
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).
Anker Soundcore C30i for when i am around others but want to be able to hear what's going on around me. Anker Soundcore Life Q30 when i want total immersion, HyperX when i need chat or just want to go wired, and if i am playing in bed after my wife is asleep, i use a MusicCozy bluetooth sleep mask for comfort. https://preview.redd.it/s7al9dh2meuf1.jpeg?width=3060&format=pjpg&auto=webp&s=ff25796b5402bc95629c08d8645e7fd68e593039
Here are the ones I’ve tried. Shokz- great headphones. It sits next to your ear rather than over. Forever tethered and that can get annoying, especially if you’re wearing a high collared shirt. Shokz now has a non tethered version - I always see them returned at REI so do with that information what you will. Beats headphones - the ones that have an arm that go around your ear. I put the clip over my ear then let it dangle in front of my canal. If I want total block of ambient, I put them in like they’re intended. Three different soundcore - all very affordable especially if you get them refurbished on eBay. All controllable sound quality and controls through their app. Super super long battery life. I think I’m a soundcore person now, the ROI is just much higher with these considering their price, the way I use them, and my perceived sound quality. 1. Soundcore c30i (there are upgraded versions of it) - I really liked these they rest on the flappy part of your ear and project the sound towards the ear canal. Great sound and control. less than $50 cheap. 2. Soundcore v30i. Love these, they’re the older model but I like these because they adjust on the arm itself so you can make it more or less ambient to outside sound. Sits on top of the ear. Also less than $50 if you get them refurbished. I use these at home. 3. Soundcore Aerofit pro. I use these for work - people say I sounds great on calls and don’t hear my coworkers (I work in pretty busy and noisy office. Great sound - dare I say too great, I get overwhelmed sometimes. It sits on top of the canal so you can hear if you need to (not adjustable). These ran closer to $100 - even refurbished. They come with a strap if you want to tether them. The battery life on these are crazy - I charge once a week and I’m on those all day 5 days a week between calls and music.
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
Over-ear are bad because (a) heavy and unbalancing, and (b) you have little awareness of your surroundings. I seem to be posting this once a week now (and I promise I'm not on commission) but I absolutely love my Soundcore C30i earclips for running (I see there are C40i out now, but I've not tried them).

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