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

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I have a pair of Tozo openearrings that have been absolutely killer. Super open and clear with great sound and enough bass to keep you happy. Not invisible because mine are black but I believe they have a more skin toned option. They generally just look like a larger earring at a casual glance which is pretty cool though!
I've been super surprised with how comfortable they are. They're super super light and you forget they're on after like 10 minutes. It took maybe a few days of getting used to the fit but after that they're easily the most comfortable earbuds I've ever owned
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?
Listening to audiobooks (and sometimes YouTube videos) is the main thing I do with my open earbuds, but I mainly use them around the house or when when I’m waiting for an appointment somewhere, so not in noisy environments. I wouldn’t expect them to be good for use in noisy settings. I have the Soundcore AeroClip, which is excellent and also good enough to use for music, and the Tozo OpenEarRing, which is ok for spoken media but not so great for music.
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).

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