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

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I use the Soundcore C30i by Anker. They are perfect for listening to music whilst being fully aware of your surroundings. They are very reasonably priced too. I highly recommend them.
Older fixed bridge clip-ons like soundcore c30i (my first clip-ons) can be uncomfortable after a while, but these flexible ones like the shokz opendots are super comfortable. I wear them literally all day, sometimes not even listening to anything because I just forgot about them being on. I can see how someone might prefer one or the other, but as a glasses-wearer, over-ear hooks are in the way a lot. Clip-ons work with glasses, hats, helmets etc. It sounds crazy but sometimes I put over-ear headphones over them when I'm listening to both pc and phone audio (e.g. playing a game while listening to a podcast on my phone).
I have the C30i open ear buds and they stay on with no issues. I have multiple ear piercings too and it doesnt bother me. I have small ears. https://preview.redd.it/f4lwitsmx7ug1.jpeg?width=1125&format=pjpg&auto=webp&s=c78e43e5bf0defb26ffd34e3adcbaae43bb258f7
For the smallest pairs, check out these 3 Shokz OpenDots ONE, Huawei FreeClip, Soundcore C30i. C30i is the cheapest, they're not bad. It's just not as good as the first 2. Huawei also has the FreeClip 2 coming soon. The Shokz sound the best and get the loudest. Both Shokz and and Huawei have great call quality. C30i is terrible for calls.
Everything falls out of my ears. Literally absolutely every single pair of earbuds. Apparently my concha is shallow. I recommend Soudcore c30i. Changed my life. If you want to be fancy, Bose has a similar offering.
I got sent a test pair of Soundcore's C30 open-ear earbuds. Since there's no seal, bass is almost non-existent. (unless you happen to have the perfect size ears for the sound to be aimed straight in AND close enough) And yes, you'd have to get a set with loud enough volume to defeat any ambient sound. No ANC because of no seal too.

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