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

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OP said ANC is a must... You're clowning. I have a set of Openfit 2 and they're great, but they are the literal opposite of noise cancelling. (Sure the upcoming "Pro" is supposed to have some kind of ANC, but I haven't seen those in the wild and whether it works well is an "open" question.)
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!
OpenFit2 by Shockz are absolutely incredible. So comfortable I forget I’m wearing them
I can't use any headphones while running that do not have a strap going around my head or my ears. Currently I use Shokz 2 for running because I like that I can hear outside noise with them. They're great and I would recommend them.
I vehemently disagree with your call quality rating. Open dots sound like a reverb far away hall way with no lower tones and thr aero line both clip and fit2 sound way more professional and office acceptable.
I really enjoy my Shockz openfit 2, but they are out of your price range. I do suggest looking at other open ear buds like it though and find one you like. Those clip on ones are ok also, but they annoy me to wear.

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