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

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I have the original OpenFit and wear them with sunglasses any time I run outside. Never had any problems with it. Wouldn't wear them in the gym tho, I've got noise cancelling earbuds for that.
I’m gonna say something controversial. After trying the Shockz 1 and thinking they weren’t loud enough and then again trying the 2s and having the same issue. I have given up on them. I honestly just bought two cheap pairs of Tozo open ear headphones from Amazon and I love them. They are incredibly comfortable, and quite a bit louder. The louder volume was specially useful for those of you that are into podcasts. Or if part of your run is down bus streets. You can still hear everything outside of you very well but having the option to higher volume is great. I’ve used these for several 50ks and 100ks. Hope this helps!
The most basic shokz model. I have no issues wearing them with sunglasses and a hat or headband over my ears in winter.
Yep, Shokz OpenFit Pro here. The bit of noice cancelling they offer while being open ear is a nice bonus. Used OpenFit 1 and 2 as well. Used their bone conduction line beforehand also.
I’m really disappointed in my new OpenRun pros. Volume is so low that I often turn them off mid run. My older original Shokz had much better volume.
I have the Sony WF-1000XM5 and the first generation of the Shokz Openfit. I basically only use the Shokz. I feel stupid for buying the Sonys a few months earlier because I have hardly used 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