used to use TOZO T 10s until the changed the design, currently loving my TOZO OpenEaring Keyboard/mouse: ilogic pebble350 Flying: Bose ultra qc are great! What do you think of the Fold 8 options coming soon?

Apple
AirPod Pro Series
Apple-integrated, great ANC but can cause ear pain.

OnePlus
Buds 4
Budget king, great ANC/sound, but no wireless charging.

Anker Soundcore
Sport X20
Secure fit for sport, durable, but connectivity issues.

EarFun
Air Pro 4
Budget value, good ANC/sound, but cheap case, noisy transparency.

Beats (Apple)
Fit Pro
Workout king, secure fit, but wing-tips tear easily.

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Denon - PerL Pro

Ranked #1
Beats (Apple) - Fit Pro

Ranked #1
Sony - WF-1000XM5

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Shokz - OpenFit Series