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

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I’ve been using JBL Endurance Race 2s for a bit and if you’re open to in ear they do have an audio pass through ‘aware’ mode - very good for the price, when compared to the equivalent Bose. I prefer Bose in ears for sound quality and noise cancellation, but each generation has problems. The Bose QC 2 Ultras would be my #1 best ever (if money was no object if the touch controls didn’t react to water. I’m a sweaty man and after 3-4 miles the noise cancellation controls start rotating. Shokz really are the way for true awareness. I just don’t think music sounds good through them… so I do prefer in-ear. Beats Sport lines are better than AirPod for similar tech (both owned by apple). I’d say my Beats lasted through my sweat the best of any headphones I’ve had over the years.
All I can say is avoid the JBL Endurance Race 2. Sound quality is OK, but they just aren’t very loud and not worth $75. A loud gym, you can hear almost everything even with sound canceling. Sitting somewhere quiet, they’re not bad. Not even as good as my cheap Jlab Go Air Pops.
Had the same issue. Tried 3-4 pairs, ended up with the JBL endurance race 2. I use them climbing, kayaking, and woodworking. Sound quality is great, they have never fallen out. A very secure fit but still low profile. Waterproof also adds extra peace of mind. Call quality is good too.
Currently running in JBL Endurance Race 2 earbuds and really enjoy them. They have an added eartag kinda extra stability tab that I find helpful. Good sound outside with pass through hearing in their standard presets for running modes.
the JBL endurance race 2's are good as they are heavily customizable, i.e ANC or talk through modes which take outside noise and bring it into the earbuds so you can hear it, or just disable the modes entirely and you can still hear the outside world
I have JBL Endurance Race 2 earbuds and I like them. They fit well and have an extension that works with your outer ear to lock them in place. They come with a companion app that lets you fine tune their response to gestures and voice control and have 3 modes for listening: full noise cancelling, one that allows background noise, and and voice activated background override. They are about $100 shipped from Amazon but that price varies a bit and they can be found for cheaper.

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